Synthesis of Benzocarbazole Derivatives by Photocyclization. Issue 6 (17th January 2019)

• Record Type: Journal Article
• Authors: Melekhina, Valeriya G.; Mityanov, Vitaly S.; Lichitsky, Boris V.; Komogortsev, Andrey N.; Lyssenko, Konstantin A.; Krayushkin, Michail M.
• Is Part Of: European journal of organic chemistry. Issue 6(2019)
• Page Start: 1335
• Page End: 1340
• Publication Date: 2019-01-17
• Subjects: Multicomponent reactions -- Photocyclization -- Intramolecular dehydration -- Polycycles -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801664
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A simple and efficient method was developed for the synthesis of 11 H ‐benzo[ a ]carbazoles based on the photoinduced 6π‐electrocyclization of 2, 3‐disubstituted indoles. Advantages of the new method are the simplicity of implementation and the easy isolation of reaction products. The structure of one of the cyclization products was determined by X‐ray diffraction. The starting 2, 3‐disubstituted indoles were prepared by the selective three‐component condensation of aryl glyoxals with anilines and enols producing a single regioisomer. Abstract : The photoinduced cyclization of compounds containing a 1, 3, 5‐hexatriene moiety followed by elimination of a water molecule is a convenient and efficient method for the synthesis of benzocarbazoles. A simple and efficient method was developed for the synthesis of 11 H ‐benzo[ a ]carbazoles based on the photoinduced 6π‐electrocyclization of 2, 3‐disubstituted indoles.