Pub Date : 2025-10-02Epub Date: 2025-09-25DOI: 10.1080/00397911.2025.2564411
Amogh R. Kulkarni (Methodology) , Mahesha Kumaraswamy (Funding acquisition) , Turuvekere K. Chaitra (Funding acquisition) , Doddahosur M. Gurudatt (Funding acquisition) , Kanchugarakoppal S. Rangappa (Supervision) , Toreshettahally R. Swaroop (Supervision Writing – original draft) , Basappa Basappa (Supervision)
In this article, we disclose a regiospecific condensation of methyl ketones with S-methyl O-phenyl carbonodithioate in the presence of sodium hydride in DMF for the synthesis of β-oxodithioesters. The present method is easy and efficient with respect to yield and substrate scope. A probable mechanism of formation of β-oxodithioesters is also given. Our approach overcomes limitations such as commercially discontinued substrates, difficulties in preparing thionating substrates, lengthy synthetic steps and requirement of high temperatures.
{"title":"Sodium hydride induced condensation of methyl ketones with S-methyl O-phenyl carbonodithioate: a regiospecific synthesis of β-oxodithioesters","authors":"Amogh R. Kulkarni (Methodology) , Mahesha Kumaraswamy (Funding acquisition) , Turuvekere K. Chaitra (Funding acquisition) , Doddahosur M. Gurudatt (Funding acquisition) , Kanchugarakoppal S. Rangappa (Supervision) , Toreshettahally R. Swaroop (Supervision Writing – original draft) , Basappa Basappa (Supervision)","doi":"10.1080/00397911.2025.2564411","DOIUrl":"10.1080/00397911.2025.2564411","url":null,"abstract":"<div><div>In this article, we disclose a regiospecific condensation of methyl ketones with <em>S</em>-methyl <em>O</em>-phenyl carbonodithioate in the presence of sodium hydride in DMF for the synthesis of β-oxodithioesters. The present method is easy and efficient with respect to yield and substrate scope. A probable mechanism of formation of β-oxodithioesters is also given. Our approach overcomes limitations such as commercially discontinued substrates, difficulties in preparing thionating substrates, lengthy synthetic steps and requirement of high temperatures.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 19","pages":"Pages 1464-1470"},"PeriodicalIF":1.8,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145340704","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-02Epub Date: 2025-07-12DOI: 10.1080/00397911.2025.2529464
Soukhyarani Gopal Nayak (Conceptualization Data curation Formal analysis Funding acquisition Investigation Writing – original draft Writing – review & editing) , Vishwa B. Das (Resources Writing – review & editing) , Vinuta Kamat (Writing – review & editing) , Venuprasad K. D. (Writing – review & editing)
Background
Cancer remains one of the leading causes of death worldwide. Several factors contribute to the development of cancer. Current cancer treatments primarily involve chemotherapy, radiotherapy, surgery, immunotherapy, and targeted therapies such as kinase inhibitors. While these treatments have been used for various types of cancer, they often fall short of providing a complete cure. The limitations of existing treatments include inherent drug resistance, systemic toxicity, severe side effects, low efficacy, and poor solubility. These challenges underscore the need for new therapeutic approaches.
Objective
1. Identification of new targets and development of more effective drugs
2. Overcoming drug resistance and minimizing toxicity and side effects
3. Improving drug solubility and bioavailability
Methods and Results
One promising avenue is the development of heterocyclic-based anticancer agents. These compounds, have demonstrated potential in preclinical and clinical studies. This study aims to review the latest advancements in heterocyclic anticancer agents and examine the structure-activity relationships (SAR) of the most potent compounds, shedding light on how modifications to their chemical structures can enhance their anticancer efficacy and minimize side effects.
Conclusion
The development of anticancer agents has made significant strides in recent years, with numerous compounds demonstrating promising potential in preclinical and clinical studies.
{"title":"Advances in the development of potent heterocyclic anticancer agents: a critical review","authors":"Soukhyarani Gopal Nayak (Conceptualization Data curation Formal analysis Funding acquisition Investigation Writing – original draft Writing – review & editing) , Vishwa B. Das (Resources Writing – review & editing) , Vinuta Kamat (Writing – review & editing) , Venuprasad K. D. (Writing – review & editing)","doi":"10.1080/00397911.2025.2529464","DOIUrl":"10.1080/00397911.2025.2529464","url":null,"abstract":"<div><h3>Background</h3><div>Cancer remains one of the leading causes of death worldwide. Several factors contribute to the development of cancer. Current cancer treatments primarily involve chemotherapy, radiotherapy, surgery, immunotherapy, and targeted therapies such as kinase inhibitors. While these treatments have been used for various types of cancer, they often fall short of providing a complete cure. The limitations of existing treatments include inherent drug resistance, systemic toxicity, severe side effects, low efficacy, and poor solubility. These challenges underscore the need for new therapeutic approaches.</div></div><div><h3>Objective</h3><div><ul><li><span></span><span><div>1. Identification of new targets and development of more effective drugs</div></span></li><li><span></span><span><div>2. Overcoming drug resistance and minimizing toxicity and side effects</div></span></li><li><span></span><span><div>3. Improving drug solubility and bioavailability</div></span></li></ul></div></div><div><h3>Methods and Results</h3><div>One promising avenue is the development of heterocyclic-based anticancer agents. These compounds, have demonstrated potential in preclinical and clinical studies. This study aims to review the latest advancements in heterocyclic anticancer agents and examine the structure-activity relationships (SAR) of the most potent compounds, shedding light on how modifications to their chemical structures can enhance their anticancer efficacy and minimize side effects.</div></div><div><h3>Conclusion</h3><div>The development of anticancer agents has made significant strides in recent years, with numerous compounds demonstrating promising potential in preclinical and clinical studies.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 19","pages":"Pages 1437-1463"},"PeriodicalIF":1.8,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145340706","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Building upon previous research on hydrazone-bearing aryloxyacetic acid derivatives, a novel series of 5-nitroguaiacol-based hydrazones (3a–l) was synthesized and characterized spectroscopically. Their in vitro cytotoxic effects were evaluated against human non-small cell lung cancer (A549) and normal bronchial epithelial cell lines (BEAS-2B) using the MTT assay. Compounds 3d and 3k exhibited selective and potent cytotoxicity (IC50 = 10.24 µM and 4.99 µM, respectively) and strong aldolase A (ALDOA) inhibition at 10 µM (89.89% and 75.19%). Further mechanistic studies revealed that both compounds decreased HIF-1α expression and modulated apoptotic pathways by upregulating Bax and downregulating Bcl-2 protein levels. Molecular docking studies supported the experimental findings, demonstrating significant interactions of 3d and 3k with key residues in ALDOA, Bax, and Bcl-2, suggesting a dual mechanism involving glycolysis inhibition and apoptosis induction. These results indicate that 3d and 3k are promising lead compounds for targeted lung cancer therapy.
{"title":"Dual action of novel 5-nitroguaiacol-based hydrazones: Targeting aldolase-a and inducing apoptosis in lung cancer","authors":"Mürvet Tümenci (Formal analysis Funding acquisition Investigation Methodology Resources Validation Visualization Writing – original draft) , Burçin İrem Abas (Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , Bensu Kozan (Data curation Formal analysis Methodology Resources Validation Visualization Writing – original draft Writing – review & editing) , Özge Çevik (Conceptualization Formal analysis Methodology Validation Visualization Writing – original draft Writing – review & editing) , Necla Kulabaş (Investigation Methodology Resources Software Validation Writing – original draft Writing – review & editing) , Faika Başoğlu (Software Validation Visualization Writing – original draft Writing – review & editing) , Sevil Şenkardeş (Conceptualization Data curation Funding acquisition Investigation Methodology Project administration Supervision Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2568472","DOIUrl":"10.1080/00397911.2025.2568472","url":null,"abstract":"<div><div>Building upon previous research on hydrazone-bearing aryloxyacetic acid derivatives, a novel series of 5-nitroguaiacol-based hydrazones (<strong>3a–l</strong>) was synthesized and characterized spectroscopically. Their <em>in vitro</em> cytotoxic effects were evaluated against human non-small cell lung cancer (A549) and normal bronchial epithelial cell lines (BEAS-2B) using the MTT assay. Compounds <strong>3d</strong> and <strong>3k</strong> exhibited selective and potent cytotoxicity (IC<sub>50</sub> = 10.24 µM and 4.99 µM, respectively) and strong aldolase A (ALDOA) inhibition at 10 µM (89.89% and 75.19%). Further mechanistic studies revealed that both compounds decreased HIF-1α expression and modulated apoptotic pathways by upregulating Bax and downregulating Bcl-2 protein levels. Molecular docking studies supported the experimental findings, demonstrating significant interactions of <strong>3d</strong> and <strong>3k</strong> with key residues in ALDOA, Bax, and Bcl-2, suggesting a dual mechanism involving glycolysis inhibition and apoptosis induction. These results indicate that <strong>3d</strong> and <strong>3k</strong> are promising lead compounds for targeted lung cancer therapy.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 19","pages":"Pages 1471-1484"},"PeriodicalIF":1.8,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145340703","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A pseudo seven component double Ugi reaction of isocyanide, aniline, benzoic acid, and 2,2’-(hexane-1,6-diylbis(oxy)) dibenzaldehyde in MeOH solvent under reflux has been reported. This pseudo-seven-component reaction under mild reaction conditions led to the synthesis of pharmaceutically important and structurally interesting bis- carboxamide products. The reaction with tert-butyl isocyanide is diastereoselective (5a–h), while with cyclohexyl isocyanide the diastereoselectiveness depends to the substitution on the benzoic acid. Benzoic acid with electron-donating substituents leads to diastereoselectiveness (5i–k), and with benzoic acid with electron-withdrawing substituents each pair of diastereomers is formed (5l–r). Numerous analytical methods, including 1H-NMR,13C-NMR, and FT-IR, are used to validate the chemical structures of the products.
{"title":"Pseudo-seven-component double Ugi reaction with 2,2’-(hexane-1,6-diylbis(oxy))dibenzaldehyde for the synthesis of bis- carboxamides","authors":"Afagh Banifereydani (Data curation Validation Writing – original draft) , Hossein Nasr-Isfahani (Conceptualization Methodology Project administration Resources Supervision Visualization Writing – review & editing) , Mohammad Bakherad (Conceptualization Investigation Methodology) , Afshin Sarvary (Data curation Formal analysis Validation Writing – review & editing)","doi":"10.1080/00397911.2025.2572083","DOIUrl":"10.1080/00397911.2025.2572083","url":null,"abstract":"<div><div>A pseudo seven component double Ugi reaction of isocyanide, aniline, benzoic acid, and 2,2’-(hexane-1,6-diylbis(oxy)) dibenzaldehyde in MeOH solvent under reflux has been reported. This pseudo-seven-component reaction under mild reaction conditions led to the synthesis of pharmaceutically important and structurally interesting bis- carboxamide products. The reaction with <em>tert</em>-butyl isocyanide is diastereoselective (<strong>5a–h</strong>), while with cyclohexyl isocyanide the diastereoselectiveness depends to the substitution on the benzoic acid. Benzoic acid with electron-donating substituents leads to diastereoselectiveness (<strong>5i–k</strong>), and with benzoic acid with electron-withdrawing substituents each pair of diastereomers is formed (<strong>5l–r</strong>). Numerous analytical methods, including <sup>1</sup>H-NMR,<sup>13</sup>C-NMR, and FT-IR, are used to validate the chemical structures of the products.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 19","pages":"Pages 1491-1500"},"PeriodicalIF":1.8,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145340705","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-10-02Epub Date: 2025-10-08DOI: 10.1080/00397911.2025.2568479
Mehul V. Makwana (Conceptualization Data curation Formal analysis Investigation Validation Writing – original draft Writing – review & editing) , Richard F. W. Jackson (Conceptualization Formal analysis Funding acquisition Investigation Methodology Project administration Resources Supervision Validation Writing – review & editing) , Richmond Muimo (Conceptualization Formal analysis Funding acquisition Investigation Project administration Resources Supervision Writing – review & editing)
Stable phosphohistidine (pHis) analogues which can be incorporated into peptides are valuable tools for the study of pHis in a biological context. The phosphopyrazolyl side chain has proved useful in the generation of selective τ-pHis antibodies. To allow potential incorporation of the phosphopyrazolyl side chain to peptides a N-Fmoc dibenzyl pyrazole phosphonate building block 3 was synthesized. N-Fmoc dibenzyl pyrazole phosphonate 3 was accessible in four synthetic steps using the Hirao cross coupling reaction via a P-aryl bond formation, and Vederas Boc-β-lactone 11 opening reaction to give the protected amino acid.
{"title":"Synthesis of a N-Fmoc dibenzyl pyrazolyl phosphonate protected τ-phosphohistidine building block for Fmoc SPPS","authors":"Mehul V. Makwana (Conceptualization Data curation Formal analysis Investigation Validation Writing – original draft Writing – review & editing) , Richard F. W. Jackson (Conceptualization Formal analysis Funding acquisition Investigation Methodology Project administration Resources Supervision Validation Writing – review & editing) , Richmond Muimo (Conceptualization Formal analysis Funding acquisition Investigation Project administration Resources Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2568479","DOIUrl":"10.1080/00397911.2025.2568479","url":null,"abstract":"<div><div>Stable phosphohistidine (pHis) analogues which can be incorporated into peptides are valuable tools for the study of pHis in a biological context. The phosphopyrazolyl side chain has proved useful in the generation of selective τ-pHis antibodies. To allow potential incorporation of the phosphopyrazolyl side chain to peptides a N-Fmoc dibenzyl pyrazole phosphonate building block <strong>3</strong> was synthesized. N-Fmoc dibenzyl pyrazole phosphonate <strong>3</strong> was accessible in four synthetic steps using the Hirao cross coupling reaction via a P-aryl bond formation, and Vederas Boc-β-lactone <strong>11</strong> opening reaction to give the protected amino acid.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 19","pages":"Pages 1485-1490"},"PeriodicalIF":1.8,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145340707","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-17Epub Date: 2025-09-11DOI: 10.1080/00397911.2025.2558714
Tarik E. Ali (Conceptualization Funding acquisition Investigation Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Resources Software) , Ali A. Shati (Formal analysis Software Visualization) , Mohammad Y. Alfaifi (Formal analysis Software Visualization) , Serag E. I. Elbehairi (Formal analysis Investigation Methodology Software Validation)
One-pot synthetic strategy was designed for the synthesis of novel diethyl (pyrazolo- [4,3-c]quinolin-3-yl)phosphonates and diethyl (isoxazolo[4,5-c]quinolin-3-yl)phosphonate. The novel phosphorus heterocycles of types 1,4,2-diazaphospholes, 1,4,2-oxazaphosphinines and 1,4,2-diazaphosphinines containing 4-quinolinone ring were also achieved. The designed strategies depended on a three component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (1) with a series of bi-nucleophilic nitrogen reagents in the presence of diethyl phosphite under solvent-free and catalyst-free conditions. This newly developed approach helped to synthesize new ten organophosphorus compounds with good yields. The IR, MS and NMR spectroscopic tools were used to characterize the isolated compounds, and their formation mechanisms were discussed. All synthesized compounds were evaluated for their in vitro cytotoxicity against A549, MDA-MB-231 and HeLa cell lines. Compounds 10 and 11 exhibited the most potent cytotoxicity, in comparison with doxorubicin. Furthermore, these two compounds significantly induced early apoptosis and reducing cell viability in the studied tumor cells. Additionally, both compounds 10 and 11 demonstrated promising ability to arrest the cell cycle at the S and G2 phases. In silico ADMET predictions indicated that compounds 10 and 11 possess higher predicted human intestinal absorption (∼89.6% vs. 51.85% for doxorubicin), absence of AMES mutagenicity, and lower predicted acute and chronic oral toxicities in rats. Potential hepatotoxicity and CYP enzyme inhibition were also observed. Molecular docking against EGFR-T790M/V948R revealed that both compound 10 and 11 exhibited a binding affinity of −8.4 and 8.9 kcal/mol, respectively. The interactions of both compounds with key amino acid residues (e.g., LEU 718, VAL 726, ALA 743, MET 790, ASP 855) were consistent with their strong in vitro cytotoxic activity against A549 (EGFR-mutated) cells, supporting their potential as EGFR-targeted anticancer agents.
设计了一锅法合成新型（吡唑啉- [4,3-c]喹啉-3-基）膦酸二乙酯和（异恶唑啉[4,5-c]喹啉-3-基）膦酸二乙酯。还获得了1,4,2-二氮磷孔型、1,4,2-恶氮磷和含4-喹啉酮环的1,4,2-二氮磷的新型磷杂环。设计的策略依赖于在无溶剂和无催化剂的条件下，4-氧-1,4-二氢喹啉-3-甲醛(1)与一系列双亲核氮试剂在亚磷酸二乙酯存在下的三组分反应。这种新方法有助于合成新的十种有机磷化合物，收率高。利用红外光谱、质谱和核磁共振光谱对分离得到的化合物进行了表征，并对其形成机理进行了探讨。所有合成的化合物对A549、MDA-MB-231和HeLa细胞株的体外细胞毒性进行了评价。与阿霉素相比，化合物10和11表现出最强的细胞毒性。此外，这两种化合物显著诱导肿瘤细胞早期凋亡和降低细胞活力。此外，化合物10和11都显示出在S期和G2期阻止细胞周期的能力。ADMET预测表明，化合物10和11具有较高的预测人体肠道吸收（~ 89.6%，而阿霉素为51.85%），没有AMES诱变性，并且在大鼠中具有较低的预测急性和慢性口服毒性。潜在的肝毒性和CYP酶抑制也被观察到。与EGFR-T790M/V948R的分子对接表明，化合物10和11的结合亲和力分别为−8.4和8.9 kcal/mol。这两种化合物与关键氨基酸残基（如LEU 718， VAL 726, ALA 743, MET 790, ASP 855）的相互作用与它们对A549 （egfr突变）细胞的强体外细胞毒活性一致，支持它们作为egfr靶向抗癌药物的潜力。
{"title":"Synthesis and anticancer evaluation of novel azoloquinolinyl phosphonates, 1,4,2-Diazaphospholes, 1,4,2-Oxazaphosphinines, and 1,4,2-Diazaphosphinines containing a 4-quinolinone ring: Cytotoxicity, apoptosis, cell cycle analysis, In silico ADMET, and molecular docking studies","authors":"Tarik E. Ali (Conceptualization Funding acquisition Investigation Writing – original draft Writing – review & editing) , Mohammed A. Assiri (Formal analysis Resources Software) , Ali A. Shati (Formal analysis Software Visualization) , Mohammad Y. Alfaifi (Formal analysis Software Visualization) , Serag E. I. Elbehairi (Formal analysis Investigation Methodology Software Validation)","doi":"10.1080/00397911.2025.2558714","DOIUrl":"10.1080/00397911.2025.2558714","url":null,"abstract":"<div><div>One-pot synthetic strategy was designed for the synthesis of novel diethyl (pyrazolo- [4,3-c]quinolin-3-yl)phosphonates and diethyl (isoxazolo[4,5-c]quinolin-3-yl)phosphonate. The novel phosphorus heterocycles of types 1,4,2-diazaphospholes, 1,4,2-oxazaphosphinines and 1,4,2-diazaphosphinines containing 4-quinolinone ring were also achieved. The designed strategies depended on a three component reaction of 4-oxo-1,4-dihydroquinoline-3-carboxaldehyde (<strong>1</strong>) with a series of <em>bi</em>-nucleophilic nitrogen reagents in the presence of diethyl phosphite under solvent-free and catalyst-free conditions. This newly developed approach helped to synthesize new ten organophosphorus compounds with good yields. The IR, MS and NMR spectroscopic tools were used to characterize the isolated compounds, and their formation mechanisms were discussed. All synthesized compounds were evaluated for their in <em>vitro</em> cytotoxicity against A549, MDA-MB-231 and HeLa cell lines. Compounds <strong>10</strong> and <strong>11</strong> exhibited the most potent cytotoxicity, in comparison with doxorubicin. Furthermore, these two compounds significantly induced early apoptosis and reducing cell viability in the studied tumor cells. Additionally, both compounds <strong>10</strong> and <strong>11</strong> demonstrated promising ability to arrest the cell cycle at the S and G2 phases. In <em>silico</em> ADMET predictions indicated that compounds <strong>10</strong> and <strong>11</strong> possess higher predicted human intestinal absorption (∼89.6% vs. 51.85% for doxorubicin), absence of AMES mutagenicity, and lower predicted acute and chronic oral toxicities in rats. Potential hepatotoxicity and CYP enzyme inhibition were also observed. Molecular docking against EGFR-T790M/V948R revealed that both compound <strong>10</strong> and <strong>11</strong> exhibited a binding affinity of −8.4 and 8.9 kcal/mol, respectively. The interactions of both compounds with key amino acid residues (e.g., LEU 718, VAL 726, ALA 743, MET 790, ASP 855) were consistent with their strong in <em>vitro</em> cytotoxic activity against A549 (EGFR-mutated) cells, supporting their potential as EGFR-targeted anticancer agents.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1413-1435"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
In the current scenario, the use of nature-friendly methods in organic synthesis is regarded as invaluable and irreplaceable. Significant progress has been made in developing more sustainable and eco-friendly approaches for various organic syntheses and transformations. Within the scope of green synthesis, ILs have attracted a lot of interest since their special features fit for sustainable chemistry. Organic synthesis has increasingly utilized ILs as green catalysts and solvents for the development of countless heterocycles. Among these, imidazole is recognized as a highly valuable and preferred heterocyclic motif. It presents interesting chances for finding ideal structures in the synthesis of synthetic compounds with possible therapeutic uses and other major prospects. A diverse array of ILs has been successfully exploited toward the development of imidazoles. Therefore, this review article offers a thorough review of current studies on the function of ecologically safe ILs in producing a wide range of valuable imidazoles.
{"title":"IL-assisted strategy for imidazole: A green recipe","authors":"Vaishali (Writing – original draft) , Shubham Sharma (Supervision Writing – review & editing) , Vinod (Conceptualization Investigation Methodology) , Swati Rani (Software Validation Visualization) , Man Vir Singh (Investigation Validation) , Sodeeq Aderotimi Salami (Validation Visualization) , Sobhi M. Gomha (Project administration Supervision)","doi":"10.1080/00397911.2025.2521832","DOIUrl":"10.1080/00397911.2025.2521832","url":null,"abstract":"<div><div>In the current scenario, the use of nature-friendly methods in organic synthesis is regarded as invaluable and irreplaceable. Significant progress has been made in developing more sustainable and eco-friendly approaches for various organic syntheses and transformations. Within the scope of green synthesis, ILs have attracted a lot of interest since their special features fit for sustainable chemistry. Organic synthesis has increasingly utilized ILs as green catalysts and solvents for the development of countless heterocycles. Among these, imidazole is recognized as a highly valuable and preferred heterocyclic motif. It presents interesting chances for finding ideal structures in the synthesis of synthetic compounds with possible therapeutic uses and other major prospects. A diverse array of ILs has been successfully exploited toward the development of imidazoles. Therefore, this review article offers a thorough review of current studies on the function of ecologically safe ILs in producing a wide range of valuable imidazoles.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1351-1389"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108728","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-17Epub Date: 2025-08-29DOI: 10.1080/00397911.2025.2550435
Chuang Liu (Writing – original draft Writing – review & editing) , Yang Zhou (Formal analysis Supervision) , Wenqiang Pei (Data curation Investigation) , Jinjun Hou (Formal analysis Supervision Validation) , Huali Long (Data curation Supervision) , Zijia Zhang (Conceptualization Supervision Validation) , Qinhua Chen (Funding acquisition Resources) , Yang Yang (Funding acquisition Investigation Resources) , Min Lei (Conceptualization Methodology Supervision Writing – original draft) , Wanying Wu (Funding acquisition Project administration Resources Supervision)
A green and efficient method for synthesizing imidazolidin-4-one derivatives catalyzed by thiamin hydrochloride (VB1) has been developed. This protocol involves the reaction of α-amino amides with carbonyl compounds (aldehydes or ketones) in the presence of VB1 (5 mol%) in EtOH, affording the target products in 50–85% yields. The reaction demonstrates broad substrate compatibility, accommodating aromatic aldehydes, heteroaromatic aldehydes, alkyl aldehydes, and alkyl ketones. Notably, estrone as a ketone substrate successfully undergoes condensation, yielding the corresponding product in 72% yield. The VB1 catalyst offers advantages such as short reaction times, high efficiency, excellent environmental friendliness, and recyclability, maintaining performance over at least three cycles.
{"title":"Thiamin hydrochloride (VB1): A green and efficient catalyst for the synthesis of imidazolidin-4-ones","authors":"Chuang Liu (Writing – original draft Writing – review & editing) , Yang Zhou (Formal analysis Supervision) , Wenqiang Pei (Data curation Investigation) , Jinjun Hou (Formal analysis Supervision Validation) , Huali Long (Data curation Supervision) , Zijia Zhang (Conceptualization Supervision Validation) , Qinhua Chen (Funding acquisition Resources) , Yang Yang (Funding acquisition Investigation Resources) , Min Lei (Conceptualization Methodology Supervision Writing – original draft) , Wanying Wu (Funding acquisition Project administration Resources Supervision)","doi":"10.1080/00397911.2025.2550435","DOIUrl":"10.1080/00397911.2025.2550435","url":null,"abstract":"<div><div>A green and efficient method for synthesizing imidazolidin-4-one derivatives catalyzed by thiamin hydrochloride (VB<sub>1</sub>) has been developed. This protocol involves the reaction of α-amino amides with carbonyl compounds (aldehydes or ketones) in the presence of VB<sub>1</sub> (5 mol%) in EtOH, affording the target products in 50–85% yields. The reaction demonstrates broad substrate compatibility, accommodating aromatic aldehydes, heteroaromatic aldehydes, alkyl aldehydes, and alkyl ketones. Notably, estrone as a ketone substrate successfully undergoes condensation, yielding the corresponding product in 72% yield. The VB<sub>1</sub> catalyst offers advantages such as short reaction times, high efficiency, excellent environmental friendliness, and recyclability, maintaining performance over at least three cycles.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1390-1401"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108729","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A new method for the synthesis of various pyrrole-3-carboximidamide (imidate) derivatives from the multicomponent reaction of alkynes, trichloroacetamide (imidate), and nitro compounds-trichloroacetonitrile adducts under ultrasound (US) irradiation has been reported. The reaction of nitromethane (or ethane) with trichloroacetonitrile in the presence of sodium hydride as a base led to the formation of nitro compounds-trichloroacetonitrile adducts, which subsequently led to the synthesis of new pyrrole-3-carboxyimidamide (imidate) derivatives in good yields by the addition of alkynes and trichloroacetamide (imidate). The use of an inexpensive copper (I) catalyst, under ultrasonic conditions as an energy source for 50 min, in the absence of ligands and oxidants, CH2Cl2 solvent, and the synthesis and identification of new compounds are important in this research. The combination of mild reaction conditions, one-pot, five-component, catalytic systems, available starting materials, and ease of purification methods facilitates the synthesis of diverse new substituted pyrroles, including amidine and imidate skeletons.
{"title":"Innovative ultrasound‐assisted synthesis of new highly functionalized pyrroles derivatives from alkynes, trichloroacet-amidine(imidate), and nitro compounds-trichloroacetonitrile adducts","authors":"Manijeh Nematpour (Data curation Formal analysis Supervision Writing – review & editing)","doi":"10.1080/00397911.2025.2558717","DOIUrl":"10.1080/00397911.2025.2558717","url":null,"abstract":"<div><div>A new method for the synthesis of various pyrrole-3-carboximidamide (imidate) derivatives from the multicomponent reaction of alkynes, trichloroacetamide (imidate), and nitro compounds-trichloroacetonitrile adducts under ultrasound (US) irradiation has been reported. The reaction of nitromethane (or ethane) with trichloroacetonitrile in the presence of sodium hydride as a base led to the formation of nitro compounds-trichloroacetonitrile adducts, which subsequently led to the synthesis of new pyrrole-3-carboxyimidamide (imidate) derivatives in good yields by the addition of alkynes and trichloroacetamide (imidate). The use of an inexpensive copper (I) catalyst, under ultrasonic conditions as an energy source for 50 min, in the absence of ligands and oxidants, CH<sub>2</sub>Cl<sub>2</sub> solvent, and the synthesis and identification of new compounds are important in this research. The combination of mild reaction conditions, one-pot, five-component, catalytic systems, available starting materials, and ease of purification methods facilitates the synthesis of diverse new substituted pyrroles, including amidine and imidate skeletons.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 18","pages":"Pages 1402-1412"},"PeriodicalIF":1.8,"publicationDate":"2025-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145108724","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-02Epub Date: 2025-08-21DOI: 10.1080/00397911.2025.2548301
Yawen Hu (Conceptualization Data curation Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Li Xu (Data curation Formal analysis) , Xue Jiang (Data curation Supervision) , Haiyang Guo (Formal analysis Investigation) , Di Wu (Conceptualization Data curation Methodology Writing – review & editing)
A recyclable ligand chitosan was developed for the copper-catalyzed Ullmann-type cross-coupling reaction of aryl halides with amines. A variety of functionalized (hetero)aryl halides reacted smoothly with pyrazole, imidazole, aliphatic amines and ammonia to provide a wide range of (hetero)aryl amines in good to excellent yields under the catalyst of Cu2O/chitosan system. This method has the advantages of wide substrate range, high chemoselectivity, and good functional group compatibility. The ligand is easily recycled and no significant decrease in the catalytic potency after being reused 7 times.
{"title":"Recyclable chitosan for copper-catalyzed Ullmann C-N coupling reaction","authors":"Yawen Hu (Conceptualization Data curation Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Li Xu (Data curation Formal analysis) , Xue Jiang (Data curation Supervision) , Haiyang Guo (Formal analysis Investigation) , Di Wu (Conceptualization Data curation Methodology Writing – review & editing)","doi":"10.1080/00397911.2025.2548301","DOIUrl":"10.1080/00397911.2025.2548301","url":null,"abstract":"<div><div>A recyclable ligand chitosan was developed for the copper-catalyzed Ullmann-type cross-coupling reaction of aryl halides with amines. A variety of functionalized (hetero)aryl halides reacted smoothly with pyrazole, imidazole, aliphatic amines and ammonia to provide a wide range of (hetero)aryl amines in good to excellent yields under the catalyst of Cu<sub>2</sub>O/chitosan system. This method has the advantages of wide substrate range, high chemoselectivity, and good functional group compatibility. The ligand is easily recycled and no significant decrease in the catalytic potency after being reused 7 times.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 17","pages":"Pages 1340-1350"},"PeriodicalIF":1.8,"publicationDate":"2025-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145048723","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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