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

Issa Yavari, Zohreh Taheri, Sara Sheikhi, Samira Bahemmat, Mohammad R Halvagar

Molecular diversity 2020 Aug

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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.

Citation

Issa Yavari, Zohreh Taheri, Sara Sheikhi, Samira Bahemmat, Mohammad R Halvagar. A synthesis of N-(1H-pyrazol-5-yl)-1,3,4-thiadiazol-2(3H)-imines from nitrile imines and Erlenmeyer thioazlactones. Molecular diversity. 2020 Aug;24(3):727-735