SYNTHESIS OF BENZO[D]-1,2-THIAZOLE-1,1-DIOXIDE DERIVATIVES VIA DIRECTED LITHIATION OF 2,2-DIMETHYL-N-(PHENYLSULFONYL)-PROPANAMIDES

Authors
STANETTY P KRUMPAK B EMERSCHITZ T MEREITER K
Citation
P. Stanetty et al., SYNTHESIS OF BENZO[D]-1,2-THIAZOLE-1,1-DIOXIDE DERIVATIVES VIA DIRECTED LITHIATION OF 2,2-DIMETHYL-N-(PHENYLSULFONYL)-PROPANAMIDES, Tetrahedron, 53(10), 1997, pp. 3615-3626
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
10
Year of publication
1997
Pages
3615 - 3626
Database
ISI
SICI code
0040-4020(1997)53:10<3615:SOBDVD>2.0.ZU;2-H
Abstract
A novel synthesis of 7-substituted benzo[d]-1,2-thiazole-1,l-dioxides 4 is presented including directed lithiation of 2,2-dimethyl-N-(phenyl sulfonyl)-propanamides 1 - 3, aryne-mediated cyclization and subsequen t quenching of aryllithium intermediates with various electrophiles. A proposed mechanism is rationalized by some control experiments. (C) 1 997 Elsevier Science Ltd.