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Action of 1,2‐diamines and o ‐aminophenols on 1‐alkyl‐3‐carboxyindole‐2‐acetic acid anhydrides. Preparation of new ring systems
Author(s) -
AbdelFattah A. M.,
Hussain S. M.,
ElReedy A. M.
Publication year - 1982
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.5570190617
Subject(s) - chemistry , ethylenediamine , acetanilide , alkyl , ring (chemistry) , acetic acid , acetic anhydride , medicinal chemistry , stereochemistry , organic chemistry , catalysis
1‐Alkyl‐3‐carboxyindole‐2‐acetic acid anhydrides (I) react with ethylenediamine and with o ‐phenylenediamine to give directly 10‐alkylimidazo[3,2:1′,2′]pyrido[4,5‐ b ]indol‐5(1 H )‐ones (II) and 5,6‐dihydro‐5‐alkyl‐13 H ‐indolo[2′,3′:4,5]pyrido[1,2‐ a ]benzimidazol‐13‐one (V), respectively. However, anhydrides I react with o ‐aminophenol and with o ‐aminothiophenol to give carboxyindole‐acetanilide derivatives IX, which can be cyclised to indolo[2′,3′:4,5]pyrido[2,1‐ b ]benzoxazolone and indolo[2′,3′:4,5]pyrido[2,1‐ b ]benzthiazolone (XI). Some derivatives of II and V were prepared to help in elucidating the structures.