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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.

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Solid-Phase Synthesis for Constructing Thiazolotriazinone-Based Compounds Library.

Shuanghui Hua1, Jimin Moon1, Youngbeom Kim1

  • 1College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, BK21 FOUR KNU Community-Based Intelligent Novel Drug Discovery Education Unit, 80 Daehak-ro, Buk-gu, Daegu 41566, Republic of Korea.

Molecules (Basel, Switzerland)
|September 27, 2025
PubMed
Summary

Researchers developed a novel solid-phase synthesis for thiazolotriazinones. This efficient method enables rapid library construction for drug discovery and structure-activity relationship studies.

Keywords:
chemical librarymerrifield resinsolid-phase synthesisthiazolotriazinone-based compounds library

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Heterocyclic Chemistry

Background:

  • Thiazolo[4,5-d][1,2,3]triazin-4(3H)-one derivatives are important heterocyclic compounds.
  • Existing synthesis methods may lack efficiency or broad applicability.

Purpose of the Study:

  • To develop the first solid-phase synthesis of thiazolo[4,5-d][1,2,3]triazin-4(3H)-one derivatives.
  • To establish a modular and efficient protocol for library construction.

Main Methods:

  • Utilized Merrifield resin for solid-phase synthesis.
  • Employed a sequence of Thorpe-Ziegler cyclization, sulfone oxidation, and nucleophilic substitution.
  • Monitored reaction progress using real-time Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) spectroscopy.

Main Results:

  • Successfully synthesized a library of 40 thiazolotriazinone derivatives.
  • Achieved high average stepwise yields ranging from 68% to 97%.
  • Demonstrated broad functional group tolerance and mild reaction conditions.

Conclusions:

  • The developed solid-phase synthesis is efficient and versatile.
  • This protocol is suitable for constructing diverse heterocyclic libraries.
  • The method facilitates structure-activity relationship (SAR) studies for drug discovery.