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Aniline Dearomatization and Silver‐Catalyzed [3+3] Dipolar Cycloaddition: Efficient Construction of Oxocino[4,3,2‐ cd ]indoles from 2‐Alkynylanilines and 2‐Alkynylbenzaldoximes
Author(s) -
Han Dandan,
He Qiuqin,
Fan Renhua
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201507277
Subject(s) - aromatization , aniline , cycloaddition , catalysis , combinatorial chemistry , indole test , chemistry , organic chemistry
2‐Alkynylanilines are attractive starting materials in indole synthesis because of their ready availability. Herein, a one‐pot stepwise procedure is reported for efficient construction of multisubstituted oxocino[4,3,2‐ cd ]indoles from 2‐alkynylanilines and 2‐alkynylbenzaldoximes. The method comprises the oxidative dearomatization of 2‐alkynylanilines, the silver‐catalyzed [3+3] cycloaddition with 2‐alkynylbenzaldoximes, and subsequent thermal radical skeletal rearrangement and aromatization.