1,4‐Conjugate Additions of Methoxyamine and 1,1‐Dimethylhydrazine to Hex‐3‐yne‐2‐one: A Facile Synthesis of Functionalized Isoxazole and Pyrazole Precursors

Abstract

When hex‐3‐yne‐2,5‐dione (2) was reacted with either methoxyamine or 1,1‐dimethylhydrazine, the 1,4‐addition products 4 and 7 were isolated in yields of 89% and 48% respectively.

Keywords:

• Michael addition
• alkynone
• oxime
• hydrazone

Acknowledgments

We are grateful to the Garden State Fellowship Commission and the J. L. R. Morgan Fellowship Fund for financial support. We thank Richard Beveridge for the ¹³C NMR spectrum.