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Preparation of compounds in the new dipyrrolo[3,4‐ b :3′,4′‐ e ]‐pyridine series from 1‐benzylidene‐2,3‐dioxopyrrolidines. A variation of the hantzsch synthesis
Author(s) -
Snyder Carroll A.,
Thorn Mark A.,
Klijanowicz James E.,
Southwick Philip L.
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.5570190330
Subject(s) - chemistry , pyridine , aromatization , ring (chemistry) , medicinal chemistry , ammonium formate , formate , stereochemistry , organic chemistry , formic acid , catalysis
Treatment of easily prepared l‐substituted‐4‐benzylidene‐2,3‐dioxopyrrolidines with ammonium formate produces 1,2,4,6,7,8‐hexahydro‐2,6‐disubstituted‐8‐aryldipyrrolo [3,4‐ b :3′,4′‐ e ]pyridine‐3,5‐diones (II), usually in yields of 50 to 60%. Aromatization of the dihydropyridine ring of the hexahydroderivatives II yields corresponding 1,2,6,7‐tetrahydro‐2,6‐disubstituted‐8‐aryldipyrrolo[3,4‐ b :3′,4′‐ e ]pyridine‐3,5‐diones (III). These compounds appear to be the first to incorporate the dipyrrolo[3,4‐ b :3′,4′‐ e ]pyridine ring system.