Intermolecular dipolar cycloaddition reactions of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates

Authors
Melo, TMVDPE Soares, MIL Barbosa, DM Gonsalves, AMDR Beja, AM Paixao, JA Silva, MR da Veiga, LA
Citation
Tmvdpe. Melo et al., Intermolecular dipolar cycloaddition reactions of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates, TETRAHEDRON, 56(21), 2000, pp. 3419-3424
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
21
Year of publication
2000
Pages
3419 - 3424
Database
ISI
SICI code
0040-4020(20000519)56:21<3419:IDCRO5>2.0.ZU;2-F
Abstract
(5R)-3-Methyl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olate was genera ted in the presence of a range of dipolarophiles. The intermolecular 1,3-di polar cycloaddition of this mesoionic species led to the synthesis of chira l 1H-pyrrolo[1,2-c]thiazole derivatives 7a, 7b, 8, 14, 18, 19 and 20. In th e reaction with methyl and ethyl vinyl ketone, spiro compounds 9 and 15 wer e also obtained. The structure of compound 15 was determined by X-ray cryst allography. (C) 2000 Published by Elsevier Science Ltd.