Literature DB >> 18702548

Palladium-catalyzed direct (hetero)arylation of ethyl oxazole-4-carboxylate: an efficient access to (hetero)aryloxazoles.

Cécile Verrier1, Thibaut Martin, Christophe Hoarau, Francis Marsais.   

Abstract

A straightforward route toward 2-(hetero)arylated and 2,5-di(hetero)arylated oxazoles through regiocontrolled palladium-catalyzed direct (hetero)arylation of ethyl oxazole-4-carboxylate with iodo-, bromo-, and chloro(hetero)aromatics followed by a two-step hydrolysis/decarboxylation sequence was described. The method was applied here to a neat synthesis of two 2,5-di(hetero)aryloxazole natural products, balsoxin and texaline.

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Year:  2008        PMID: 18702548     DOI: 10.1021/jo801093n

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


  8 in total

1.  Selective Janus Kinase 2 (JAK2) Pseudokinase Ligands with a Diaminotriazole Core.

Authors:  Maria-Elena Liosi; Stefan G Krimmer; Ana S Newton; Thomas K Dawson; David E Puleo; Kara J Cutrona; Yoshihisa Suzuki; Joseph Schlessinger; William L Jorgensen
Journal:  J Med Chem       Date:  2020-05-08       Impact factor: 7.446

2.  Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides.

Authors:  Enrico T Nadres; Anna Lazareva; Olafs Daugulis
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

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.  Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2012-12-07       Impact factor: 6.222

5.  Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Commun (Camb)       Date:  2014-07-31       Impact factor: 6.222

6.  Recent advances in direct C-H arylation: Methodology, selectivity and mechanism in oxazole series.

Authors:  Cécile Verrier; Pierrik Lassalas; Laure Théveau; Guy Quéguiner; François Trécourt; Francis Marsais; Christophe Hoarau
Journal:  Beilstein J Org Chem       Date:  2011-11-29       Impact factor: 2.883

7.  Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.

Authors:  Joseph Salamoun; Shelby Anderson; James C Burnett; Rick Gussio; Peter Wipf
Journal:  Org Lett       Date:  2014-03-18       Impact factor: 6.005

8.  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

  8 in total

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