| Title: |
Ethyl‐2‐Cyano‐2‐(2‐Nitrophenylsulfonyloximino)Acetate (ortho‐NosylOXY) Mediated One‐Pot Racemization Free Synthesis of Ureas, Carbamates, and Thiocarbamates via Curtius Rearrangement |
| Authors: |
Kalita, Tapasi; Dev, Dharm; Mondal, Sandip; Giri, Rajat Subhra; Mandal, Bhubaneswar |
| Contributors: |
Indian Institute of Technology Guwahati; Department of Biotechnology, Ministry of Science and Technology, India |
| Source: |
Asian Journal of Organic Chemistry ; volume 10, issue 6, page 1523-1529 ; ISSN 2193-5807 2193-5815 |
| Publisher Information: |
Wiley |
| Publication Year: |
2021 |
| Collection: |
Wiley Online Library (Open Access Articles via Crossref) |
| Description: |
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 ( o rtho‐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. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| DOI: |
10.1002/ajoc.202100198 |
| Availability: |
https://doi.org/10.1002/ajoc.202100198; https://onlinelibrary.wiley.com/doi/pdf/10.1002/ajoc.202100198; https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.202100198 |
| Rights: |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
| Accession Number: |
edsbas.FBCF69FC |
| Database: |
BASE |