Double "Open and Shut" Transformation of gamma-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

作者:Abe Takumi*; Shimizu Haruka; Takada Shiori; Tanaka Takahiro; Yoshikawa Mai; Yamada Koji*
来源:Organic Letters, 2018, 20(6): 1589-1592.
DOI:10.1021/acs.orglett.8b00332

摘要

A novel cascade reaction of indole-2,3-epoxide equivalents with gamma-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

  • 出版日期2018-3-16