Benzazoles. Part 12. Synthesis of 2-(tetrahydro-2-thienyl)benzimidazoles and their unsaturated derivatives by the reaction of 2- mercaptoalkylbenzimidazoles with β-electrophilic ketones

H. Olga Hankovszky, Kólmón Hideg, László Lex, András Földesi, Pal Sohár

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Abstract

2-(α-Mercaptoalkyl)benzimidazoles (3) reacted with β-halogenoalkylketones (1) or with α,β-unsaturated ketones (2) to form the vinylogue adducts (4) which cyclised to give 2-(3-hydroxytetrahydro- 2-thienyl)benzimidazoles (6). Compounds (4) or (6) reacted with acetic anhydride at room temperature to give the mono- (8) and diacetylated (9) derivatives of (6). At higher temperature dehydroacetylation occurs to give 2-(2,3-dihydro-2-thienyl)benzimidazoles (11).

Original languageEnglish
Pages (from-to)699-704
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - Dec 1 1980

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ASJC Scopus subject areas

  • Chemistry(all)

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