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Synthesis of some 3‐Hydroxy‐5‐pyridylpyrrole derivatives
Author(s) -
Campaigne E.,
Shutske G. M.,
Payne John C.
Publication year - 1977
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.5570140235
Subject(s) - chemistry , adduct , ethyl ester , organic chemistry
Abstract Ethyl sarcosinate adds to 2, −3‐ and 4‐pyridylmethylidenemalonates to produce the Michael adducts, which can be conveniently cyclized to oxopyrrolidine diesters under Dieckmann conditions. Mild oxidation converted the crude adducts to the isomeric 1‐methyl‐3‐hydroxy‐5‐pyridylpyrrole‐2,4‐dicarboxylates. Addition of ethyl glycinate to ethyl picolinoylacetate or ethyl nicotinoylacetate produced the corresponding enaminoesters, but these azadiesters were not cyclized under the usual Dieckmann conditions.