One-pot synthesis of 4-(phenylselanyl)-substituted pyrazoles

ZORA M., DEMİRCİ D., KIVRAK A., Kelgokmen Y.

TETRAHEDRON LETTERS, vol.57, no.9, pp.993-997, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 9
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tetlet.2016.01.071
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.993-997
  • Keywords: Pyrazole, Selenium, Cyclization, Ferrocene, Hydrazine, Propargyl aldehyde, ELECTROPHILIC CYCLIZATION, FERROCENYL PYRAZOLES, FACILE SYNTHESIS, ORGANOSELENIUM, CHEMISTRY, FLUORINE, COMPLEX, DERIVATIVES, SILDENAFIL, TOXICOLOGY
  • Middle East Technical University Affiliated: Yes

Abstract

A facile, one-pot, general synthetic method for the preparation of 4-(phenylselanyl)pyrazoles is described. When reacted with hydrazines, alpha,beta-alkynic aldehydes produced in situ alpha,beta-alkynic hydrazones, which, upon treatment with phenylselenyl chloride, undergo cyclization to afford 4-(phenylselanyl)pyrazoles in good to high yields. This cyclization has been found to be general for a variety of in situ generated alpha,beta-alkynic hydrazones and exhibits good tolerance to a broad range of substituents, including electron-donating and electron-withdrawing groups. The enrichment of the pyrazole core with a selenyl moiety as well as with aryl and/or ferrocenyl groups may offer potential for the synthesis of molecules with pronounced or distinct biological activities. (C) 2016 Elsevier Ltd. All rights reserved.