Microwave-assisted synthesis of imidazoles: reaction of p-toluenesulfonylmethyl isocyanide and polymer-bound imines.
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.
Faculty of Pharmacy, Drug Discovery and Development Technology Center, P.O. Box 56 (Viikinkaari 5 E), University of Helsinki, Helsinki, FI-00014, Finland.
Swapan K
SK
Samanta
Irene
I
Kylänlahti
Jari
J
Yli-Kauhaluoma
D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000528:radiation effects*; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D008872:Microwaves; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D014105:Tosyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects
D007093:Imidazoles; D007097:Imines; D009570:Nitriles; D011108:Polymers; D014105:Tosyl Compounds; C061881:4-toluenesulfonylmethyl isocyanide