Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines?
Organic & Biomolecular Chemistry Pub Date: 2016-07-05 DOI: 10.1039/C6OB01290F
Abstract
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.
Recommended Literature
- [1] Aggregation of biologically important peptides and proteins: inhibition or acceleration depending on protein and metal ion concentrations Benjamin Gabriel Poulson,Kacper Szczepski,Joanna Izabela Lachowicz,Lukasz Jaremko,Abdul-Hamid Emwas,Mariusz JaremkoRSC Adv., 2020,10, 215-227 10.1039/C9RA09350H
- [2] Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. BudaPhys. Chem. Chem. Phys., 2011,13, 10270-10279 10.1039/C1CP20213H
- [3] An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning? Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao DuanNanoscale, 2016,8, 19541-19550 10.1039/C6NR07585A
- [4] An approach for correlating the structural and electrical properties of Zr4+-modified SrBi4Ti4O15/SBT ceramic Priyambada Nayak,Tanmaya Badapanda,Anil Kumar Singh,Simanchalo PanigrahiRSC Adv., 2017,7, 16319-16331 10.1039/C7RA00366H
- [5] An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives? James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. HarrityChem. Commun., 2010,46, 5154-5156 10.1039/C0CC01345E
- [6] Acentric and chiral heterometallic inorganic–organic hybrid frameworks mediated by alkali or alkaline earth ions: synthesis and NLO properties Huabin Zhang,Shaowu DuCrystEngComm, 2014,16, 4059-4068 10.1039/C3CE42419G
- [7] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [8] An aqueous ammonia sensor based on an inkjet-printed polyaniline nanoparticle-modified electrode Karl Crowley,Eimer O'Malley,Aoife Morrin,Malcolm R. Smyth,Anthony J. KillardAnalyst, 2008,133, 391-399 10.1039/B716154A
- [9] An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu ChenRSC Adv., 2015,5, 100775-100782 10.1039/C5RA21508K
- [10] An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay? Suji Lee,Min Su HanChem. Commun., 2021,57, 9450-9453 10.1039/D1CC03638F
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4