Preparation of 5-Substituted 2-Mercapto-1-methylimidazoles. Direct Metalation of 2-Mercapto-1-methylimidazole

Abstract
2-Mercapto-1-methylimidazole (1) is directly metalated with tert- butyllithium in tetrahydrofuran to give the 5, S-dianion 2. Reaction of the dianion 2 with a series of electrophiles gives regioselectively 5-substituted 2-mercapto-1-methylimidazoles 4, 5 and 7.

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