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New electrophilic reactions of 2,2′‐bisindolyls with acid chlorides and carbodienophiles
Author(s) -
Pindur U.,
Kim Y.S.
Publication year - 1996
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570330317
Subject(s) - chemistry , anthranilic acid , acylation , dehydrogenation , electrophile , aryne , aldehyde , indole test , derivative (finance) , medicinal chemistry , propellane , organic chemistry , bicyclic molecule , catalysis , financial economics , economics
Some new acylation and cyclization reactions of 2,2′‐bisindolyls 1, 2 are described. The product patterns constitute acyl derivatives 3, 4, 5 and an aldehyde 7 , indolo[2,3‐ a ]carbazoles 6, 14, 17, 19, 20 and cyclopentadiindoles 22 and 24 . In the reaction with aryne or diazotated anthranilic acid, a 3‐benzoylindole derivative 9 and phenylindolyl azo dye 10 are formed. N ‐methylmaleimide reacts with 2,2′‐bisindolyl 2 via Michael type addition, dehydrogenation and cyclization to several functionalized or anellated indole derivatives 11, 12, 13 and 14 , respectively.