Access to N-Thioalkenyl and N-(o-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C-O Bond Cleavage of an Alkoxide - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2015

Access to N-Thioalkenyl and N-(o-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C-O Bond Cleavage of an Alkoxide

Résumé

We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C-O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient and rapid access to the privileged benzimidazol-2-one scaffold.

Domaines

Chimie
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Dates et versions

hal-01462224 , version 1 (08-02-2017)

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Citer

Federico Andreoli, Radia Kaid-Slimane, Fabien Coppola, Daniel Farran, Christian Roussel, et al.. Access to N-Thioalkenyl and N-(o-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C-O Bond Cleavage of an Alkoxide. Journal of Organic Chemistry, 2015, 80 (6), pp.3233-3241. ⟨10.1021/acs.joc.5b00221⟩. ⟨hal-01462224⟩
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