Synthesis of 3-carbonyl pyrazole-5-phosphonates via 1,3-dipolar cycloaddition of Bestmann–Ohira reagent with ynones

Abstract

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.