A synthesis of N-(1H-pyrazol-5-yl)-1,3,4-thiadiazol-2(3H)-imines from nitrile imines and Erlenmeyer thioazlactones

Abstract

Erlenmeyer thioazlactones are reacted with hydrazonoyl chlorides in the presence of Et₃N to afford functionalized N-(1H-pyrazol-5-yl)-1,3,4-thiadiazol-2(3H)-imines in excellent yields. This strategy is based on a domino double 1,3-dipolar cycloaddition reaction of nitrile imines to Erlenmeyer thioazlactones, followed by the elimination of carbon monoxide and phenylmethanthiol from the initially formed cycloadducts. This method provides fast access to a variety of structurally diverse N-(1H-pyrazol-5-yl)-1,3,4-thiadiazol-2(3H)-imines. The structure of a typical product was established by X-ray crystallography.

Keywords: 1,3-Dipolar cycloaddition; 2-Amino-1,3,4-thiadiazole; Arylidenethioazlactones; Nitrile imines; Pyrazoles.