Photoinduced 6π-Electrocyclization of a 1,3,5-Hexatriene System Containing an Allomaltol Fragment

Photoinduced 6π-Electrocyclization of a 1,3,5-Hexatriene System Containing an Allomaltol Fragment Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2021, Volume: 86, Number: 21, Pages: 15345-15356 Pages count : 12 DOI: 10.1021/acs.joc.1c01902

Authors

Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Melekhina Valeriya G. ¹ , Nasyrova Darina I. ¹ , Milyutin Constantine V. ¹

Affiliations

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

For the first time, the possibility of photocyclization of the 1,3,5-hexatriene system containing a fragment of allomaltol was demonstrated. A preparative method for the synthesis of previously unknown benzo[5,6]chromeno[8,7-d]oxazole-2,7(3H)-diones was developed based on the investigated photoreaction. A distinctive feature of this approach is the modification of the starting terarylenes aimed at blocking the competitive process leading to side reactions of the pyranone fragment. It was shown that the proposed photocyclization of substituted oxazol-2-ones can be used for the photogeneration of biologically active alcohols and various acids. The structure of one of the cyclization products was determined by X-ray diffraction.

Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G. , Nasyrova D.I. , Milyutin C.V.
Photoinduced 6π-Electrocyclization of a 1,3,5-Hexatriene System Containing an Allomaltol Fragment
Journal of Organic Chemistry. 2021. V.86. N21. P.15345-15356. DOI: 10.1021/acs.joc.1c01902 WOS Scopus OpenAlex

Web of science:	WOS:000716778300089
Scopus:	2-s2.0-85118173021
OpenAlex:	W3206548141

DB	Citing
OpenAlex	22
Scopus	21
Web of science	21