Synthesis of Novel 2-(4-Arylthiophenyl)quinazolin-4(3H)-ones Using S-Arylation Reaction
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.
Authors
- Emiliya V. Nosova (ORCID: https://orcid.org/0000-0002-0177-1582)
- Dmitry S. Kopchuk (ORCID: https://orcid.org/0000-0002-0397-4033)
- Tatyana N. Moshkina (ORCID: https://orcid.org/0000-0003-4131-3196)
- Мaria I. Valieva (ORCID: https://orcid.org/0000-0001-5965-1527)
- Павел А. Слепухин (ORCID: https://orcid.org/0000-0001-8132-9905)
- E. A. Kudryashova (ORCID: https://orcid.org/0000-0002-7031-5230)
- Ya. K. Shtaitz (ORCID: https://orcid.org/0000-0002-4786-5568)
- Vasily S. Gaviko
- Alexander S. Novikov
Institutions
- Peoples' Friendship University of Russia (RU)
- Ural Federal University (RU)
- St Petersburg University (RU)
- Sirius University of Science and Technology (RU)
- M.N. Mikheev Institute of Metal Physics (RU)
- Institute of Organic Synthesis (RU)
- Ural Branch of the Russian Academy of Sciences (RU)
- Ural Institute of Metals (RU)
Publication Details
- Journal
- Russian Journal of General Chemistry
- Published
- 2026-02-26
- DOI
- https://doi.org/10.1134/s1070363225606763
- Primary Topic
- Quinazolinone synthesis and applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00