Ethyl 2-Cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-Mediated Lossen Rearrangement: Single-Pot Racemization-Free Synthesis of Hydroxamic Acids and Ureas from Carboxylic Acids
Kishore Thalluri, Srinivasa Rao Manne, Dharm Dev and Bhubaneswar Mandal*
*Department of Chemistry Indian Institute of Technology
Guwahati, Guwahati 781039, India, Email: bmandal
iitg.ernet.in
K. Thalluri, S. R. Manne, D. Dev, B. Mandal, J. Org. Chem., 2014, 79, 3765-3775.
DOI: 10.1021/jo4026429
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Abstract
Hydroxamic acids were synthesized from carboxylic acids and hydroxylamine hydrochloride in the presence of ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate (4-NBsOXY). 4-NBsOXY also promotes the Lossen rearrangement of hydroxamic acids in the presence of amines to yield ureas. The reactions are compatible with common N- and O-protecting groups and prevent racemization.
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D. Dev, N. B. Palakurthy, K. Thalluri, J. Chandra, B. Mandal, J. Org. Chem., 2014, 79, 5420-5431.
Key Words
hydroxamic acids, ureas (amination)
ID: J42-Y2014
