Donor-Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5- b]azepines Synthesis

A scandium trifluoromethanesulfonate-catalyzed reaction of donor-acceptor cyclopropanes with 6-amino-1,3-dimethyluracil was found to proceed as three-membered ring opening via nucleophilic attack of the C(5) atom of an ambident nucleophile serving as an enamine equivalent. It was shown that, under basic conditions, the obtained products underwent cyclization to 6,7-dihydro-1H-pyrimido[4,5-b]azepine-2,4,8-triones, an interesting subclass of nucleobase analogues. © 2021 American Chemical Society.

Authors
Vartanova A.E. 1, 2 , Levina I.I.3 , Rybakov V.B. 4 , Ivanova O.A. 1, 4 , Trushkov I.V. 1, 5
Journal
Journal of Organic Chemistry
Number of issue
17
Language
English
Pages
12300-12308
Status
Published
Link
External link
DOI
10.1021/acs.joc.1c01064
Volume
86
Year
2021
Organizations
  • 1 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119334, Russian Federation
  • 2 Faculty of Science, RUDN University, Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
  • 3 N. M. Emanuel Institute of Biochemical Physics Russian Academy of Sciences, Kosygina 4, Moscow, 119334, Russian Federation
  • 4 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russian Federation
  • 5 Laboratory of Chemical Synthesis, Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow, 117997, Russian Federation
Keywords
Chemistry; Organic compounds; Azepines; Basic conditions; Catalyzed reactions; Donor-acceptor cyclopropanes; Nucleobases; Nucleophilic attack; Three-membered rings; Trifluoromethanesulfonate; Propane
Date of creation
16.12.2021
Date of change
16.12.2021
Short link
https://repository.rudn.ru/en/records/article/record/76620/
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