Literature DB >> 19908883

Carbonyldiimidazole-mediated Lossen rearrangement.

Pascal Dubé1, Noah F Fine Nathel, Michael Vetelino, Michel Couturier, Claude Larrivée Aboussafy, Simon Pichette, Matthew L Jorgensen, Mark Hardink.   

Abstract

Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO(2) being the sole stoichiometric byproduct. Significant for large-scale application, the method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19908883     DOI： 10.1021/ol9023387

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  18 in total

1.  Detoxifying carcinogenic polyhalogenated quinones by hydroxamic acids via an unusual double Lossen rearrangement mechanism.

Authors:  Ben-Zhan Zhu; Jun-Ge Zhu; Li Mao; Balaraman Kalyanaraman; Guo-Qiang Shan
Journal:  Proc Natl Acad Sci U S A       Date:  2010-11-12       Impact factor: 11.205

2.  Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

3.  Targeting botulinum A cellular toxicity: a prodrug approach.

Authors:  Peter Silhár; Lisa M Eubanks; Hajime Seki; Sabine Pellett; Sacha Javor; William H Tepp; Eric A Johnson; Kim D Janda
Journal:  J Med Chem       Date:  2013-10-15       Impact factor: 7.446

4.  Synthesis of unsymmetrical diarylureas via Pd-catalyzed C-N cross-coupling reactions.

Authors:  Simon Breitler; Nathan J Oldenhuis; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

5.  Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors:  Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

6.  Synthesis of Azolo[1,3,5]triazines via Rhodium(III)-Catalyzed Annulation of N-Azolo Imines and Dioxazolones.

Authors:  Gia L Hoang; Kim Søholm Halskov; Jonathan A Ellman
Journal:  J Org Chem       Date:  2018-06-27       Impact factor: 4.354

7.  Preparation and biological evaluation of synthetic and polymer-encapsulated congeners of the antitumor agent pactamycin: insight into functional group effects and biological activity.

Authors:  Robert J Sharpe; Justin T Malinowski; Federico Sorana; J Christopher Luft; Charles J Bowerman; Joseph M DeSimone; Jeffrey S Johnson
Journal:  Bioorg Med Chem       Date:  2015-02-21       Impact factor: 3.641

8.  N-Methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the Lossen rearrangement.

Authors:  Sabesan Yoganathan; Scott J Miller
Journal:  Org Lett       Date:  2013-01-17       Impact factor: 6.005

9.  Palladium-catalyzed synthesis of N-aryl carbamates.

Authors:  Ekaterina V Vinogradova; Nathaniel H Park; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-02-26       Impact factor: 6.005

10.  Synthesis/biological evaluation of hydroxamic acids and their prodrugs as inhibitors for Botulinum neurotoxin A light chain.

Authors:  Hajime Seki; Sabine Pellett; Peter Silhár; G Neil Stowe; Beatriz Blanco; Matthew A Lardy; Eric A Johnson; Kim D Janda
Journal:  Bioorg Med Chem       Date:  2013-12-08       Impact factor: 3.641
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.