Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes

Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes Full article

Journal

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

Output data

Year: 2020, Volume: 18, Number: 16, Pages: 3098-3103 Pages count : 6 DOI: 10.1039/d0ob00296h

Authors

Zakharov A.V. ¹ , Yadykov A.V. ¹ , Lvov A.G. ¹ , Mitina E.A. ¹ , Shirinian V.Z. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia

A novel protocol for the synthesis of functionalized phenanthrenes through photocyclization of diarylethenes (DAE) under UV irradiation is proposed. The reaction proceeds through 6π-electrocyclization with the formation of a cyclic (closed) intermediate that undergoes a rearrangement affording unsymmetrical phenanthrenes in good yields. However, in contrast to benzene derivatives, the photocyclization of naphthalene diarylethenes proceeds more slowly, which is confirmed by DFT calculations. The transformation was performed on a 1 mmol scale. The scalability showed that the diarylethenes bearing oxazole, thiazole, pyrazole and imidazole as aryl moieties are more prone to photorearrangement and can be used in preparative organic synthesis.

Zakharov A.V. , Yadykov A.V. , Lvov A.G. , Mitina E.A. , Shirinian V.Z.
Photochemical rearrangement of diarylethenes: synthesis of functionalized phenanthrenes
Organic & Biomolecular Chemistry. 2020. V.18. N16. P.3098-3103. DOI: 10.1039/d0ob00296h WOS Scopus OpenAlex

Web of science:	WOS:000531337600013
Scopus:	2-s2.0-85084167361
OpenAlex:	W3013949632

DB	Citing
OpenAlex	19
Scopus	19
Web of science	18