Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives

Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2025, Volume: 23, Pages: 4172-4185 Pages count : 14 DOI: 10.1039/d5ob00264h

Authors

Migulin Alexander V. ¹ , Milyutin Constantine V. ¹ , Lichitsky Boris V. ¹ , Korobkov Stepan M. ² , Komogortsev Andrey N. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation
2	A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky Pr., 31-4, Moscow, 119071, Russian Federation

In the present communication, a comprehensive study of the photochemical behavior of terarylenes with a 2-aminothiazole bridge unit and an allomaltol substituent was performed. It was shown that for the considered substrates, two types of photoprocesses can be realized. By controlling the structure of the starting material, the photoprocess can be directed toward the 6π-electrocyclization of the 1,3,5-hexatriene system or the ESIPT-induced contraction of the pyranone ring. Relying on data from DFT calculations and UV-vis spectroscopy, the key features of the observed phototransformations were discussed. The investigated thiazole-containing terarylenes were utilized as a scaffold for the construction of photoacid generators (PAGs). Based on the performed research, a synthetic methodology was developed leading to series of 23 novel polycyclic photoproducts and a set of thiazole-containing salts with a quinoxaline part.

Migulin A.V. , Milyutin C.V. , Lichitsky B.V. , Korobkov S.M. , Komogortsev A.N.
Investigation of the photochemical behavior of allomaltol-containing 2-aminothiazole derivatives
Organic & Biomolecular Chemistry. 2025. V.23. P.4172-4185. DOI: 10.1039/d5ob00264h WOS Scopus OpenAlex

Web of science:	WOS:001457710400001
Scopus:	2-s2.0-105004011907
OpenAlex:	W4409118929

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