Abstract
This communication reports on the investigation of a new recyclization conversion of a pyrimidine ring, which can be referred to as C-C 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.
Original language | English (US) |
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Pages (from-to) | 557-562 |
Number of pages | 6 |
Journal | Journal of Heterocyclic Chemistry |
Volume | 42 |
Issue number | 4 |
DOIs | |
State | Published - 2005 |
ASJC Scopus subject areas
- Organic Chemistry