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Synthesis of Alkynyl Hydrazones from Unprotected Hydrazine and Their Reactivity as Diazo Precursors

Akashdeep Sharma, Paru Jamwal, Himani Vaid and Ramani Gurubrahamam*

*Department of Chemistry, Indian Institute of Technology Jammu, NH-44, PO Nagrota, Jagti, Jammu and Kashmir 181221, India, Email: guru.ramaniiitjammu.ac.in

A. Sharma, P. Jamwal, H. Vaid, R. Gurubrahamam, Org. Lett., 2023, 25, 1889-1894.

DOI: 10.1021/acs.orglett.3c00404


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Abstract

Alkynyl hydrazones can be conveniently synthesized from 2-oxo-3-butynoates and hydrazine without formation of pyrazoles. The resultant hydrazones are transformed into alkynyl diazoacetates under mild oxidative conditions in excellent yields. Further, alkynyl cyclopropane and propargyl silane carboxylates are synthesized in good yields using copper-catalyzed alkynyl carbene transfer reactions.

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Key Words

hydrazones, diazo compounds, cyclopropanes, PIDA


ID: J54-Y2023