Fully regioselective synthesis of 5-hydroxyethylpyrazoles was exploited by reacting hydrazonoyl chlorides with homopropargylic alcohols in the presence of catalytic amounts of copper(I) chloride. Good yields of pyrazolic products and mild reaction conditions were experienced notwithstanding the known, poor reactivity of homopropargylic alcohols towards hydrazonoyl chlorides. The role of copper(I) ion and some mechanistic insights for the formation of reaction products are also discussed.

Copper(I)-catalysed reaction of hydrazonyl chlorides with homopropargylic alcohols : regioselective synthesis of 5-substituted pyrazoles / G. Molteni, A. Silvani, M. Manenti. - In: SYNTHESIS. - ISSN 0039-7881. - (2022 Nov 28). [Epub ahead of print] [10.1055/s-0042-1751770]

Copper(I)-catalysed reaction of hydrazonyl chlorides with homopropargylic alcohols : regioselective synthesis of 5-substituted pyrazoles

G. Molteni
Primo
;
A. Silvani
Secondo
;
M. Manenti
Ultimo
2022

Abstract

Fully regioselective synthesis of 5-hydroxyethylpyrazoles was exploited by reacting hydrazonoyl chlorides with homopropargylic alcohols in the presence of catalytic amounts of copper(I) chloride. Good yields of pyrazolic products and mild reaction conditions were experienced notwithstanding the known, poor reactivity of homopropargylic alcohols towards hydrazonoyl chlorides. The role of copper(I) ion and some mechanistic insights for the formation of reaction products are also discussed.
hydrazonoyl chlorides; copper(I) catalysis; homopropargylic alcohols; pyrazoles; regioselective synthesis
Settore CHIM/06 - Chimica Organica
PSRL220LPRAT_01 - Piano di Sostegno alla Ricerca 2015-2017 - Linea 2 "Dotazione annuale per attività istituzionali" (anno 2020) - PRATI, LAURA - PSR_LINEA2_ / Piano di sviluppo di ricerca - Dotazioni dipartimentali - Linea 2 - 2020
28-nov-2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/947589
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