Literature DB >> 16898790

A convenient synthesis of 4-alkyl-5-aminoisoxazoles.

Matthew P Bourbeau1, James T Rider.   

Abstract

[reaction: see text] A series of 4-alkyl-5-aminoisoxazoles have been synthesized in high yield by nucleophilic addition of lithiated alkyl nitriles to (alpha)-chlorooximes. The scope and limitations of this reaction were examined by varying the nature of the nitrile and chloride oxime.

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Year:  2006        PMID: 16898790     DOI: 10.1021/ol061260+

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


  8 in total

Review 1.  Recent methodologies toward the synthesis of valdecoxib: a potential 3,4-diarylisoxazolyl COX-II inhibitor.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Eur J Med Chem       Date:  2010-08-06       Impact factor: 6.514

2.  One Pot Spiropyrazoline Synthesis via Intramolecular Cyclization/Methylation.

Authors:  Sureshbabu Dadiboyena; Ashton T Hamme
Journal:  Tetrahedron Lett       Date:  2011-05-18       Impact factor: 2.415

3.  Copper-Catalyzed Alkylation of Nitroalkanes with α-Bromonitriles: Synthesis of β-Cyanonitroalkanes.

Authors:  Kirk W Shimkin; Peter G Gildner; Donald A Watson
Journal:  Org Lett       Date:  2016-02-11       Impact factor: 6.005

4.  Solid Phase Synthesis of Isoxazole and Isoxazoline-carboxamides via [2+3]-Dipolar Cycloaddition Using Resin-bound Alkynes or Alkenes.

Authors:  Sureshbabu Dadiboyena; Adel Nefzi
Journal:  Tetrahedron Lett       Date:  2012-04-18       Impact factor: 2.415

5.  Highly Potent, Chemically Stable Quorum Sensing Agonists for Vibrio Cholerae.

Authors:  Lark J Perez; Theodora K Karagounis; Amanda Hurley; Bonnie L Bassler; Martin F Semmelhack
Journal:  Chem Sci       Date:  2014-01-01       Impact factor: 9.825

6.  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

7.  Studies with beta-oxoalkanonitriles: simple novel synthesis of 3-[2,6-diaryl-4- pyridyl]-3-oxopropanenitriles.

Authors:  Sayed M Riyadh; Hamad M Al-Matar; Mohamed H Elnagdi
Journal:  Molecules       Date:  2008-12-15       Impact factor: 4.411

8.  Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles.

Authors:  Hamid Beyzaei; Mahboubeh Kamali Deljoo; Reza Aryan; Behzad Ghasemi; Mohammad Mehdi Zahedi; Mohammadreza Moghaddam-Manesh
Journal:  Chem Cent J       Date:  2018-11-15       Impact factor: 4.215

  8 in total

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