An efficient chiral Br?nsted acid-catalyzed conjugate addition of indoles to azadienes has been successfully developed,which enables a facile approach to optically active hetero-triarylmethanes with excellent enantios...An efficient chiral Br?nsted acid-catalyzed conjugate addition of indoles to azadienes has been successfully developed,which enables a facile approach to optically active hetero-triarylmethanes with excellent enantioselectivities and broad substrate scope.This chiral Br?nsted acid catalytic system provides a new opportunity for the development of asymmetric reactions of azadienes.展开更多
The reaction between 2-aminobenzothiazole with dialkyl acetylenedicarboxylates in the presence of isocyanides,leads to functionalized azadienes in good yields.
Herein,we report a substrate-controlled palladium-catalyzed divergent decarboxylative cycloaddition of vinyloxazolidine-2,4-diones with azadienes.The reaction of benzofuran-derived azadienes undergoes a decarboxylativ...Herein,we report a substrate-controlled palladium-catalyzed divergent decarboxylative cycloaddition of vinyloxazolidine-2,4-diones with azadienes.The reaction of benzofuran-derived azadienes undergoes a decarboxylative(3+2)cycloaddition process to access spiro[benzofuran-butyrolactam]derivatives in good yields with acceptable diastereoselectivities.In contrast,the reaction of benzothiophene-based azadienes proceeds a decarboxylative(5+4)cycloaddition pathway to give benzothieno[1,2-d]diazonin-5-ones in moderate to high yields.Gram-scale synthesis and further transformations demonstrated the potential synthetic utility of the developed protocol.展开更多
A catalyst-free and atom-economical[4+3]cycloaddition of azadienes with C,N-cyclic azomethine imines has been developed,providing an efficient and environmentally benign access to 1,2,4-triazepines with high diastereo...A catalyst-free and atom-economical[4+3]cycloaddition of azadienes with C,N-cyclic azomethine imines has been developed,providing an efficient and environmentally benign access to 1,2,4-triazepines with high diastereoselectivities and yields.This reaction can be performed in 2-methyltetrahydrofuran under mild conditions smoothly.展开更多
Benzo[b]thiophene fused compounds with a unique active heterocyclic skeleton have wide applications in the fields of medicinal chemistry,organic synthesis,and organic functional materials,which resulted in rapid devel...Benzo[b]thiophene fused compounds with a unique active heterocyclic skeleton have wide applications in the fields of medicinal chemistry,organic synthesis,and organic functional materials,which resulted in rapid development of many efficient methods for the construction of benzo[b]thiophenefused heterocycles in recent years.Among these methods,the domino reaction of benzo[b]thiophene derivatives is a practical and powerful synthetic route to access benzo[b]thiophene-fused heterocycles by virtue of the particularity of sulfur atom.This review summarizes the latest developments in the construction of benzo[b]thiophene-fused heterocycles by ring formation at the C2-C3-position of benzo[b]thiophene derivatives in the past decade.Additionally,this review is divided into four parts according to the four kinds of benzo[b]thiophene derivatives used,including thioaurone,thioisatin,substituted benzo[b]thiophene,and azadiene.展开更多
Unprecedented cycloaddition reactions of azatrienes (1) with sulfene leading to the synthesis of functionalized thiazinedioxide derivatives (5) are described. The reactions were found be highly regioselective resultin...Unprecedented cycloaddition reactions of azatrienes (1) with sulfene leading to the synthesis of functionalized thiazinedioxide derivatives (5) are described. The reactions were found be highly regioselective resulting in the formation of only [4 + 2] cycloadducts.展开更多
文摘An efficient chiral Br?nsted acid-catalyzed conjugate addition of indoles to azadienes has been successfully developed,which enables a facile approach to optically active hetero-triarylmethanes with excellent enantioselectivities and broad substrate scope.This chiral Br?nsted acid catalytic system provides a new opportunity for the development of asymmetric reactions of azadienes.
文摘The reaction between 2-aminobenzothiazole with dialkyl acetylenedicarboxylates in the presence of isocyanides,leads to functionalized azadienes in good yields.
基金the Sichuan Science and Technology Program(No.2024NSFSC1123)the Natural Science Foundation of China(Nos.22171029,and 22271027)the Opening Foundation of the Key Laboratory of Asymmetric Synthesis and Chiral Technology of Sichuan Province(No.2024KFKT01)for the financial support.
文摘Herein,we report a substrate-controlled palladium-catalyzed divergent decarboxylative cycloaddition of vinyloxazolidine-2,4-diones with azadienes.The reaction of benzofuran-derived azadienes undergoes a decarboxylative(3+2)cycloaddition process to access spiro[benzofuran-butyrolactam]derivatives in good yields with acceptable diastereoselectivities.In contrast,the reaction of benzothiophene-based azadienes proceeds a decarboxylative(5+4)cycloaddition pathway to give benzothieno[1,2-d]diazonin-5-ones in moderate to high yields.Gram-scale synthesis and further transformations demonstrated the potential synthetic utility of the developed protocol.
基金We thank the Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology(QNLM)(No.2022QNLM030003-2)the Fundamental Research Funds for the Central Universities,Ocean University of China,Qingdao National Laboratory for Marine Science and Technology(Nos.LMDBCXRC201902 and LMDBCXRC201903)+2 种基金Taishan Scholar Program of Shandong Province(Nos.tsqn201909056 and tsqn202103152)National Natural Science Foundation of China(No.22171251)Natural Science Foundation of Shandong Province(No.ZR2021QB033)for financial support.
文摘A catalyst-free and atom-economical[4+3]cycloaddition of azadienes with C,N-cyclic azomethine imines has been developed,providing an efficient and environmentally benign access to 1,2,4-triazepines with high diastereoselectivities and yields.This reaction can be performed in 2-methyltetrahydrofuran under mild conditions smoothly.
基金financially supported by the National Natural Science Foundation of China(Nos.21403154 and 22003045)the Natural Science Foundation of Tianjin(No.13JCYBJC38700)the Tianjin Municipal Education Commission(No.2018KJ137)。
文摘Benzo[b]thiophene fused compounds with a unique active heterocyclic skeleton have wide applications in the fields of medicinal chemistry,organic synthesis,and organic functional materials,which resulted in rapid development of many efficient methods for the construction of benzo[b]thiophenefused heterocycles in recent years.Among these methods,the domino reaction of benzo[b]thiophene derivatives is a practical and powerful synthetic route to access benzo[b]thiophene-fused heterocycles by virtue of the particularity of sulfur atom.This review summarizes the latest developments in the construction of benzo[b]thiophene-fused heterocycles by ring formation at the C2-C3-position of benzo[b]thiophene derivatives in the past decade.Additionally,this review is divided into four parts according to the four kinds of benzo[b]thiophene derivatives used,including thioaurone,thioisatin,substituted benzo[b]thiophene,and azadiene.
文摘Unprecedented cycloaddition reactions of azatrienes (1) with sulfene leading to the synthesis of functionalized thiazinedioxide derivatives (5) are described. The reactions were found be highly regioselective resulting in the formation of only [4 + 2] cycloadducts.
