Literature DB >> 16737297

Suzuki coupling of oxazoles.

Emmanuel Ferrer Flegeau1, Matthew E Popkin, Michael F Greaney.   

Abstract

A protocol for the functionalization of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2-Aryl-4-trifloyloxazoles undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo- and heterodimeric 4,4-linked dioxazoles. [reaction: see text]

Entities:  

Year:  2006        PMID: 16737297     DOI: 10.1021/ol060591j

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


  6 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  Condensation reactions to form oxazoline-substituted potassium organotrifluoroborates.

Authors:  Gary A Molander; Wilma Febo-Ayala; Ludivine Jean-Gérard
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

3.  Synthesis of Substituted 2-phenylhistamines via a Microwave Promoted Suzuki Coupling.

Authors:  Amanda P Skoumbourdis; Susanna Moore; Marc Landsman; Craig J Thomas
Journal:  Tetrahedron Lett       Date:  2007-12-24       Impact factor: 2.415

4.  Discovery of MK-4409, a Novel Oxazole FAAH Inhibitor for the Treatment of Inflammatory and Neuropathic Pain.

Authors:  Harry R Chobanian; Yan Guo; Ping Liu; Marc D Chioda; Selena Fung; Thomas J Lanza; Linda Chang; Raman K Bakshi; James P Dellureficio; Qingmei Hong; Mark McLaughlin; Kevin M Belyk; Shane W Krska; Amanda K Makarewicz; Elliot J Martel; Joseph F Leone; Lisa Frey; Bindhu Karanam; Maria Madeira; Raul Alvaro; Joyce Shuman; Gino Salituro; Jenna L Terebetski; Nina Jochnowitz; Shruti Mistry; Erin McGowan; Richard Hajdu; Mark Rosenbach; Catherine Abbadie; Jessica P Alexander; Lin-Lin Shiao; Kathleen M Sullivan; Ravi P Nargund; Matthew J Wyvratt; Linus S Lin; Robert J DeVita
Journal:  ACS Med Chem Lett       Date:  2014-04-10       Impact factor: 4.345

5.  Silver Benzoate Facilitates the Copper-Catalyzed C-N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles.

Authors:  Cedric Lozano; Cristian Ramirez; Ny Sin; Hélène M-F Viart; Stanley B Prusiner; Nick A Paras; Jay Conrad
Journal:  ACS Omega       Date:  2021-03-31

6.  A convenient catalyst system for microwave accelerated cross-coupling of a range of aryl boronic acids with aryl chlorides.

Authors:  Matthew L Clarke; Marcia B France; Jose A Fuentes; Edward J Milton; Geoffrey J Roff
Journal:  Beilstein J Org Chem       Date:  2007-05-30       Impact factor: 2.883

  6 in total

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