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Synlett 2001; 2001(6): 0842-0844
DOI: 10.1055/s-2001-14609
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Nucleophilic Functionalization of Benzylidene Dihydrothiazole through DDQ-Promoted Formation of an Original Ambivalent Electrophilic Intermediate

Cécile Vanier* , Alain Wagner, Charles Mioskowski
  • *Laboratoire de Synthèse Bio-organique, Université Louis Pasteur de Strasbourg, UMR 7514 associée au CNRS, Faculté de Pharmacie, 74 route du Rhin - B.P. 24 - 67401 Illkirch cedex, France; Fax + 3 33 90 24 43 06; E-mail: mioskow@aspirine.u-strasbg.fr; alwag@aspirine.u-strasbg.fr
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Publication Date:
31 December 2001 (online)

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Benzylidene dihydrothiazoles undergo DDQ-promoted hydrogen abstraction to yield an original ambivalent electrophilic intermediate. Treated with nucleophiles this covalent intermediate undergoes two possible substitution reactions 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 on the nature of the nucleophile.

electron transfer - heterocycles - nucleophilic addition - oxidation - quinone