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

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

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2021, Volume: 86, Number: 17, Pages: 12300-12308 Pages count : 9 DOI: 10.1021/acs.joc.1c01064

Authors

Vartanova Anna E. ^1,2 , Levina Irina I. ³ , Rybakov Victor B. ⁴ , Ivanova Olga A. ^4,2 , Trushkov Igor V. ^5,2

Affiliations

1	Faculty of Science, RUDN University, Miklukho-Maklaya 6, Moscow 117198, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow 119334, 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

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.

Vartanova A.E. , Levina I.I. , Rybakov V.B. , Ivanova O.A. , Trushkov I.V.
Donor–Acceptor Cyclopropane Ring Opening with 6-Amino-1,3-dimethyluracil and Its Use in Pyrimido[4,5-b]azepines Synthesis
Journal of Organic Chemistry. 2021. V.86. N17. P.12300-12308. DOI: 10.1021/acs.joc.1c01064 WOS Scopus OpenAlex

Web of science:	WOS:000693628600086
Scopus:	2-s2.0-85113867153
OpenAlex:	W3190587673

DB	Citing
OpenAlex	21
Scopus	19
Web of science	18