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Preparation of 3‐(2 H ‐pyran‐2‐on‐6‐yl)indolizines and the diels‐alder reactions with some olefinic and acetylenic dienophiles
Author(s) -
Shimo Tetsuro,
Ohe Masayuki,
Somekawa Kenichi,
Tsuge Otohiko
Publication year - 1991
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.5570280803
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , cycloaddition , pyran , bicyclic molecule , acetylenedicarboxylate , diels–alder reaction , medicinal chemistry , ring (chemistry) , organic chemistry , catalysis
3‐(2 H ‐Pyran‐2‐on‐6‐yl)indolizines 6a‐d were prepared by 1,3‐dipolar cycloaddition reactions of N ‐(2 H ‐pyran‐2‐on‐6‐yl)methylpyridinium bromides 5a,b with dimethyl acetylenedicarboxylate (DMAD). All of the cycloaddition reactions of 6b with N ‐phenylmaleimide, p ‐benzoquinone, and DMAD took place at the 2‐pyrone ring to give 3‐substituted indolizines.