Nucleophilic functionalization of benzylidene dihydrothiazole through DDQ-promoted formation of an original ambivalent electrophilic intermediate

Authors
Vanier, C Wagner, A Mioskowski, C
Citation
C. Vanier et al., Nucleophilic functionalization of benzylidene dihydrothiazole through DDQ-promoted formation of an original ambivalent electrophilic intermediate, SYNLETT, (6), 2001, pp. 842-844
Citations number
33
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
6
Year of publication
2001
Pages
842 - 844
Database
ISI
SICI code
0936-5214(200106):6<842:NFOBDT>2.0.ZU;2-D
Abstract
Benzylidene dihydrothiazoles undergo DDQ-promoted hydrogen abstraction to y ield an original ambivalent electrophilic intermediate. Treated with nucleo philes this covalent intermediate undergoes two possible substitution react ions one at the 5-methyl position and one at the DDHQ aromatic center. For a given benzylidene dihydrothiazole the ratio of the two products depends o n the nature of the nucleophile.