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

Gelson Perin; Patrick C. Nobre; Daniela H. Mailahn; Márcio S. Silva; Thiago Barcellos; Raquel G. Jacob; Eder J. Lenardão; Claudio Santi; Juliano A. Roehrs

doi:10.1055/s-0037-1611747

Synthesis, Table of Contents

Synthesis 2019; 51(11): 2293-2304
DOI: 10.1055/s-0037-1611747

paper

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

Gelson Perin *

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Patrick C. Nobre

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Daniela H. Mailahn

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Márcio S. Silva

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Thiago Barcellos

^bLaboratório de Biotecnologia de Produtos Naturais e Sintéticos, Universidade de Caxias do Sul – UCS, Caxias do Sul, RS, Brazil

,

Raquel G. Jacob

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Eder J. Lenardão

^aLaboratório de Síntese Orgânica Limpa – LASOL, CCQFA, Universidade Federal de Pelotas – UFPel, P. O. Box 354, 96010-900, Pelotas, RS, Brazil Email: gelson_perin@ufpel.edu.br

,

Claudio Santi

^cDepartment of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, Perugia, Italy

,

Juliano A. Roehrs

^dInstituto Federal de Educação Ciência e Tecnologia Sul-rio-grandense, IFSul, 96015360, Pelotas, RS, Brazil

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Abstract

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Abstract

A simple and efficient method for the synthesis of 4‑organoselanyl-1H-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 ⁷⁷Se NMR spectroscopy and high-resolution mass spectrometry (HRMS).

Key words

selenium - Oxone^® - 1H-pyrazoles - cyclizations - alkynes - hydrazones

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References

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