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Pyrimidine derivatives XII. A convenient preparation of 6‐formylpyrimidinedione and 2‐ and 3‐formylpyridine derivatives from corresponding nitrooxymethyl derivatives
Author(s) -
Kinoshita Toshio,
Ohishi Hiroshi
Publication year - 1994
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.5570310654
Subject(s) - chemistry , triethylamine , pyrimidine , octane , organic chemistry , medicinal chemistry , stereochemistry
The convenient preparation of 6‐fomylpyrimidinedione derivatives and 2‐ and 3‐formylpyridine are described. Thus, 5‐bromo‐1,3‐dimethyl‐ ( 1a ), 5‐bromo‐3‐methyl‐1‐(2‐nitrooxyethyl)‐ ( 1b ), and 5‐bromo‐3‐methyl‐1‐(3‐nitrooxypropyl)‐2,4(1 H ,3 H )‐pyrimidine‐dione ( 1c ) were converted to the corresponding 6‐formyl compounds 2a, 2b , and 2c , respectively, in excellent yields by the reaction with triethylamine and 1,4‐diazabicyclo[2.2.2]octane. These 6‐formylpyrimidinedione derivatives are key intermediates for the preparation of 6‐carbon‐carbon substituted compounds, which are expected to be potential antitumor and antiviral agents. Similarly, 2‐(and 3‐)formylpyridine ( 9a (and 9b )) were obtained by the reaction of 2‐(and 3)nitrooxymethylpyridine ( 8a (and 8b )) with 1,4‐diazabicyclo[2.2.2]octane.