Ethyl-2-Cyano-2-(2-Nitrophenylsulfonyloximino)Acetate (ortho-NosylOXY) Mediated One-Pot Racemization Free Synthesis of Ureas, Carbamates, and Thiocarbamates via Curtius Rearrangement

Tapasi Kalita, Dharm Dev, Sandip Mondal, Rajat Subhra Giri, Bhubaneswar Mandal

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Direct conversion of carboxylic acids to ureas, carbamates, and thiocarbamates in a single pot via Curtius rearrangement is accomplished. One recently established coupling reagent, Ethyl-2-cyano-2-(2-nitrophenylsulfonyloximino)acetate (ortho-NosylOXY, I), is successfully used for the racemization free synthesis of ureas, di-peptidyl ureas, and carbamates with moderate to good yield (82–69%). This single-pot hassle-free procedure works with a diverse range of N-protecting groups Fmoc, Boc, and Cbz. Various amine, including aromatic, methyl esters of amino acids, t-butylamine, alcohols, and thiols, are used as nucleophiles. A detailed NMR-based mechanism study is incorporated here. Racemization suppression, easy removal of by-products, and less waste generation make this methodology useful.

Original languageEnglish
Pages (from-to)1523-1529
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume10
Issue number6
DOIs
StatePublished - 1 Jun 2021
Externally publishedYes

Keywords

  • Curtius rearrangement
  • carbamates
  • o-NosylOXY
  • racemization free
  • thiocarbamates
  • ureas

ASJC Scopus subject areas

  • Organic Chemistry

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