Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines

A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thio...

Full description

Saved in:
Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 14; no. 30; pp. 7345 - 7353
Main Authors Kim, Hee-Kwon, Lee, Anna
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Alcohols - chemistry
Amines - chemistry
Carbamates - chemical synthesis
Chemistry
Chemistry Techniques, Synthetic - methods
Chemistry, Organic
Isocyanates - chemistry
Molecular Structure
Physical Sciences
Pyridines
Science & Technology
Sulfhydryl Compounds - chemistry
Thiocarbamates - chemical synthesis
Urea - chemical synthesis
ELEMENTAL SULFUR
DIPEPTIDES
CONVERSION
HYDROLYSIS
CONVENIENT
ACETONITRILE
DERIVATIVES
PROTEASE INHIBITORS
DISCOVERY
AMIDES
Online AccessGet full text

Cover

More Information
Summary:A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01290f