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An efficient, facile, and practical liquid-phase combinatorial synthesis of benzimidazoles under microwave irradiation is described. In the first step of reaction sequence, polymer-bound activated aryl fluoride was condensed with selective primary amines via an ipso-fluoro displacement reaction. Reduction of the polymer-bound nitro group followed by cyclization with isothiocyanates afforded immobilized benzimidazoles. The desired products were obtained in high yield with high purity after detaching from the soluble matrix. All reactions involved (S(N)Ar reaction, reduction, cyclization, and support cleavage) were performed completely within a few minutes under microwave irradiation. The coupling of microwave technology with liquid-phase combinatorial synthesis constitutes a novel and particularly attractive avenue for the rapid generation of structurally diverse libraries.
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Bendale et al. (2002) studied this question.
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