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4-Aryl-3-thiocyanatobutan-2-ones were prepared by Meerwein reactions from methyl vinyl ketone and aryldiazonium salts under copper(II) catalysis in 35-75% yields. α-Thiocyanato ketones regioselectively react with 1-methyl-3-aminopyrazole forming N-(3-pyrazolyl)-substituted 2-aminothiazoles in 80-91%… Click to show full abstract
4-Aryl-3-thiocyanatobutan-2-ones were prepared by Meerwein reactions from methyl vinyl ketone and aryldiazonium salts under copper(II) catalysis in 35-75% yields. α-Thiocyanato ketones regioselectively react with 1-methyl-3-aminopyrazole forming N-(3-pyrazolyl)-substituted 2-aminothiazoles in 80-91% yields. An ester group in position 3 of the pyrazole induced a regioselective ring-closure reaction followed by an intramolecular cyclization, which gave first representatives of a new heterocyclic system, pyrazolo[4,3-e]thiazolo[3,2-a]pyrimidine, in 74-93% yields. In addition, the preparations of 5-benzyl-4-methylthiazol-2-ones in 84-93% yields are described.
Journal Title: Organic letters
Year Published: 2022
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