ELECTROPHILIC AMINATION OF PYRIMIDINE-2-THIONES - SYNTHESIS OF ZWITTERIONIC 2-AMINOTHIOPYRIMIDINIUM-N-YLIDES, PYRIMIDINE-2-ONES AND BICYCLIC PYRIMIDINIUM COMPOUNDS

Authors
RIEMER B PATZEL M HASSOUN A LIEBSCHER J FRIEDRICHSEN W JONES PG
Citation
B. Riemer et al., ELECTROPHILIC AMINATION OF PYRIMIDINE-2-THIONES - SYNTHESIS OF ZWITTERIONIC 2-AMINOTHIOPYRIMIDINIUM-N-YLIDES, PYRIMIDINE-2-ONES AND BICYCLIC PYRIMIDINIUM COMPOUNDS, Tetrahedron, 49(18), 1993, pp. 3767-3780
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
18
Year of publication
1993
Pages
3767 - 3780
Database
ISI
SICI code
0040-4020(1993)49:18<3767:EAOP-S>2.0.ZU;2-F
Abstract
1-Amino-pyrimidine-2-thiones 2 or 11 and 1-acylmethyl-pyrimidine-2-thi ones 13 react with 3,3-pentamethyleneoxaziridine 3 or hydroxylamine-O- sulfonic acid by electrophilic amination of the sulfur atom yielding z witterionic 2-amino-1-imidothiopyrimidinium-N-ylides 4 and 12 or 1-ami nopyrimidine-2-ones 5 and 1-acylmethylpyrimidine-2-ones 14. The pyrimi dine-2-ones 5 and 14 can be cyclized by dehydration to 1,3,4-oxadiazol o[3,2-a]pyrimidinium salts 6 and oxazolo[3,2-a]pyrimidinium salts 15.