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Propylphosphonic Anhydride (T3P)-Mediated One-Pot Rearrangement of Carboxylic Acids to Carbamates

John Kallikat Augustine*, Agnes Bombrun, Ashis Baran Mandal, Padma Alagarsamy, Rajendra Nath Atta, Panneer Selvam

*Syngene International Ltd., Biocon Park, Plot Nos. 2 & 3, Bommasandra IV Phase, Jigani Link Road, Bangalore - 560 099, India, Email: john.kallikatsyngeneintl.com

J. K. Augustine, A. Bombrun, A. B. Mandal, P. Alagarsamy, R. N. Atta, P. Selvam, Synthesis, 2011, 1477-1483.

DOI: 10.1055/s-0030-1259964


Abstract

A simple one-pot conversion of carboxylic acids to carbamates is achieved in the presence of propylphosphonic anhydride (T3P) in combination with azidotrimethylsilane and an alcohol via the Curtius rearrangement. Besides diverse primary to tertiary alcohols, the reaction tolerated a wide scope of aromatic, heterocyclic, and aliphatic carboxylic acids which underwent rearrangement in excellent yields.

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Key Words

propylphosphonic anhydride, Curtius rearrangement, carbamates, peptide coupling agents, azidotrimethylsilane, multicomponent reactions


ID: J66-Y2011-1290