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Abstract <p>2-(4-Methylthiophenyl)quinazolin-4(3<i>H</i>)-one was prepared by condensation of 2-aminobenzamide with 4-methylthiobenzaldehyde in a two-step approach with isolation of the intermediate azomethine and subsequent dehydrogenation of the latter using DDQ. It was shown that the reaction of quinazolin-4(3<i>H</i>)-one with arynes, generated in situ from corresponding anthranilic acids, proceeds exclusively via an <i>S</i>-arylation pathway and leads to a series of previously unknown 2-substituted quinazolin-4(3<i>H</i>)-ones. A similar approach proved effective for the synthesis of 4-phenyl substituted 2-arylquinazolines, which expands the possibilities for modification of the quinazoline system. New quinazolines exhibit solid-state fluorescence with absolute quantum yield up to 10%, indicating their potential as functional luminescent materials.</p>

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Synthesis of Novel 2-(4-Arylthiophenyl)quinazolin-4(3H)-ones Using S-Arylation Reaction

  • 期刊论文

  • 发表日期：

    2026年2月26日

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  • Ekaterina A. Kudryashova,
  • Maria I. Valieva,
  • Yaroslav K. Shtaitz,
  • Tatyana N. Moshkina,
  • Pavel A. Slepukhin,
  • Vasily S. Gaviko,
  • Alexander S. Novikov,
  • Emiliya V. Nosova,
  • Dmitry S. Kopchuk

摘要

Abstract

2-(4-Methylthiophenyl)quinazolin-4(3H)-one was prepared by condensation of 2-aminobenzamide with 4-methylthiobenzaldehyde in a two-step approach with isolation of the intermediate azomethine and subsequent dehydrogenation of the latter using DDQ. It was shown that the reaction of quinazolin-4(3H)-one with arynes, generated in situ from corresponding anthranilic acids, proceeds exclusively via an S-arylation pathway and leads to a series of previously unknown 2-substituted quinazolin-4(3H)-ones. A similar approach proved effective for the synthesis of 4-phenyl substituted 2-arylquinazolines, which expands the possibilities for modification of the quinazoline system. New quinazolines exhibit solid-state fluorescence with absolute quantum yield up to 10%, indicating their potential as functional luminescent materials.