Literature DB >> 18020351

Sequential copper-catalyzed vinylation/cyclization: an efficient synthesis of functionalized oxazoles.

Rubén Martín1, Ana Cuenca, Stephen L Buchwald.   

Abstract

A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

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Year:  2007        PMID： 18020351     DOI： 10.1021/ol7024718

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


  6 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

3.  Oxazoles for click chemistry II: synthesis of extended heterocyclic scaffolds.

Authors:  Pravin C Patil; Frederick A Luzzio; Donald R Demuth
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.

Authors:  Chi Wai Cheung; Stephen L Buchwald
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

5.  Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment.

Authors:  Jan Geldsetzer; Markus Kalesse
Journal:  Beilstein J Org Chem       Date:  2020-04-14       Impact factor: 2.883

6.  Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.

Authors:  Pierre Querard; Simon A Girard; Nick Uhlig; Chao-Jun Li
Journal:  Chem Sci       Date:  2015-10-06       Impact factor: 9.825
  6 in total

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