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Fused indoles. 2. Synthesis and reactions of imidazo[1,2‐ a ]‐ and pyrimido[1,2‐ a ]‐indoles
Author(s) -
Coppola Gary M.,
Hardtmann Goetz E.
Publication year - 1979
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.5570160431
Subject(s) - chemistry , diborane , methyllithium , alkylation , ethylamine , propylamine , indole test , medicinal chemistry , demethylation , bicyclic molecule , lithium (medication) , organic chemistry , amine gas treating , catalysis , boron , medicine , biochemistry , gene expression , gene , endocrinology , dna methylation
The alkylation of 2‐chloroindole‐3‐carboxaldehyde ( 1 ) and 3‐acetyl‐2‐chloroindole ( 5 ) with 3‐chloro‐ N,N ‐dimethyl‐1‐propylamine, 3‐chloro‐ N,N ‐diethyl‐1‐propylamine and 2‐chloro‐ N,N ‐dimethyl‐1‐ethylamine is described. Following alkylation, demethylation occurs and furnishes imidazo[1,2,‐ a ]‐ and pyrimido[1,2‐ a ]indoles ( 3a,6,8,10 ). Pyrimido‐indole 3a , on treatment with lithium aluminum hydride, furnishes the bis‐indole 12 . Analogous reaction with diborane affords the reduced product 14 , while reaction with methyllithium yields the deformylated product 13 . Spectral data of the resulting compounds are also discussed.