Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY): A Recyclable Coupling Reagent for Racemization-Free Synthesis of Peptide, Amide, Hydroxamate, and Ester

Dharm Dev, Nani Babu Palakurthy, Kishore Thalluri, Jyoti Chandra and Bhubaneswar Mandal*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, Assam 781039, India, Email: bmandaliitg.ernet.in

D. Dev, N. B. Palakurthy, K. Thalluri, J. Chandra, B. Mandal, J. Org. Chem., 2014, 79, 5420-5431.

DOI: 10.1021/jo500292m

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Abstract

The coupling reagent ethyl 2-cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY) produces only byproducts that can be easily recovered and reused for the synthesis of the same reagent, making coupling reactions to yield amides, hydroxamates, peptides, and esters more environmentally friendly and cost-effective.

see article for more examples

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Ethyl 2-Cyano-2-(4-nitrophenylsulfonyloxyimino)acetate-Mediated Lossen Rearrangement: Single-Pot Racemization-Free Synthesis of Hydroxamic Acids and Ureas from Carboxylic Acids

K. Thalluri, S. R. Manne, D. Dev, B. Mandal, J. Org. Chem., 2014, 79, 3765-3775.

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Key Words

amides, esters, hydroxamates

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ID: J42-Y2014