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Isomerization/recyclization of some 5‐ethoxycarbonyl‐pyrimidines
Author(s) -
Vardanyan R. S.,
Hruby V. J.,
Danagulyan G. G.,
Mkrtchyan A. D.
Publication year - 2005
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.5570420413
Subject(s) - chemistry , pyrimidine , ring (chemistry) , isomerization , nucleophile , medicinal chemistry , stereochemistry , organic chemistry , catalysis
This communication reports on the investigation of a new recyclization conversion of a pyrimidine ring, which can be referred to as CC recyclization. In this reaction the nucleophile cleaves the pyrimidine ring at the N(3)‐C(4) bond, and following rotation around the single C(5)‐C(6) bond the new cyclization takes place. This type of recyclization has general applicability, and takes place upon alkali treatment of substituted 4‐methyl‐5‐ethoxycarbonyl‐ and 4‐amino‐5‐ethoxycarbonyl‐pyrimidines (1) which are transformed respectively to 4‐hydroxy‐5‐acetyl‐ and 4‐hydroxy‐5‐carbamoylpyrimidines (2). The obtained pyrimidyl‐ketones can be readily converted to their hydrazones 7‐12.