Photoinduced assembly of the 3, 4, 4a, 7a-tetrahydro-1H-cyclopenta[b]pyridine-2, 7-dione core on the basis of allomaltol derivatives. Issue 45 (9th November 2021)

• Record Type: Journal Article
• Authors: Milyutin, Constantine V.; Galimova, Renata D.; Komogortsev, Andrey N.; Lichitskii, Boris V.; Melekhina, Valeriya G.; Migulin, Vasily A.; Fakhrutdinov, Artem N.; Minyaev, Mikhail E.
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 45(2021)
• Page Start: 9975
• Page End: 9985
• Publication Date: 2021-11-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01871j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel photochemical synthetic pathway to various substituted 3, 4, 4a, 7a-tetrahydro-1 H -cyclopenta[ b ]pyridine-2, 7-diones based on readily available allomaltol derivatives containing an amide group was developed. Abstract : A novel photochemical method for the construction of previously unknown substituted 4a, 7a-dihydroxy-5-methyl-3, 4, 4a, 7a-tetrahydro-1 H -cyclopenta[ b ]pyridine-2, 7-diones based on readily available allomaltol derivatives containing an amide group was established. The proposed approach includes the photoinduced contraction of an allomaltol ring and the subsequent intramolecular cyclization of an unstable α-hydroxy-1, 2-diketone intermediate. For the first time we have shown the use of a side chain amide function as a trapping element for the final cyclization of photogenerated α-hydroxy-1, 2-diketones. The structures of two synthesized photoproducts were determined by X-ray diffraction.