Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1 H -cyclopenta[ b ]pyridine-2,7-dione core on the basis of allomaltol derivatives.

Autor: Milyutin CV; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Galimova RD; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru.; M.V. Lomonosov Moscow State University, Leninskie Gory, 1, Moscow, 119991, Russian Federation., Komogortsev AN; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Lichitskii BV; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Melekhina VG; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Migulin VA; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Fakhrutdinov AN; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru., Minyaev ME; N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation. dna5@mail.ru.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2021 Nov 25; Vol. 19 (45), pp. 9975-9985. Date of Electronic Publication: 2021 Nov 25.
DOI: 10.1039/d1ob01871j
Abstrakt: 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.
Databáze: MEDLINE
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