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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
Author(s) -
Puchala Agnieszka,
Belaj Ferdinand,
Kappe C. Oliver,
Bergman Jan
Publication year - 2001
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.5570380616
Subject(s) - chemistry , nitric acid , nitration , dehydrogenation , nitrosation , nitric oxide , medicinal chemistry , organic chemistry , catalysis
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