Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles

Authors
Sutcliffe, OB Storr, RC Gilchrist, TL Rafferty, P
Citation
Ob. Sutcliffe et al., Cycloadditions to pyrrolo[1,2-c]thiazoles and pyrazolo[1,5-c]thiazoles, TETRAHEDRON, 56(51), 2000, pp. 10011-10021
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
51
Year of publication
2000
Pages
10011 - 10021
Database
ISI
SICI code
0040-4020(200012)56:51<10011:CTPAP>2.0.ZU;2-S
Abstract
The pyrrolo[1,2-c]thiazole generated by dehydration of dimethyl 5-methyl-1H ,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylate 2-oxide acts as a thiocarbonyl ylide in its cycloaddition to electron deficient alkenes but as an azometh ine ylide with electron deficient alkynes. The analogous pyrazolo[1,5-c]thi azole, generated similarly, acts as a thiocarbonyl ylide with both types of dipolarophile. This behaviour is partially explained by Frontier MO theory . (C) 2000 Elsevier Science Ltd. All rights reserved.