Synthesis of Annelated Imidazoles and Benzimidazoles

James R. McClure; John H. Custer; H. Dean Schwarz; Deborah A. Lill

doi:10.1055/s-2000-6629

Synlett 2000; 2000(5): 0710-0712
DOI: 10.1055/s-2000-6629

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Synthesis of Annelated Imidazoles and Benzimidazoles

James R. McClure^* , John H. Custer, H. Dean Schwarz, Deborah A. Lill

^*Department of Chemistry, Southern Illinois University, Edwardsville, Il, 62026-1652, USA; Fax + 1(618)6 50 35 56; E-mail: jmcclur@SIUE.edu

Abstract

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A variety of fused ring imidazole or benzimidazole derivatives were prepared through two successive condensations of a dihalide with 4,5-diphenylimidazole or benzimidazole. The 2-methyl substituted derivatives of 4,5-diphenylimidazole or benzimidazole were also used. The size of the annelated ring, which is dependent on the dihalide used, can be varied from five to seven atoms. Initially, N-alkylhalo derivatives were prepared by condensation of the heterocyclic starting materials with a dihalide. Ring closure was then effected through intramolecular condensation of a carbanion derived from the 2-position or the 2-methyl group of the parent heterocyclic ring with the N-alkylhalo moiety.

heterocycles - carbanions - ring closure - imidazoles - benzimidazoles

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