Literature DB >> 20449274

An improved synthesis of 1,2-benzisoxazoles: TBAF mediated 1,3-dipolar cycloaddition of nitrile oxides and benzyne.

Christian Spiteri1, Pallavi Sharma, Fengzhi Zhang, Simon J F Macdonald, Steve Keeling, John E Moses.   

Abstract

An efficient synthesis of a range of 1,2-benzisoxazoles using an improved 1,3-dipolar cycloaddition of nitrile oxides and benzyne is described. Key to the procedure is the in situ generation of the reactive nitrile oxide and benzyne reaction partners mediated by TBAF. Reactions are complete within 30 s, giving the target products in good to excellent yield.

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Year:  2010        PMID： 20449274     DOI： 10.1039/b922489k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  3 in total

1.  Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity.

Authors:  Brian C Sanders; Frédéric Friscourt; Petr A Ledin; Ngalle Eric Mbua; Selvanathan Arumugam; Jun Guo; Thomas J Boltje; Vladimir V Popik; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2010-12-23       Impact factor: 15.419

2.  Synthesis of 2H-indazoles by the [3 + 2] cycloaddition of arynes and sydnones.

Authors:  Chunrui Wu; Yuesi Fang; Richard C Larock; Feng Shi
Journal:  Org Lett       Date:  2010-05-21       Impact factor: 6.005

Review 3.  Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

Authors:  Daniel B Werz; Akkattu T Biju
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336
  3 in total

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