Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives

Abstract

This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance and regioselectivity. Structurally diversified 3-nitropyridine could be time-efficiently (3.5 h) derivatized to various functional 2-O,3-N-pyridines which are apt for further elaborations. The transformation was amenable to gram-scale synthesis.

Keywords

• one-pot
• [3,3]-sigmatropic rearrangement
• heteroarene
• pyridine derivatives
• late-stage functionalization