Literature DB >> 23526841

Improved synthesis of 3-aryl isoxazoles containing fused aromatic rings.

Yousef R Mirzaei1, Matthew J Weaver, Scott A Steiger, Alison K Kearns, Mariusz P Gajewski, Kevin C Rider, Howard D Beall, N R Natale.   

Abstract

A critical comparison of methods to prepare sterically hindered 3-aryl isoxazoles containing fused aromatic rings using the nitrile oxide cycloaddition (NOC) reveal that modification of the method of Bode, Hachisu, Matsuura, and Suzuki (BHMS), utilizing either triethylamine as base or sodium enolates of the diketone, ketoester, and ketoamide dipolarophiles, respectively, was the method of choice for this transformation.

Entities:  

Year:  2012        PMID： 23526841      PMCID： PMC3601750          DOI： 10.1016/j.tet.2012.09.084

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  16 in total

1.  Minimally invasive lymphatic mapping using fluorescently labeled vitamin B12.

Authors:  James M McGreevy; Michelle J Cannon; Charles B Grissom
Journal:  J Surg Res       Date:  2003-05-01       Impact factor: 2.192

2.  Orthogonally protected thiazole and isoxazole diamino acids: an efficient synthetic route.

Authors:  Jeffrey D Butler; Keith C Coffman; Kristin T Ziebart; Michael D Toney; Mark J Kurth
Journal:  Chemistry       Date:  2010-08-09       Impact factor: 5.236

3.  Bis-anthracenyl isoxazolyl amides have enhanced anticancer activity.

Authors:  Mariusz P Gajewski; Howard Beall; Mark Schnieder; Sarah M Stranahan; Michael D Mosher; Kevin C Rider; Nicholas R Natale
Journal:  Bioorg Med Chem Lett       Date:  2009-06-13       Impact factor: 2.823

4.  Synthesis and structure-activity relationships of isoxazole carboxamides as growth hormone secretagogue receptor antagonists.

Authors:  Zhili Xin; Hongyu Zhao; Michael D Serby; Bo Liu; Verlyn G Schaefer; Douglas H Falls; Wiweka Kaszubska; Christine A Colins; Hing L Sham; Gang Liu
Journal:  Bioorg Med Chem Lett       Date:  2005-02-15       Impact factor: 2.823

5.  Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

Authors:  Jeffrey W Bode; Yoshifumi Hachisu; Tomoo Matsuura; Keisuke Suzuki
Journal:  Org Lett       Date:  2003-02-20       Impact factor: 6.005

6.  Parallel Synthesis of bis-heterocyclic isoxazolylmethyl- and isoxazolinylmethylpyrazoles.

Authors:  Liping Meng; Beth A Lorsbach; Thomas C Sparks; James C Fettinger; Mark J Kurth
Journal:  J Comb Chem       Date:  2010 Jan-Feb

7.  Versatile "traceless" sulfone linker for SPOS: preparation of isoxazolinopyrrole 2-carboxylates.

Authors:  Sung Hee Hwang; Mark J Kurth
Journal:  J Org Chem       Date:  2002-09-06       Impact factor: 4.354

8.  Isoxazolopyrimidines as Novel ΔF508-CFTR Correctors.

Authors:  Gui Jun Yu; Baoxue Yang; A S Verkman; Mark J Kurth
Journal:  Synlett       Date:  2010-04-01       Impact factor: 2.454

9.  Design, synthesis and biological evaluation of a novel class of anticancer agents: anthracenylisoxazole lexitropsin conjugates.

Authors:  Xiaochun Han; Chun Li; Michael D Mosher; Kevin C Rider; Peiwen Zhou; Ronald L Crawford; William Fusco; Andrzej Paszczynski; Nicholas R Natale
Journal:  Bioorg Med Chem       Date:  2008-12-31       Impact factor: 3.641

10.  Solid-phase synthesis of 5-isoxazol-4-yl-[1,2,4]oxadiazoles.

Authors:  Chao Quan; Mark Kurth
Journal:  J Org Chem       Date:  2004-03-05       Impact factor: 4.354
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  4 in total

1.  AIMing towards improved antitumor efficacy.

Authors:  Matthew J Weaver; Alison K Kearns; Sascha Stump; Chun Li; Mariusz P Gajewski; Kevin C Rider; Donald S Backos; Philip R Reigan; Howard D Beall; Nicholas R Natale
Journal:  Bioorg Med Chem Lett       Date:  2015-03-03       Impact factor: 2.823

2.  Ethyl 3-(9-chloro-10-oxo-9,10-di-hydro-anthracen-9-yl)-5-methyl-isoxazole-4-carboxyl-ate.

Authors:  Nathan S Duncan; Howard D Beall; Alison K Kearns; Chun Li; Nicholas R Natale
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-19

3.  Ethyl 3-(10-bromo-anthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxyl-ate.

Authors:  Chun Li; Michael J Campbell; Matthew J Weaver; Nathan S Duncan; Janet L Hunting; Nicholas R Natale
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-11-23

4.  Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides.

Authors:  Md Imran Hossain; Md Imdadul H Khan; Seong Jong Kim; Hoang V Le
Journal:  Beilstein J Org Chem       Date:  2022-04-22       Impact factor: 2.544
  4 in total

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