Photochemical synthesis and ring–chain–ring tautomerism of benzo[4,5]imidazo[1,2-a]cyclopenta[e]pyridines

Photochemical synthesis and ring–chain–ring tautomerism of benzo[4,5]imidazo[1,2-a]cyclopenta[e]pyridines Full article

Journal

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

Output data

Year: 2023, Volume: 21, Number: 13, Pages: 2720-2728 Pages count : 9 DOI: 10.1039/d3ob00273j

Authors

Komogortsev Andrey N. ¹ , Lichitskii Boris ¹ , Milyutin Constantine V. ¹ , Melekhina Valeriya ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation

UV-mediated approach for the preparation of benzo[4,5]imidazo[1,2-a]cyclopenta[e]pyridine derivatives from allomaltols containing a benzimidazole fragment was developed. The suggested method includes ESIPT-induced contraction of a 3-hydroxypyran-4-one core and further intramolecular trapping of unstable α-hydroxy-1,2-diketone. The distinctive feature of the obtained photoproducts is ring–chain–ring tautomerism in solution. Based on X-ray analysis, the obtained photoproducts in the solid state exist in one isomeric form. Various types of derivatization of the synthesized compounds allow both forms of tautomers to be trapped.

Komogortsev A.N. , Lichitskii B. , Milyutin C.V. , Melekhina V.
Photochemical synthesis and ring–chain–ring tautomerism of benzo[4,5]imidazo[1,2-a]cyclopenta[e]pyridines
Organic and Biomolecular Chemistry. 2023. V.21. N13. P.2720-2728. DOI: 10.1039/d3ob00273j WOS Scopus OpenAlex

Web of science:	WOS:000948276600001
Scopus:	2-s2.0-85151040871
OpenAlex:	W4323521888

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