PSEUDOHALOGEN CHEMISTRY .11. SOME ASPECTS OF THE CHEMISTRY OF ALPHA-THIOCYANATO-BETA-DICARBONYL COMPOUNDS

Authors
ATKINS EF DABBS S GUY RG MAHOMED AA MOUNTFORD P
Citation
Ef. Atkins et al., PSEUDOHALOGEN CHEMISTRY .11. SOME ASPECTS OF THE CHEMISTRY OF ALPHA-THIOCYANATO-BETA-DICARBONYL COMPOUNDS, Tetrahedron, 50(24), 1994, pp. 7253-7264
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
24
Year of publication
1994
Pages
7253 - 7264
Database
ISI
SICI code
0040-4020(1994)50:24<7253:PC.SAO>2.0.ZU;2-T
Abstract
Enolised alpha-thiocyanato-beta-dicarbonyl compounds dimerise in ethan ol at room temperature to give tautomeric 4,5-disubstituted 2-amino- a nd 2-acetamido-thiazoles by a C-S-C + C-N cyclisation. Tautomerism is due to the unusual 4-(beta-dicarbonyl-alpha-thio) substituent. Competi ng intramolecular cyclisations lead to minor amounts of heterocycles c ontaining the thiazole and/or oxathiole ring systems.