Synthesis of 1-Isocyanomethyl Azoles and Related Compounds

Abstract

1-Isocyanomethyl azoles (14a-f) were synthesized by the reaction of the corresponding azoles (11a-f) with trimethylformamidomethylammonium iodide (8), followed by dehydration of the resulting 1-formamidomethyl azoles (13a-f) using phosphorus oxychloride or triphenylphosphine/carbon tetrachloride. Furthermore, 1-substituted methyl-5-piperidinomethyltetrazoles (15a-f) were prepared by means of the four-component condensation of 14a-f with formaldehyde, sodium azide, and piperidine.