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Gold‐Catalysis: Highly Efficient and Regio‐Selective Carbonyl Migration in Alkynyl‐Substituted Indole‐3‐Carboxamides Leading to Azepino[3,4‐ b ]indol‐1‐ones
Author(s) -
Hashmi A. Stephen K.,
Yang Weibo,
Rominger Frank
Publication year - 2012
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200092
Subject(s) - chemistry , indole test , alkyne , catalysis , combinatorial chemistry , stereochemistry , organic chemistry
An unprecedented rearrangement/anellation sequence allows the clean synthesis of azepino[3,4‐ b ]indol‐1‐ones from readily available starting materials. Alkyne‐substituted indole‐3‐carboxamides were prepared and converted to azepino[3,4‐ b ]indol‐1‐ones by the SPhosAuNTf 2 catalyst (SPhos=2‐dicyclohexylphosphino‐2′,6′‐dimethoxybiphenyl). The new connectivity, which involves an unprecedented 3,2‐shift of an acylamino group for the product formation, was proven by a crystal structure analysis.