Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles
摘要:
A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.
OXIDATIVE CONDENSATION REACTIONS OF AMINES WITH CARBIDITHIOATES AND XANTHATES<sup>1</sup>
作者:GLEN ALLIGER、G. E. P. SMITH、E. L. CARR、H. P. STEVENS
DOI:10.1021/jo01158a005
日期:1949.11
Manufacture of dithio derivatives from aldehydes
申请人:QUAKER OATS CO
公开号:US01756158A1
公开(公告)日:1930-04-29
DE403123
申请人:——
公开号:——
公开(公告)日:——
Synthesis of N-Functionalized/NH-Multisubstituted Indoles, Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular Amination of 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles
作者:S. Vijay Kumar、B. Saraiah、G. Parameshwarappa、H. Ila、Girijesh K. Verma
DOI:10.1021/jo501114a
日期:2014.9.5
A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.
Bruni; Levi, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1923, vol. <5> 32 I, p. 7