1, 3-Dipolar Cycloaddition of Diazomethane with Carbon-Carbon Unsaturated Systems Involving Nitrofuran Ring

Studies on Heteroaromaticity. XIII

Abstract

1, 3-Dipolar cycloaddition reaction of diazomethane with 5-nitro-2-furylacrylic acid gave 4- (5'-nitro-2'-furyl) -3-carbomethoxypyrazoline (3), mp 184485°C, in 80% yield. A similar reaction with 5-nitro-2-furylpropiolic acid afforded the corresponding isomeric mixture of the 2-pyrazole derivatives in 25% yield. (1) was refluxed in toluene to afford 2- (5'-nitro-2'-furyl) -cyclopropane carboxylate, mp 144 145°C, in 88% yield.