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

Journal Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539
Output data Year: 2021, Volume: 19, Number: 45, Pages: 9975-9985 Pages count : 11 DOI: 10.1039/d1ob01871j
Authors Milyutin Constantine V. 1 , Galimova Renata D. 2,1 , Komogortsev Andrey N. 1 , Lichitskii Boris V. 1 , Melekhina Valeriya G. 1 , Migulin Vasily A. 1 , Fakhrutdinov Artem N. 1 , Minyaev Mikhail E. 1
Affiliations
1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation
2 M.V. Lomonosov Moscow State University, Leninskie Gory, 1, Moscow, 119991, Russian Federation

Abstract: A novel photochemical method for the construction of previously unknown substituted 4a,7a-dihydroxy-5-methyl-3,4,4a,7a-tetrahydro-1H-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.
Cite: Milyutin C.V. , Galimova R.D. , Komogortsev A.N. , Lichitskii B.V. , Melekhina V.G. , Migulin V.A. , Fakhrutdinov A.N. , Minyaev M.E.
Photoinduced assembly of the 3,4,4a,7a-tetrahydro-1H-cyclopenta[b]pyridine-2,7-dione core on the basis of allomaltol derivatives
Organic and Biomolecular Chemistry. 2021. V.19. N45. P.9975-9985. DOI: 10.1039/d1ob01871j WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000715914700001
Scopus: 2-s2.0-85120383841
OpenAlex: W3209671311
Citing:
DB Citing
OpenAlex 13
Scopus 12
Web of science 10
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