4.4 Article

Synthesis of novel pyrazoles via [2+3]-dipolar cycloaddition using alkyne surrogates

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 9, Pages 1341-1343

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.01.017

Keywords

Cycloaddition; Regioselectivity; Heterocycles; Alkyne surrogate; Dehydrohalogenation

Funding

  1. National Institutes of Health MBRS-SCORE and RCMI [3S06 GM 008047-34S1, G12RR13459]
  2. National Science Foundation NSF-RISE [HRD-0734645]
  3. National Science Foundation [MRI 0618148]
  4. W. M Keck Foundation

Ask authors/readers for more resources

The syntheses of an important class of hitherto unreported novel pyrazoles are described The regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles was achieved by the Huisgen cyclization of nitrile imines With a trisubstituted bromoalkene The substituted bromoalkene functions as an alkyne synthon which was used to construct 5,5-disubstituted bromopyrazoline intermediates that undergo aromatization to the analogous pyrazoles through the loss of HBr The cycloaddition regioselectivity was confirmed through single X-ray crystal data of one of the pyrazoles (C) 2010 Elsevier Ltd All rights reserved

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