Literature DB >> 17660876

The diverse chemistry of oxazol-5-(4H)-ones.

Jason S Fisk1, Robert A Mosey, Jetze J Tepe.   

Abstract

The assembly of structurally diverse scaffolds via substrate controlled diversity oriented synthesis (DOS) has proven to be an effective tool in the discovery of novel biologically important compounds. This tutorial review aims to summarize some of the more recent applications of oxazolones as a general template for the stereoselective syntheses of amino acids and heterocyclic scaffolds. A brief introduction covers a short history, nomenclature and general reactivity of oxazolones. The main body of this tutorial review highlights several applications of oxazolones as starting blocks for the diverse and stereoselective synthesis of amino acids, oxazoles, beta-lactams, pyrroles, imidazolines, pyrrolines, and imidazoles.

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Year:  2007        PMID: 17660876     DOI: 10.1039/b511113g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  19 in total

1.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

2.  Azomethine ylide mediated inversion of configuration of quaternary imidazoline carbon: converting trans- to its cis- imidazolines.

Authors:  Ke Qu; Jason S Fisk; Jetze J Tepe
Journal:  Tetrahedron Lett       Date:  2011-09-21       Impact factor: 2.415

3.  Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids.

Authors:  Kip A Teegardin; Jimmie D Weaver
Journal:  Chem Commun (Camb)       Date:  2017-04-27       Impact factor: 6.222

4.  Benzotetramisole-catalyzed dynamic kinetic resolution of azlactones.

Authors:  Xing Yang; Guojian Lu; Vladimir B Birman
Journal:  Org Lett       Date:  2010-02-19       Impact factor: 6.005

Review 5.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

6.  NMR, mass spectrometry and chemical evidence reveal a different chemical structure for methanobactin that contains oxazolone rings.

Authors:  Lee A Behling; Scott C Hartsel; David E Lewis; Alan A DiSpirito; Dong W Choi; Larry R Masterson; Gianluigi Veglia; Warren H Gallagher
Journal:  J Am Chem Soc       Date:  2008-08-27       Impact factor: 15.419

7.  Enantioselective N-heterocyclic carbene catalyzed annulation reactions with imidazolidinones.

Authors:  Elizabeth O'Bryan McCusker; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-18       Impact factor: 15.336

8.  Enantioselective cycloaddition of münchnones onto [60]fullerene: organocatalysis versus metal catalysis.

Authors:  Juan Marco-Martínez; Silvia Reboredo; Marta Izquierdo; Vanesa Marcos; Juan Luis López; Salvatore Filippone; Nazario Martín
Journal:  J Am Chem Soc       Date:  2014-02-10       Impact factor: 15.419

9.  4-[(3-Meth-oxy-anilino)methyl-idene]-2-phenyl-1,3-oxazol-5(4H)-one.

Authors:  Wan-Yun Huang; Ye Zhang; Kun Hu; Qing-Mei Lin; Xian-Xian Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-10

10.  On the Stability and Spectroscopic Properties of 5-Hydroxyoxazole-4-carboxylic Acid Derivatives.

Authors:  Alina Tirla; Kevin M Wernke; Seth B Herzon
Journal:  Org Lett       Date:  2021-06-28       Impact factor: 6.072

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