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Tandem Silver‐Catalyzed Cyclization/Nucleophilic Functionalization of 2‐Alkynylindole‐3‐carbaldehyde Oximes to Afford New 2,4‐Disubstituted γ‐Carbolines
Author(s) -
Rodrigues Nuno,
Boiaryna Liliana,
Vercouillie Johnny,
Guilloteau Denis,
Suzenet Franck,
Buron Frederic,
Routier Sylvain
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600904
Subject(s) - chemistry , nucleophile , tandem , indole test , catalysis , combinatorial chemistry , nucleophilic addition , surface modification , medicinal chemistry , organic chemistry , materials science , composite material
Highly substituted pyrido[4,3‐ b ]indole derivatives were synthesized through a straightforward one‐pot silver‐catalyzed process involving 2‐alkynylindole‐3‐carbaldehyde oximes. The tandem cyclization/nucleophilic addition sequence was optimized and applied to a wide range of nucleophiles, which reacted regioselectively at the pyrido[4,3‐ b ]indole C4 position. The scope and limitations of the methodology were evaluated and the final compounds were obtained in fair to very good yields. This versatile method proved to be compatible with various chemical functionalities or (hetero)cycles.