Synthesis of novel 2,2- and 1,1-linked dimeric ‘head-to-head’ N-alkoxybenzimidazoles |
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Authors: | John M. Gardiner Andrew D. GossTahir N. Majid Andrew D. Morley |
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Affiliation: | a Department of Chemistry, UMIST, Manchester M60 1QD, UK b Aventis Pharma US, Route 202-206, Bridgewater, NJ 08807, USA c Aventis Pharma, Rainham Road South, Dagenham, Essex RM10 7XS, UK |
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Abstract: | Synthesis of two new types of ‘head-to-head’ N,N-alkoxy bisbenzimidazoles is described. The proposed intermediate N-oxy benzimidazole from base-induced heterocyclization of N-alkylnitroanilines can be trapped with a biselectrophile (to give an N,N-linked dimer), or double heterocyclization of dimeric nitroanilines can be intercepted by electrophile trapping of both N-oxybenzimidazole termini to give C2,C2-linked dimers. These represent two regioisomeric motifs constituting new classes of benzimidazole dimers. |
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