General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles

General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles Full article

Journal

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

Output data

Year: 2021, Volume: 90, Article number : 132207, Pages count : DOI: 10.1016/j.tet.2021.132207

Authors

Lichitsky Boris V. ¹ , Karibov Turan T. ¹ , Melekhina Valeriya G. ¹ , Komogortsev Andrey N. ¹ , Fakhrutdinov Artem N. ¹ , Minyaev Mikhail E. ¹ , Krayushkin Michail M. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian academy of sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation

At the first time, we elaborated the method of synthesis of naphtho[1,2-b]benzofurans based on photoinduced reaction of acrylonitriles containing 2-arylbenzofuran fragment as part of 1,3,5-hexatriene system. The considered reaction proceeds via initial 6π-electrocyclization followed by [1,9]-H sigmatropic shift and final oxidative aromatization of central benzene ring. It was shown that 5,6-dihydronaphtho[1,2-b]benzofurans are key intermediates of studied process. The structures of obtained 5,6-dihydronaphtho[1,2-b]benzofuran and one of the target naphtho[1,2-b]benzofurans were confirmed by X-ray diffraction.

Lichitsky B.V. , Karibov T.T. , Melekhina V.G. , Komogortsev A.N. , Fakhrutdinov A.N. , Minyaev M.E. , Krayushkin M.M.
General approach to substituted naphtho[1,2-b]benzofurans via photochemical 6π-electrocyclization of benzofuranyl containing cinnamonitriles
Tetrahedron. 2021. V.90. 132207 . DOI: 10.1016/j.tet.2021.132207 WOS Scopus OpenAlex

Web of science:	WOS:000663120400015
Scopus:	2-s2.0-85106354748
OpenAlex:	W3162735735

DB	Citing
OpenAlex	10
Scopus	10
Web of science	11