Bioorganic & Medicinal Chemistry Letters 2005-08-15

Microwave-assisted synthesis of imidazoles: reaction of p-toluenesulfonylmethyl isocyanide and polymer-bound imines.

Swapan K Samanta, Irene Kylänlahti, Jari Yli-Kauhaluoma

Index: Bioorg. Med. Chem. Lett. 15(16) , 3717-9, (2005)

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Abstract

A convenient method for the synthesis of 1,5-disubstituted imidazoles has been developed on a polymeric support using base-promoted 1,3-dipolar cycloaddition reaction of p-toluenesulfonylmethyl isocyanide (TOSMIC) with immobilized imines under microwave irradiation. The immobilized imines were synthesized by the reaction of various primary benzyl amines with 4-formyl-3-methoxyphenoxymethyl polystyrene in the presence of trimethyl orthoformate at room temperature. Cleavage from the polymeric support using trifluoroacetic acid gave the desired 1,5-disubstituted imidazoles with excellent yield and high purity.