Synthesis of 4-Organoselanyl-1H-pyrazoles: Oxone®-Mediated Electrophilic Cyclization of α,β-Alkynyl Hydrazones by Using Diorganyl Diselenides

Abstract A simple and efficient method for the synthesis of 4‑organoselanyl-1 H -pyrazoles has been developed, taking place under metal- and halogen-free conditions. Electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone ® in ethanol as so...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2019-06, Vol.51 (11), p.2293-2304
Main Authors: Perin, Gelson, Nobre, Patrick C., Mailahn, Daniela H., Silva, Márcio S., Barcellos, Thiago, Jacob, Raquel G., Lenardão, Eder J., Santi, Claudio, Roehrs, Juliano A.
Format: Article
Language:English
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Abstract A simple and efficient method for the synthesis of 4‑organoselanyl-1 H -pyrazoles has been developed, taking place under metal- and halogen-free conditions. Electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone ® in ethanol as solvent in an open-flask at 70 °C. These electrophilic selenium species were employed in the selenylation/cyclization of α,β-alkynyl hydrazones, giving the title compounds in moderate to excellent yields. The final species of selenium obtained from the reaction of diphenyl diselenide with Oxone ® were characterized by 77 Se NMR spectroscopy and high-resolution mass spectrometry (HRMS).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1611747