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February 21, 2026Journal of Heterocyclic Chemistry2 citations

Recent Advances in the Chemistry of 1,2,4‐Selenadiazole and Their Analogues

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MHMohamed H. HelalRJRasha JameMGMoustafa A. Gouda

Key Points

  • This study aims to explore the diverse synthesis methods and reactive properties of 1,2,4‐selenadiazole and its analogues.
  • Utilized oxidative dimerization of primary selenoamides with various reagents.
  • Executed in situ selenoamidation of aryl nitriles followed by oxidation.
  • Investigated selenoamidation of isocyanides with hydroxyimidamides or imidamides.
  • Applied 1,3‐dipolar cycloaddition with 1,2‐di(pyridin‐2‐yl)diselane.
  • Conducted four‐component coupling of isocyanides with 4‐substituted‐1,2‐phenylenediamines.
  • Identified multiple synthetic pathways for 1,2,4‐selenadiazole.
  • Highlighted the reactivity of selenadiazoles with various functional groups.
  • Noted the potential biological activities of 1,2,4‐selenadiazole derivatives.

Abstract

ABSTRACT A five‐membered ring incorporating two nitrogen atoms, one selenium atom, and two carbon atoms yields four distinct structural isomers: 1,2,3‐selenadiazole, 1,2,4‐selenadiazole, 1,2,5‐selenadiazole, and 1,3,4‐selenadiazole. The chemistry of selenadiazoles remains a vibrant research field due to their promising biological activities and intriguing reactivity. Synthesis of 1,2,4‐selenadiazole and its analogs can be achieved via several routes, including: (i) oxidative dimerization of primary selenoamides using reagents such as iodine, NBS, PhI(OAc) 2 , t ‐butyl nitrite, Oxone, palladium(II) salts, or α‐bromo ketones; (ii) in situ selenoamidation of aryl nitriles followed by oxidative dimerization; (iii) selenoamidation of isocyanides and subsequent cyclization with hydroxyimidamides or imidamides; (iv) 1,3‐dipolar cycloaddition of 1,2‐di(pyridin‐2‐yl)diselane with nitriles or isocyanates; (v) four‐component coupling of isocyanides with 4‐substituted‐1,2‐phenylenediamines.

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Cite This Study

Helal et al. (2026) studied this question.

synapsesocial.com/papers/69994bef873532290d020162https://doi.org/10.1002/jhet.70177
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