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

Swapan K Samanta; Irene Kylänlahti; Jari Yli-Kauhaluoma

doi:10.1016/j.bmcl.2005.05.066

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

Bioorg Med Chem Lett. 2005 Aug 15;15(16):3717-9. doi: 10.1016/j.bmcl.2005.05.066.

Authors

Swapan K Samanta¹, Irene Kylänlahti, Jari Yli-Kauhaluoma

Affiliation

¹ Faculty of Pharmacy, Drug Discovery and Development Technology Center, P.O. Box 56 (Viikinkaari 5 E), University of Helsinki, Helsinki, FI-00014, Finland.

PMID: 15993061
DOI: 10.1016/j.bmcl.2005.05.066

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Imidazoles / chemical synthesis*
Imidazoles / radiation effects*
Imines / chemical synthesis
Imines / chemistry*
Imines / radiation effects
Microwaves*
Molecular Structure
Nitriles / chemical synthesis
Nitriles / chemistry*
Nitriles / radiation effects
Polymers / chemical synthesis
Polymers / chemistry*
Polymers / radiation effects
Tosyl Compounds / chemical synthesis
Tosyl Compounds / chemistry*
Tosyl Compounds / radiation effects

Substances

Imidazoles
Imines
Nitriles
Polymers
Tosyl Compounds
4-toluenesulfonylmethyl isocyanide