Amide moiety as analogue of double bond in aza-1,3,5-hexatriene system: Photochemical synthesis of benzofuro[3,2-c]isoquinolines

Amide moiety as analogue of double bond in aza-1,3,5-hexatriene system: Photochemical synthesis of benzofuro[3,2-c]isoquinolines Full article

Journal

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

Output data

Year: 2023, Volume: 141, Article number : 133497, Pages count : DOI: 10.1016/j.tet.2023.133497

Authors

Karibov Turan T. ¹ , Lichitsky Boris V. ¹ , Komogortsev Andrey N. 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

For the first time the possibility of regiospecific photocyclization of 3-amido-2-arylbenzofurans was demonstrated. Distinctive feature of the studied photoreaction is involvement of amide function as equivalent of the lateral double bond in aza-1,3,5-hexatriene system for implementation of 6π-electrocyclization. The presented type of photocyclizations is novel and has no analogs in the literature. Based on the presented results the novel approach for the synthesis of benzofuro[3,2-c]isoquinolines was elaborated. The advantages of considered method are easily available starting materials, mild reaction conditions and simple workup procedure without chromatographic purification. The structure of one of benzofuro[3,2-c]isoquinolines was proved by X-ray diffraction.

Karibov T.T. , Lichitsky B.V. , Komogortsev A.N. , Melekhina V.G.
Amide moiety as analogue of double bond in aza-1,3,5-hexatriene system: Photochemical synthesis of benzofuro[3,2-c]isoquinolines
Tetrahedron. 2023. V.141. 133497 . DOI: 10.1016/j.tet.2023.133497 WOS Scopus OpenAlex

Web of science:	WOS:001037862900001
Scopus:	2-s2.0-85163389238
OpenAlex:	W4379115067

DB	Citing
Web of science	1