A series of spirocyclic pyrrolidine derivatives with quaternary stereocenters was constructed via asymmetric [3 + 2] cycloaddition reactions between imino esters and 2-oxindole. By ingenious use of ligands on the silver catalyst allows stereoselectivity to either endo-isomers (ee up to 98 %, yields up to 96 %) with (R, Rp)-Ph-Phosferrox or exo-isomers (ee up to 99 %, yields up to 87 %) with (R)-BINAP. This work is notable for its high yields, broad substrate adaptability and excellent enantioselectivity.
{"title":"Diastereoselective Stereo-Divergent Synthesis of Spiroindolines via Ligand-Controlled Silver(I)-Catalyzed Asymmetric [3 + 2] cycloadditions","authors":"Yangmin Ma, Xuemei Zhang, Gege Dang, Miao Xia, Zhaoyang Sun, Siyue Ma, Wenting Zhang","doi":"10.1016/j.tet.2024.134291","DOIUrl":"10.1016/j.tet.2024.134291","url":null,"abstract":"<div><div>A series of spirocyclic pyrrolidine derivatives with quaternary stereocenters was constructed via asymmetric [3 + 2] cycloaddition reactions between imino esters and 2-oxindole. By ingenious use of ligands on the silver catalyst allows stereoselectivity to either <em>endo</em>-isomers (ee up to 98 %, yields up to 96 %) with (<em>R</em>, <em>Rp</em>)-Ph-Phosferrox or <em>exo</em>-isomers (ee up to 99 %, yields up to 87 %) with (<em>R</em>)-BINAP. This work is notable for its high yields, broad substrate adaptability and excellent enantioselectivity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134291"},"PeriodicalIF":2.1,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425575","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 : 2024-10-03DOI: 10.1016/j.tet.2024.134289
Tina Abbasi , Mohammad Bagher Teimouri , Issa Yavari , Rahman Bikas , Tadeusz Lis
A green one-pot reaction involving cyclic secondary amines, activated alkynes, and alloxan derivatives in water has been established, offering a cost-effective and selective route to (enamino)hydroxybarbiturates and 3-amino-5-hydroxycyclopent-2-enone-derived carbonylureas with high yields. This method utilizes readily available starting materials to produce valuable compounds for medicinal chemistry and organic synthesis through a three-component cascade reaction under mild conditions.
{"title":"Regioselective synthesis of functionalized cyclopent-2-enone-derived carbonylureas and enaminohydroxybarbiturates from alloxans in water","authors":"Tina Abbasi , Mohammad Bagher Teimouri , Issa Yavari , Rahman Bikas , Tadeusz Lis","doi":"10.1016/j.tet.2024.134289","DOIUrl":"10.1016/j.tet.2024.134289","url":null,"abstract":"<div><div>A green one-pot reaction involving cyclic secondary amines, activated alkynes, and alloxan derivatives in water has been established, offering a cost-effective and selective route to (enamino)hydroxybarbiturates and 3-amino-5-hydroxycyclopent-2-enone-derived carbonylureas with high yields. This method utilizes readily available starting materials to produce valuable compounds for medicinal chemistry and organic synthesis through a three-component cascade reaction under mild conditions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134289"},"PeriodicalIF":2.1,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425569","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 : 2024-10-03DOI: 10.1016/j.tet.2024.134290
Rachana Upadhyay, Amit B. Patel
Herein, a novel approach of bimetallic Pd(OAc)2/CuI-catalyzed alkynylation of 3-chloroazetidin-2-one (β-lactam derivative) with terminal alkyne via tandem C–C bond activation/Sonogashira-type cross-coupling reaction is developed. This synthesis encompasses a sequence of inert Csp3–X/Csp–H functionalization processes involving the coupling of the C(sp3) adjacent to the 3-chloroazetidin-2-one with the C(sp) of a terminal alkyne. The final analogs are synthesized by means of the indole-benzothiazole Schiff base formation, cyclization of the Schiff base to generate the β-lactam derivative, and Sonogashira coupling to afford a C(sp3)–C(sp) bond. In addition, indole, benzothiazole, and azetidine-2-one have been identified to be highly efficient heterocyclic scaffolds with a range of pharmacological benefits. It encouraged us to discover a hybrid compound that had each of these moieties. Cooperation between two different metals is essential for the successful implementation of this approach. Specifically, the interaction between the Pd and Cu centers in the transmetallation step is depicted through a plausible mechanistic route. The reaction conditions have been optimized by varying catalyst and ligand loadings, bases, temperatures, and solvents. The reaction is highly efficient, yielding alkynylated products in up to 84 % yield with a wide range of substrates and functional group tolerance, thereby serving as a functional model for the Sonogashira coupling reaction.
{"title":"Synergistic Pd(OAc)2/CuI-catalyzed alkynylation of β-lactam derivative via Sonogashira coupling","authors":"Rachana Upadhyay, Amit B. Patel","doi":"10.1016/j.tet.2024.134290","DOIUrl":"10.1016/j.tet.2024.134290","url":null,"abstract":"<div><div>Herein, a novel approach of bimetallic Pd(OAc)<sub>2</sub>/CuI-catalyzed alkynylation of 3-chloroazetidin-2-one (<em>β</em>-lactam derivative) with terminal alkyne <em>via</em> tandem C–C bond activation/Sonogashira-type cross-coupling reaction is developed. This synthesis encompasses a sequence of inert Csp<sup>3</sup>–X/Csp–H functionalization processes involving the coupling of the C(sp<sup>3</sup>) adjacent to the 3-chloroazetidin-2-one with the C(sp) of a terminal alkyne. The final analogs are synthesized by means of the indole-benzothiazole Schiff base formation, cyclization of the Schiff base to generate the <em>β</em>-lactam derivative, and Sonogashira coupling to afford a C(sp<sup>3</sup>)–C(sp) bond. In addition, indole, benzothiazole, and azetidine-2-one have been identified to be highly efficient heterocyclic scaffolds with a range of pharmacological benefits. It encouraged us to discover a hybrid compound that had each of these moieties. Cooperation between two different metals is essential for the successful implementation of this approach. Specifically, the interaction between the Pd and Cu centers in the transmetallation step is depicted through a plausible mechanistic route. The reaction conditions have been optimized by varying catalyst and ligand loadings, bases, temperatures, and solvents. The reaction is highly efficient, yielding alkynylated products in up to 84 % yield with a wide range of substrates and functional group tolerance, thereby serving as a functional model for the Sonogashira coupling reaction.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134290"},"PeriodicalIF":2.1,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425566","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 : 2024-10-02DOI: 10.1016/j.tet.2024.134288
Mao-Juan Tian, Hua-Qing Tian, Tao Jiang, Huan-Huan Yu, Chao Huang, Bi-Xue Zhu, Chun Zhu
A racemic salicylaldehyde Schiff base (L) containing a pyridine-2,6-dicarboxamide scaffold was successfully synthesized and characterized. L exhibited a typical aggregation-induced emission (AIE) characteristic in the mixed solvent of THF/H2O. The UV–Vis absorption spectra and fluorescence emission spectra showed a high selectivity and sensitivity of L for the recognition of Cu2+ over other ions in the solution of THF/H2O (2:3), and indicated L can be used as a turn-off fluorescent probe for Cu2+. The stoichiometric ratio, association constant, and the detection limit of probe L toward Cu2+ were estimated using Job's plot method, UV–Vis spectra titration, and fluorescence spectra titration. More importantly, a Cu(II) complex was synthesized from the coordination interaction of probe L with Cu2+ and characterized by X-ray crystal diffraction technique. The crystal structure well illustrated the binding mode of L with Cu2+, contributing to the further understanding of the coordination mechanism.
成功合成并表征了一种含有吡啶-2,6-二甲酰胺支架的外消旋水杨醛席夫碱（L）。在 THF/H2O 混合溶剂中，L 表现出典型的聚集诱导发射（AIE）特征。紫外可见吸收光谱和荧光发射光谱显示，在 THF/H2O 溶液（2:3）中，L 对 Cu2+ 的识别具有较高的选择性和灵敏度，表明 L 可用作 Cu2+ 的熄灭荧光探针。利用约伯图法、紫外可见光谱滴定法和荧光光谱滴定法估算了探针 L 对 Cu2+ 的化学计量比、关联常数和检测限。更重要的是，利用探针 L 与 Cu2+ 的配位相互作用合成了一种 Cu（II）配合物，并利用 X 射线晶体衍射技术对其进行了表征。晶体结构很好地展示了 L 与 Cu2+ 的结合模式，有助于进一步了解配位机理。
{"title":"A helical salicylaldehyde Schiff base exhibiting aggregation-induced emission and selective recognition of Cu2+ ions","authors":"Mao-Juan Tian, Hua-Qing Tian, Tao Jiang, Huan-Huan Yu, Chao Huang, Bi-Xue Zhu, Chun Zhu","doi":"10.1016/j.tet.2024.134288","DOIUrl":"10.1016/j.tet.2024.134288","url":null,"abstract":"<div><div>A racemic salicylaldehyde Schiff base (<strong>L</strong>) containing a pyridine-2,6-dicarboxamide scaffold was successfully synthesized and characterized. <strong>L</strong> exhibited a typical aggregation-induced emission (AIE) characteristic in the mixed solvent of THF/H<sub>2</sub>O. The UV–Vis absorption spectra and fluorescence emission spectra showed a high selectivity and sensitivity of <strong>L</strong> for the recognition of Cu<sup>2+</sup> over other ions in the solution of THF/H<sub>2</sub>O (2:3), and indicated <strong>L</strong> can be used as a turn-off fluorescent probe for Cu<sup>2+</sup>. The stoichiometric ratio, association constant, and the detection limit of probe <strong>L</strong> toward Cu<sup>2+</sup> were estimated using Job's plot method, UV–Vis spectra titration, and fluorescence spectra titration. More importantly, a Cu(II) complex was synthesized from the coordination interaction of probe <strong>L</strong> with Cu<sup>2+</sup> and characterized by X-ray crystal diffraction technique. The crystal structure well illustrated the binding mode of <strong>L</strong> with Cu<sup>2+</sup>, contributing to the further understanding of the coordination mechanism.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134288"},"PeriodicalIF":2.1,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425568","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 : 2024-09-30DOI: 10.1016/j.tet.2024.134287
Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai
An I2-promoted C–H arylselenylation of pyrrolo[1,2-a]quinoxalines with diaryl diselenides is developed, providing an efficient route to a series of 1 (or 3)-arylselenylated and/or 1,3-diaryl diselenylated pyrrolo[1,2-a]quinoxalines. The methodology is characterised by a wide range of substrates, good functional group tolerance and gram-level synthesis. Further transformations of the products to form structurally diverse pyrrolo[1,2-a]quinoxalines were successfully achieved. Similarly, I2-promoted C–H sulfenylation of pyrrolo[1,2-a]quinoxaline with 1,2-diphenyldisulfane were investigated. We believe that these novel pyrrolo[1,2-a]quinoxaline compounds will have promising applications in pharmaceutical synthesis.
{"title":"I2-promoted direct C–H arylselenylation of pyrrolo[1,2-a]quinoxalines","authors":"Di Hao , Zhen Yang , Luigi Vaccaro , Ping Liu , Bin Dai","doi":"10.1016/j.tet.2024.134287","DOIUrl":"10.1016/j.tet.2024.134287","url":null,"abstract":"<div><div>An I<sub>2</sub>-promoted C–H arylselenylation of pyrrolo[1,2-<em>a</em>]quinoxalines with diaryl diselenides is developed, providing an efficient route to a series of 1 (or 3)-arylselenylated and/or 1,3-diaryl diselenylated pyrrolo[1,2-<em>a</em>]quinoxalines. The methodology is characterised by a wide range of substrates, good functional group tolerance and gram-level synthesis. Further transformations of the products to form structurally diverse pyrrolo[1,2-<em>a</em>]quinoxalines were successfully achieved. Similarly, I<sub>2</sub>-promoted C–H sulfenylation of pyrrolo[1,2-<em>a</em>]quinoxaline with 1,2-diphenyldisulfane were investigated. We believe that these novel pyrrolo[1,2-<em>a</em>]quinoxaline compounds will have promising applications in pharmaceutical synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134287"},"PeriodicalIF":2.1,"publicationDate":"2024-09-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425565","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}
We present an efficient, acid-mediated cascade strategy for the construction of 1,3- and 1,2,3-substituted naphthalenes from readily accessible starting materials. This method employs ortho-alkynyl or arynyl tertiary benzylic alcohols as the substrates, which undergo a Lewis acid-triggered dehydration to form ortho-(alkynyl)-styrene intermediates. These intermediates subsequently undergo intramolecular cycloaromatization, resulting in the formation of substituted naphthalenes in a one-pot reaction. A significant advantage of this approach is its ability to proceed under sustainable and neat reaction conditions using ZnCl₂ as the sole Lewis acid, highlighting the simplicity and practicality of the process. Additionally, the strategy exhibits a broad substrate scope, efficiently yielding the desired naphthalene derivatives with practical and consistent yields. This method not only simplifies the synthetic pathway but also aligns with green chemistry principles by minimizing the use of solvents and reagents.
{"title":"An acid-mediated synthesis of substituted naphthalenes from ortho-alkynyl tertiary benzylic alcohols","authors":"Puja Singh, Sreenivasulu Chinnabattigalla, Komal Goel, Ravi Kishore Dakoju, Satyanarayana Gedu","doi":"10.1016/j.tet.2024.134285","DOIUrl":"10.1016/j.tet.2024.134285","url":null,"abstract":"<div><div>We present an efficient, acid-mediated cascade strategy for the construction of 1,3- and 1,2,3-substituted naphthalenes from readily accessible starting materials. This method employs <em>ortho</em>-alkynyl or arynyl tertiary benzylic alcohols as the substrates, which undergo a Lewis acid-triggered dehydration to form ortho-(alkynyl)-styrene intermediates. These intermediates subsequently undergo intramolecular cycloaromatization, resulting in the formation of substituted naphthalenes in a one-pot reaction. A significant advantage of this approach is its ability to proceed under sustainable and neat reaction conditions using ZnCl₂ as the sole Lewis acid, highlighting the simplicity and practicality of the process. Additionally, the strategy exhibits a broad substrate scope, efficiently yielding the desired naphthalene derivatives with practical and consistent yields. This method not only simplifies the synthetic pathway but also aligns with green chemistry principles by minimizing the use of solvents and reagents.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134285"},"PeriodicalIF":2.1,"publicationDate":"2024-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425572","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 : 2024-09-29DOI: 10.1016/j.tet.2024.134286
Ulises F. Reyes-González , Edson Barrera , Daniela Martínez-López , R. Israel Hernández-Benitez , Julio López , Omar Gómez-García , Dulce Andrade-Pavón , Lourdes Villa-Tanaca , Paola Castillo-Juárez , Francisco Delgado , Joaquín Tamariz
A highly efficient and stereoselective synthesis of (E)-5-(dimethylamino)methylene thiohydantoins is herein reported. It was carried out through a one-pot, two-step reaction between methyl N-arylglycinates, isothiocyanates, and DMFDMA under microwave irradiation. The thermal and catalyst-free reaction of the (dimethylamino)methylene thiohydantoins with anilines led to the stereoselective formation of (E)-(anilinomethylene) thiohydantoins. The antifungal activity of the products was evaluated with a series of five Candida spp., finding a potent effect, even against a fluconazole-resistant C. glabrata strain. The docking studies suggest that this inhibitory effect is due to the binding of the compounds to the active site of fungal HMGR.
{"title":"Synthesis of exocyclic enaminone-based thiohydantoins as potent antifungal agents","authors":"Ulises F. Reyes-González , Edson Barrera , Daniela Martínez-López , R. Israel Hernández-Benitez , Julio López , Omar Gómez-García , Dulce Andrade-Pavón , Lourdes Villa-Tanaca , Paola Castillo-Juárez , Francisco Delgado , Joaquín Tamariz","doi":"10.1016/j.tet.2024.134286","DOIUrl":"10.1016/j.tet.2024.134286","url":null,"abstract":"<div><div>A highly efficient and stereoselective synthesis of (<em>E</em>)-5-(dimethylamino)methylene thiohydantoins is herein reported. It was carried out through a one-pot, two-step reaction between methyl <em>N-</em>arylglycinates, isothiocyanates, and DMFDMA under microwave irradiation. The thermal and catalyst-free reaction of the (dimethylamino)methylene thiohydantoins with anilines led to the stereoselective formation of (<em>E</em>)-(anilinomethylene) thiohydantoins. The antifungal activity of the products was evaluated with a series of five <em>Candida</em> spp., finding a potent effect, even against a fluconazole-resistant <em>C. glabrata</em> strain. The docking studies suggest that this inhibitory effect is due to the binding of the compounds to the active site of fungal HMGR.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134286"},"PeriodicalIF":2.1,"publicationDate":"2024-09-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425573","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 : 2024-09-26DOI: 10.1016/j.tet.2024.134284
Leticia Almazán-Sánchez , María Teresa Ramírez-Apan , David Morales-Morales , Marco A. García-Eleno , Erick Cuevas-Yañez
Using the CuAAC reaction as a key step, a novel series of Nilotinib analogues was prepared by replacing the imidazole ring in the Nilotinib molecule with 1,2,3-triazole moiety via a divergent synthetic approach. The synthesized compounds were tested for cytotoxic activity against a series of tumor cell lines which included U251, PC-3, K562, HCT-15, MCF-7 and SKLU. Inhibition growth up to 85.6 % was observed for some compounds.
{"title":"1,2,3-Triazole nilotinib analogues: Synthesis and Cytotoxic activity","authors":"Leticia Almazán-Sánchez , María Teresa Ramírez-Apan , David Morales-Morales , Marco A. García-Eleno , Erick Cuevas-Yañez","doi":"10.1016/j.tet.2024.134284","DOIUrl":"10.1016/j.tet.2024.134284","url":null,"abstract":"<div><div>Using the CuAAC reaction as a key step, a novel series of Nilotinib analogues was prepared by replacing the imidazole ring in the Nilotinib molecule with 1,2,3-triazole moiety via a divergent synthetic approach. The synthesized compounds were tested for cytotoxic activity against a series of tumor cell lines which included U251, PC-3, K562, HCT-15, MCF-7 and SKLU. Inhibition growth up to 85.6 % was observed for some compounds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134284"},"PeriodicalIF":2.1,"publicationDate":"2024-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425122","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}
Among the various copper-catalyzed coupling reactions, C–S and C–N bond-forming reactions have carried off plentiful recognition due to their demand in the synthesis of molecules having biological and pharmaceutical impact. Organo-copper complex has an incontestable supremacy over the other catalytic complex due to its low cost and the use of readily accessible and stable ligands. As a consequence and in continuation of our explorative studies in this direction, an efficient and novel organo-copper complex has been synthesized and characterized by spectroscopic (NMR, FT-IR) and single crystal X-ray diffraction (XRD) methods. The synthesized stable metal complex has fascinating physical, chemical, biological and catalytic properties. In the chemical exploration refer to protein-metal interactions; we have often used Bovine Serum Albumin (BSA) protein. The synthesized copper complex has the potential to form coordinate bonds with functional groups present in BSA, together with amino acid residues and the protein backbone. The binding of metal complexes to BSA has outstanding imputation in medicinal chemistry. For enhancement of the catalytic activity of the organo-copper complex, we have evaluated it in carbon-hetero bond formation reactions where it proffered an influential tool for the establishment of C–S and C–N bonds.
{"title":"Synthesis and BSA binding study of the Cu(II) complex and applications of it to enhance catalytic activity for C(Sp2)-H bond functionalization and for the synthesis of polyhydroquinolines","authors":"Aminul Islam , Kakoli Malakar , Marappan Velusamy , Pranab Ghosh","doi":"10.1016/j.tet.2024.134278","DOIUrl":"10.1016/j.tet.2024.134278","url":null,"abstract":"<div><div>Among the various copper-catalyzed coupling reactions, <em>C</em>–S and <em>C</em>–N bond-forming reactions have carried off plentiful recognition due to their demand in the synthesis of molecules having biological and pharmaceutical impact. Organo-copper complex has an incontestable supremacy over the other catalytic complex due to its low cost and the use of readily accessible and stable ligands. As a consequence and in continuation of our explorative studies in this direction, an efficient and novel organo-copper complex has been synthesized and characterized by spectroscopic (NMR, FT-IR) and single crystal X-ray diffraction (XRD) methods. The synthesized stable metal complex has fascinating physical, chemical, biological and catalytic properties. In the chemical exploration refer to protein-metal interactions; we have often used Bovine Serum Albumin (BSA) protein. The synthesized copper complex has the potential to form coordinate bonds with functional groups present in BSA, together with amino acid residues and the protein backbone. The binding of metal complexes to BSA has outstanding imputation in medicinal chemistry. For enhancement of the catalytic activity of the organo-copper complex, we have evaluated it in carbon-hetero bond formation reactions where it proffered an influential tool for the establishment of <em>C</em>–S and <em>C</em>–N bonds.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134278"},"PeriodicalIF":2.1,"publicationDate":"2024-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142425567","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 : 2024-09-21DOI: 10.1016/j.tet.2024.134277
Pengfei Sun , Xin Yu , Fang Wei
The development of a transition-metal-catalyzed [3 + 2] cycloaddition for one-pot synthesis of 2-substituted benzofurans from vinyl azides and benzoquinone is reported. This reaction could be carried out under mild conditions without the need to isolate air, giving desired products in good to excellent yields.
{"title":"Facile synthesis of 2-substituted benzofurans by intermolecular [3+2] cycloaddition of benzoquinone and vinyl azides under air","authors":"Pengfei Sun , Xin Yu , Fang Wei","doi":"10.1016/j.tet.2024.134277","DOIUrl":"10.1016/j.tet.2024.134277","url":null,"abstract":"<div><div>The development of a transition-metal-catalyzed [3 + 2] cycloaddition for one-pot synthesis of 2-substituted benzofurans from vinyl azides and benzoquinone is reported. This reaction could be carried out under mild conditions without the need to isolate air, giving desired products in good to excellent yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"167 ","pages":"Article 134277"},"PeriodicalIF":2.1,"publicationDate":"2024-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142322646","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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