Journal
TETRAHEDRON
Volume 70, Issue 34, Pages 5214-5220Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.05.095
Keywords
Bestmann-Ohira reagent; Dipolar cycloaddition; Ynones; Phosphonyl pyrazole
Categories
Funding
- Council of Scientific and Industrial Research, New Delhi
- CSIR-Network project (CSIR-CDRI-THUNDER) [BSC0102]
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The present work explores the hitherto unexplored reactivity of ynones as dipolarophiles with Bestmann-Ohira reagent. The reaction offers a convenient route for the synthesis of regioisomerically pure 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles in excellent yields. However, di-ynones and molecules possessing both ynone and enone functionalities provide only monocycloaddition products, whereas another multiple bond undergoes Michael addition with the methoxide anion. (C) 2014 Elsevier Ltd. All rights reserved.
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