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On the reaction of 3,4-dihydropyrimidones with nitric acid. Preparation and x-ray structure analysis of a stable nitrolic acid

✍ Scribed by Agnieszka Puchala; Ferdinand Belaj; C. Oliver Kappe; Jan Bergman

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 118 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380616

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✦ Synopsis

Abstract

A series of substituted 3,4‐dihydro‐2‐pyrimidones (DHPMs) was reacted with nitric acid under different reaction conditions. Treatment of DHPMs with 50‐65% nitric acid at 0 °C led to the formation of the corresponding dehydrogenated 2‐pyrimidones in moderate to good yields. In contrast, reaction of one representative DHPM with 60% nitric acid at 50 °C led to an unusually stable nitrolic acid, involving a formal nitration, nitrosation, and dehydrogenation step. The molecular structure of this product was determined by X‐ray crystallographic analysis

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