Literature DB >> 16095326

Practical synthesis of unsymmetrical ureas from isopropenyl carbamates.

Isabelle Gallou1, Magnus Eriksson, Xingzhong Zeng, Chris Senanayake, Vittorio Farina.   

Abstract

A very convenient method for the synthesis of unsymmetrical ureas is described, based on isopropenyl carbamates. The synthetic efficiency of traditional methods for urea formation, such as use of phosgene or alkyl and aryl carbamates, is limited by the formation of symmetrical urea side products or reaction reversibility. Isopropenyl carbamates react with amines cleanly and irreversibly and give unsymmetrical ureas in high yield and purity. This method is ideal for the rapid synthesis of compound libraries.

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Year:  2005        PMID: 16095326     DOI: 10.1021/jo0507643

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Detailed Analysis for the Solvolysis of Isopropenyl Chloroformate.

Authors:  Malcolm John D'Souza; Kevin Edward Shuman; Arnold Ochieng Omondi; Dennis Neil Kevill
Journal:  Eur J Chem       Date:  2011-06

2.  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

3.  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

4.  Urea Derivatives in Modern Drug Discovery and Medicinal Chemistry.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  J Med Chem       Date:  2019-12-02       Impact factor: 7.446

5.  Living Polymerization of 2-Ethylthio-2-oxazoline and Postpolymerization Diversification.

Authors:  You-Chi Mason Wu; Timothy M Swager
Journal:  J Am Chem Soc       Date:  2019-07-31       Impact factor: 15.419

  5 in total

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