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Electrophilic amination of pyrimidine-2-thiones - synthesis of zwitterionic 2-aminothiopyrimidinium-N-ylides, pyrimidine-2-ones and bicyclic pyrimidinium compounds

✍ Scribed by Beate Riemer; Michael Pätzel; Ahmed Hassoun; Jürgen Liebscher; Willy Friedrichsen; Peter G. Jones

Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
957 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

1-Amino-pyrimidine-2-thiones 2 or 11 and I-acylmethyl-pyrimidine-2-thiones 13 react with 3,3pentamethyleneoxaziridine 3 or hydroxylamine-0-sulfonic acid by electrophilic amination of the sulfur atom yielding zwitterionic 2-amino-l-imidothiopyrimidinium-N-ylides 4 and 12 or 1-aminopyrimidine-2ones 5 and I-acylmethylpyrimidme-2-ones 14. The pyrimidine-2-ones 5 and 14 can be cyclized by dehydration to 1,3,4_oxadiazolo[3,2-a]pyrimidmium salts 6 and oxazolo[3,2-alpyrimidinium salts 15.

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