Photoinduced 6π-Electrocyclization of 1,3,5-hexatriene system containing allomaltol fragment: A convenient approach to polycondensed pyrrole derivatives

Photoinduced 6π-Electrocyclization of 1,3,5-hexatriene system containing allomaltol fragment: A convenient approach to polycondensed pyrrole derivatives Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2022, Volume: 114, Article number : 132780, Pages count : DOI: 10.1016/j.tet.2022.132780

Authors

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

Affiliations

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

An efficient photochemical approach was developed for the synthesis of benzo[e]pyrano[3,2-g]indoles. The presented method is based on 6π-electrocyclization of terarylenes containing pyrrole and allomaltol fragments. Various options for increasing the regioselectivity of the proposed approach, including both chemical modification of the allomaltol moiety and the use of certain conditions that block side processes were suggested. Advantages of this method are the employment of readily accessible starting materials, operational simplicity and easy isolation of the target products avoiding chromatographic purification. It was demonstrated that the considered photoreaction of allomaltol derivatives can be employed for the photoacid generation. The structure of one of the synthesized photoproducts was established by X-ray diffraction.

Komogortsev A.N. , Milyutin C.V. , Lichitsky B.V. , Melekhina V.G.
Photoinduced 6π-Electrocyclization of 1,3,5-hexatriene system containing allomaltol fragment: A convenient approach to polycondensed pyrrole derivatives
Tetrahedron. 2022. V.114. 132780 . DOI: 10.1016/j.tet.2022.132780 WOS Scopus OpenAlex

Web of science:	WOS:000798569800008
Scopus:	2-s2.0-85129024063
OpenAlex:	W4223892522

DB	Citing
OpenAlex	11
Scopus	10
Web of science	12