Eco-friendly construction of a 3-(3,5-bis(trifluoromethyl)phenyl)-1-((5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridin-2(1H)-one derivatives (10a–j) under microwave method furnished excellent yields in minimal time with maximum selectivity in the presence of PhI(OAc)2. This route aligns with the principles of green chemistry due to its significantly reduced reaction time and enriched energy efficiency, simplicity, and high yields. The synthesized compounds were characterized by spectroscopic techniques IR,1H NMR,13C NMR, Mass spectrometry, and elemental analysis studies. All the synthesized compounds cytotoxicity was tested against four cancer cell lines, MCF-7, Colo-205, A549, and SiHa human Cervix cancer cell lines; all the compounds demonstrated remarkable in vitro anticancer activity, notably, among them, compound 10i exhibited the most potent anti-cancer activity of IC50 valves are 11.21 ± 0.17 μM (MCF-7 breast cancer cell line), 11.62 ± 0.54 μM (Colo-205 colon cancer cell line), 17.85 ± 0.48 μM (A549 lung carcinoma epithelial cells), 19.64 ± 0.46 μM (SiHa human Cervix cancer cell line) compared with clinical standard drug.
{"title":"Green synthesis and anticancer evaluation of novel bis-(trifluoromethyl-5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridine scaffolds","authors":"Mahesh Ellanti (Conceptualization Data curation Validation Writing – review & editing) , Divya A (Software) , Kavati Shireesha (Visualization) , Kumara Swamy Jella (Supervision)","doi":"10.1080/00397911.2025.2501211","DOIUrl":"10.1080/00397911.2025.2501211","url":null,"abstract":"<div><div>Eco-friendly construction of a 3-(3,5-bis(trifluoromethyl)phenyl)-1-((5-phenyl-1,3,4-oxadiazol-2-yl) methyl)-1,8-naphthyridin-2(1H)-one derivatives (<strong>10a–j</strong>) under microwave method furnished excellent yields in minimal time with maximum selectivity in the presence of PhI(OAc)<sub>2</sub>. This route aligns with the principles of green chemistry due to its significantly reduced reaction time and enriched energy efficiency, simplicity, and high yields. The synthesized compounds were characterized by spectroscopic techniques IR,<sup>1</sup>H NMR,<sup>13</sup>C NMR, Mass spectrometry, and elemental analysis studies. All the synthesized compounds cytotoxicity was tested against four cancer cell lines, MCF-7, Colo-205, A549, and SiHa human Cervix cancer cell lines; all the compounds demonstrated remarkable <em>in vitro</em> anticancer activity, notably, among them, compound 10i exhibited the most potent anti-cancer activity of IC<sub>50</sub> valves are 11.21 ± 0.17 μM (MCF-7 breast cancer cell line), 11.62 ± 0.54 μM (Colo-205 colon cancer cell line), 17.85 ± 0.48 μM (A549 lung carcinoma epithelial cells), 19.64 ± 0.46 μM (SiHa human Cervix cancer cell line) compared with clinical standard drug.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 815-824"},"PeriodicalIF":1.8,"publicationDate":"2025-05-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124340","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 : 2025-05-07DOI: 10.1080/00397911.2025.2500720
Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) , Ankur G Pandey (Writing – review & editing)
Catalysts play an integral role in rationalizing several organic reactions despite suffering major challenges like poor efficiency, high cost and toxicity. In this work, we have reported a green, cost effective and highly efficient squaric acid as an organocatalyst for catalyzing two of the most vital organic reactions, Knoevenagel condensation and 1,6-conjugate addition reactions. Under our optimized conditions, the organocatayst showed excellent yields of up to 94% for both the reactions with an extensive substrate scope and excellent reusability for multiple reaction cycles. In addition, the catalytic efficacy of squaric acid was showcased by employing it in the synthesis of 2-amino-4H-chromene derivatives.
{"title":"Squaric acid as an organocatalyst for Knoevenagel condensation and 1,6-conjugate addition reactions","authors":"Nirmal Singh (Conceptualization Formal analysis Methodology Writing – original draft) , Ankur G Pandey (Writing – review & editing)","doi":"10.1080/00397911.2025.2500720","DOIUrl":"10.1080/00397911.2025.2500720","url":null,"abstract":"<div><div>Catalysts play an integral role in rationalizing several organic reactions despite suffering major challenges like poor efficiency, high cost and toxicity. In this work, we have reported a green, cost effective and highly efficient squaric acid as an organocatalyst for catalyzing two of the most vital organic reactions, Knoevenagel condensation and 1,6-conjugate addition reactions. Under our optimized conditions, the organocatayst showed excellent yields of up to 94% for both the reactions with an extensive substrate scope and excellent reusability for multiple reaction cycles. In addition, the catalytic efficacy of squaric acid was showcased by employing it in the synthesis of 2-amino-<em>4H</em>-chromene derivatives.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 11","pages":"Pages 804-814"},"PeriodicalIF":1.8,"publicationDate":"2025-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144124369","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 : 2025-05-05DOI: 10.1080/00397911.2025.2500050
Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)
A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and o-aminobenzamides in the presence of DTBP/Cu(OTf)2 has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3H)-one (3a) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.
{"title":"DTBP mediated tandem oxidative reaction of o-aminobenzamides with alcohols for the synthesis of quinazolinones","authors":"Jin Li (Investigation Writing – original draft) , Haotian Cao (Investigation Methodology) , Hongyou Tian (Data curation Investigation) , Huaju Li (Data curation) , Yongke Hu (Funding acquisition Project administration Writing – review & editing)","doi":"10.1080/00397911.2025.2500050","DOIUrl":"10.1080/00397911.2025.2500050","url":null,"abstract":"<div><div>A practical and efficient methodology for the construction of quinazolinones from readily available alcohols and <em>o</em>-aminobenzamides in the presence of DTBP/Cu(OTf)<sub>2</sub> has been developed. This catalytic system exhibits good functional group tolerance and could afford a range of quinazolinones in good to excellent yields. In case of gram-scale reaction, 2-phenylquinazolin-4(3<em>H</em>)-one (<strong>3a</strong>) was obtained in 86% isolated yield, which indicated this protocol was amenable to scale up and had a potential value in industry. In addition, a plausible reaction mechanism involving a radical process has been proposed, and further applications of this catalytic system are under way in our laboratory.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 774-782"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948411","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 simple and efficient ligand-assisted iron-catalyzed system for the C-N coupling of 7-azaindole with aryl iodides was developed using water as the sole solvent. Under the optimum conditions, the N-arylated products were obtained in good yields up to 96%.
{"title":"Iron catalyzed N-arylation of 7-azaindole with aryl iodides","authors":"Yong-Chua Teo (Conceptualization Funding acquisition Supervision Writing – original draft Writing – review & editing) , Ying-Rui Tan (Investigation Methodology) , Wei-Zhi Ang (Investigation Methodology) , Anthia Shun-Ai Teo (Investigation Methodology)","doi":"10.1080/00397911.2025.2496968","DOIUrl":"10.1080/00397911.2025.2496968","url":null,"abstract":"<div><div>A simple and efficient ligand-assisted iron-catalyzed system for the C-N coupling of 7-azaindole with aryl iodides was developed using water as the sole solvent. Under the optimum conditions, the N-arylated products were obtained in good yields up to 96%.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 739-748"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948427","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}
Tuberculosis (TB) remains a significant global health challenge, with 10 million new cases and 1 million deaths annually. The limited availability of anti-TB drugs, prolonged treatment regimens, and drug resistance underscores the urgent need for new therapeutic agents. Leveraging the pharmacological potential of benzimidazole and thiazolylhydrazone scaffolds, we designed and synthesized a series of novel benzimidazole-thiazolylhydrazone derivatives. These compounds were prepared via reactions of phenacyl bromides with thiosemicarbazide and benzimidazole-containing arylaldehydes in ethanol with catalytic acetic acid. In vitro testing against Mycobacterium tuberculosis (H37Rv) revealed notable activity for 4-fluorophenyl (4b) and 4-bromophenyl (4d) derivatives, with MIC values of 3.125 μg/mL and 6.25 μg/mL, respectively. Molecular docking suggested compound 4b targets DprE1, crucial in mycobacterial cell wall synthesis, with a binding energy of −10.9 kcal/mol. In silico ADME analysis confirmed drug-likeness, and TOPKAT studies indicated non-carcinogenicity. These results position compound 4b as a promising lead for further TB drug development.
{"title":"Design, synthesis and antimycobacterial evaluation of benzimidazole-thiazolylhydrazone derivatives: In silico molecular docking studies, DFT analysis and ADMET predictions","authors":"Arya C. G. (Data curation Formal analysis Methodology Writing – original draft) , Jyothi Kumari (Data curation Formal analysis) , Siddhardha Busi (Data curation Formal analysis Investigation Writing – review & editing) , Simi Asma Salim (Data curation Formal analysis) , Munugala Chandrakanth (Data curation Formal analysis Software) , Dharmarajan Sriram (Data curation Formal analysis Investigation Writing – review & editing) , Ramesh Gondru (Data curation Formal analysis Software Visualization Writing – review & editing) , Janardhan Banothu (Conceptualization Funding acquisition Investigation Project administration Resources Supervision Validation Visualization Writing – review & editing)","doi":"10.1080/00397911.2025.2498535","DOIUrl":"10.1080/00397911.2025.2498535","url":null,"abstract":"<div><div>Tuberculosis (TB) remains a significant global health challenge, with 10 million new cases and 1 million deaths annually. The limited availability of anti-TB drugs, prolonged treatment regimens, and drug resistance underscores the urgent need for new therapeutic agents. Leveraging the pharmacological potential of benzimidazole and thiazolylhydrazone scaffolds, we designed and synthesized a series of novel benzimidazole-thiazolylhydrazone derivatives. These compounds were prepared <em>via</em> reactions of phenacyl bromides with thiosemicarbazide and benzimidazole-containing arylaldehydes in ethanol with catalytic acetic acid. <em>In vitro</em> testing against <em>Mycobacterium tuberculosis</em> (H37Rv) revealed notable activity for 4-fluorophenyl (<strong>4b</strong>) and 4-bromophenyl (<strong>4d</strong>) derivatives, with MIC values of 3.125 μg/mL and 6.25 μg/mL, respectively. Molecular docking suggested compound <strong>4b</strong> targets DprE1, crucial in mycobacterial cell wall synthesis, with a binding energy of −10.9 kcal/mol. <em>In silico</em> ADME analysis confirmed drug-likeness, and TOPKAT studies indicated non-carcinogenicity. These results position compound <strong>4b</strong> as a promising lead for further TB drug development.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 10","pages":"Pages 758-773"},"PeriodicalIF":1.8,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143948410","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 : 2025-05-03DOI: 10.1080/00397911.2025.2454961
Sunita Yadav , Ankita , Aakash Singh , Ruby Singh
Synthesis of structurally intriguing iminothiazolidinone tethered dispiropyrrolizidine/pyrrolothiazole hybrids have been achieved with complete regio- and diastereoselectivity in excellent yields via a one-pot three component 1,3-dipolar cycloaddition strategy employing alkyl-2-[(Z)-4-oxo-3-aryl/alkyl-2-(arylimino)thiazolidin-5-ylidene] acetates as dipolarophiles and azomethine ylide derived from two cyclic ketones (isatin and acenaphthaquinone) and cyclic amino acids (l-proline and l-thiaproline) using biodegradable deep eutectic solvent. During the entire transformation, three additional bonds are formed with generation of four stereogenic carbons in target molecule in a single step reaction. The synthesized compounds were structurally elucidated using NMR spectroscopic studies, and the regio-and stereoselectivity was determined through single crystal X-ray diffraction study.
{"title":"A sequential multicomponent reaction toward the construction of a novel contiguous imino-thiazolidinone grafted dispiroheterocyclic scaffolds","authors":"Sunita Yadav , Ankita , Aakash Singh , Ruby Singh","doi":"10.1080/00397911.2025.2454961","DOIUrl":"10.1080/00397911.2025.2454961","url":null,"abstract":"<div><div>Synthesis of structurally intriguing iminothiazolidinone tethered dispiropyrrolizidine/pyrrolothiazole hybrids have been achieved with complete regio- and diastereoselectivity in excellent yields <em>via</em> a one-pot three component 1,3-dipolar cycloaddition strategy employing alkyl-2-[(<em>Z</em>)-4-oxo-3-aryl/alkyl-2-(arylimino)thiazolidin-5-ylidene] acetates as dipolarophiles and azomethine ylide derived from two cyclic ketones (isatin and acenaphthaquinone) and cyclic amino acids (<span>l</span>-proline and <span>l</span>-thiaproline) using biodegradable deep eutectic solvent. During the entire transformation, three additional bonds are formed with generation of four stereogenic carbons in target molecule in a single step reaction. The synthesized compounds were structurally elucidated using NMR spectroscopic studies, and the regio-and stereoselectivity was determined through single crystal X-ray diffraction study.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 631-642"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929192","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 : 2025-05-03DOI: 10.1080/00397911.2025.2495140
Swapnil J. Wagh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Baludev D. Dadas (Formal analysis Investigation Writing – original draft Writing – review & editing) , Trupti S. Tawde (Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Sumaiya Shaikh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Anil V. Karnik (Conceptualization Investigation Methodology Project administration Supervision Visualization Writing – original draft Writing – review & editing)
Chiral-pool approach has been invoked in a three-step synthetic protocol for the synthesis of 9-membered Benzimidazole-derived organo-Phosphoric Acid (HEBEN-PA). The HEBEN-PA has two fused aryl rings incorporated in the structure to minimize conformational changes. The HEBEN-PA was successfully employed as a Chiral Bronsted acid catalyst for the enantiomerically enriched dihydroquinazolinone synthesis. Synthesis of dihydroquinazolinone occurred with good yields. Effect of solvent, temperature, and the substituents on the level of enantioselectivity have been examined.
{"title":"Synthesis of benzimidazole-derived chiral cyclic phosphoric acid and its application in asymmetric induction process","authors":"Swapnil J. Wagh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Baludev D. Dadas (Formal analysis Investigation Writing – original draft Writing – review & editing) , Trupti S. Tawde (Formal analysis Investigation Methodology Writing – original draft Writing – review & editing) , Sumaiya Shaikh (Data curation Investigation Methodology Writing – original draft Writing – review & editing) , Anil V. Karnik (Conceptualization Investigation Methodology Project administration Supervision Visualization Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2495140","DOIUrl":"10.1080/00397911.2025.2495140","url":null,"abstract":"<div><div>Chiral-pool approach has been invoked in a three-step synthetic protocol for the synthesis of 9-membered Benzimidazole-derived organo-Phosphoric Acid (HEBEN-PA). The HEBEN-PA has two fused aryl rings incorporated in the structure to minimize conformational changes. The HEBEN-PA was successfully employed as a Chiral Bronsted acid catalyst for the enantiomerically enriched dihydroquinazolinone synthesis. Synthesis of dihydroquinazolinone occurred with good yields. Effect of solvent, temperature, and the substituents on the level of enantioselectivity have been examined.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 643-651"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929193","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 : 2025-05-03DOI: 10.1080/00397911.2025.2494245
Quansen Wu (Methodology Writing – review & editing) , Zizhong Ma (Data curation) , Rui Li (Methodology) , Ruiqiang Shang (Methodology) , Zhenyu An (Writing – original draft) , Yafeng Liu (Writing – original draft) , Qing Huang (Writing – review & editing) , Zhenjie Qi (Conceptualization Funding acquisition Project administration Writing – original draft Writing – review & editing)
A novel method for the synthesis of amides has been developed that features – tert-butyl nitrite-induced oxidative cross-coupling of acetonitrile with N-sulfinylanilines. Acetonitrile serves as the C2 building block in this process. The present protocol effectively inhibits the competition with the C≡N triple bond but enables the in situ formation of unsaturated C–O bond. The reaction demonstrates a broad substrate scope and can be conducted under mild conditions. Mechanistic studies, including radical trapping experiments and H218O-labeling, confirm a radical-mediated pathway involving acetonitrile-derived intermediates. Additionally, this method is amenable to gram-scale synthesis.
{"title":"Synthesis of amides via TBN-induced oxidation cross-coupling of acetonitrile and N-sulfinylanilines","authors":"Quansen Wu (Methodology Writing – review & editing) , Zizhong Ma (Data curation) , Rui Li (Methodology) , Ruiqiang Shang (Methodology) , Zhenyu An (Writing – original draft) , Yafeng Liu (Writing – original draft) , Qing Huang (Writing – review & editing) , Zhenjie Qi (Conceptualization Funding acquisition Project administration Writing – original draft Writing – review & editing)","doi":"10.1080/00397911.2025.2494245","DOIUrl":"10.1080/00397911.2025.2494245","url":null,"abstract":"<div><div>A novel method for the synthesis of amides has been developed that features – <em>tert</em>-butyl nitrite-induced oxidative cross-coupling of acetonitrile with <em>N</em>-sulfinylanilines. Acetonitrile serves as the C2 building block in this process. The present protocol effectively inhibits the competition with the C≡N triple bond but enables the in <em>situ</em> formation of unsaturated C–O bond. The reaction demonstrates a broad substrate scope and can be conducted under mild conditions. Mechanistic studies, including radical trapping experiments and H<sub>2</sub><sup>18</sup>O-labeling, confirm a radical-mediated pathway involving acetonitrile-derived intermediates. Additionally, this method is amenable to gram-scale synthesis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 652-660"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929191","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 : 2025-05-03DOI: 10.1080/00397911.2025.2495139
Parusharamudu K (Investigation Methodology) , Bhanu Prasad Banda (Investigation Methodology) , Krishnaiah Atmakur (Conceptualization Methodology Supervision Validation Writing – original draft)
Synthesis of polysubstituted 2-methylene-1,2-dihydropyridines were accomplished by one-pot multicomponent reaction of 3-formylchromones, anilines and aliphatic 1,3-diones under catalyst and solvent-free reaction conditions. The reaction proceeds via Schiff base mediated, Michael addition followed by ring opening/ring closure sequential process resulting two new C–N and one C–C bonds formation. Neat reaction conditions and higher yields are the advantages of the protocol.
{"title":"A catalyst and solvent free synthesis of polysubstituted 2-methylene-1,2-dihydropyridines","authors":"Parusharamudu K (Investigation Methodology) , Bhanu Prasad Banda (Investigation Methodology) , Krishnaiah Atmakur (Conceptualization Methodology Supervision Validation Writing – original draft)","doi":"10.1080/00397911.2025.2495139","DOIUrl":"10.1080/00397911.2025.2495139","url":null,"abstract":"<div><div>Synthesis of polysubstituted 2-methylene-1,2-dihydropyridines were accomplished by one-pot multicomponent reaction of 3-formylchromones, anilines and aliphatic 1,3-diones under catalyst and solvent-free reaction conditions. The reaction proceeds <em>via</em> Schiff base mediated, Michael addition followed by ring opening/ring closure sequential process resulting two new C–N and one C–C bonds formation. Neat reaction conditions and higher yields are the advantages of the protocol.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 683-691"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929189","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 : 2025-05-03DOI: 10.1080/00397911.2025.2493953
Guojie Yin (Investigation Writing – original draft) , Canli Zhang (Investigation) , Qiong Liu (Data curation Writing – review & editing) , Youju Shu (Data curation) , Weijun Fu (Conceptualization Supervision Writing – original draft)
An efficient monofluoromethylation of N-acryl-2-aryl benzimidazoles was developed through an electro-oxidative CFH2-radical generation, followed by cascade cyclization fabricating a benzimidazo[2,1-a]isoquinolin-6(5H)-one scaffold. The protocol used the readily available CFH2SO2Na as the monofluoromethylation reagent, enabling the step economical synthesis of polycyclic benzimidazoles in moderate to high yields under metal- and oxidant-free conditions. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that the necessity of anodic oxidation in the cascade process.
{"title":"Electrochemical oxidative monofluoromethylation of N-acryl-2-aryl benzimidazoles: access to CFH2-containing benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives","authors":"Guojie Yin (Investigation Writing – original draft) , Canli Zhang (Investigation) , Qiong Liu (Data curation Writing – review & editing) , Youju Shu (Data curation) , Weijun Fu (Conceptualization Supervision Writing – original draft)","doi":"10.1080/00397911.2025.2493953","DOIUrl":"10.1080/00397911.2025.2493953","url":null,"abstract":"<div><div>An efficient monofluoromethylation of N-acryl-2-aryl benzimidazoles was developed through an electro-oxidative CFH<sub>2</sub>-radical generation, followed by cascade cyclization fabricating a benzimidazo[2,1-a]isoquinolin-6(5H)-one scaffold. The protocol used the readily available CFH<sub>2</sub>SO<sub>2</sub>Na as the monofluoromethylation reagent, enabling the step economical synthesis of polycyclic benzimidazoles in moderate to high yields under metal- and oxidant-free conditions. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that the necessity of anodic oxidation in the cascade process.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 9","pages":"Pages 661-671"},"PeriodicalIF":1.8,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143929188","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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