Synthesis of 1‐Substituted Pyrazolines by Reaction of Donor‐Acceptor Cyclopropanes with 1,5‐Diazabicyclo[3.1.0]hexanes

Synthesis of 1‐Substituted Pyrazolines by Reaction of Donor‐Acceptor Cyclopropanes with 1,5‐Diazabicyclo[3.1.0]hexanes Научная публикация

Журнал

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Вых. Данные

Год: 2019, Том: 2019, Номер: 31-32, Страницы: 5475-5485 Страниц : 11 DOI: 10.1002/ejoc.201900579

Авторы

Chagarovskiy Alexey O. ^1,2 , Kuznetsov Vladimir V. ² , Ivanova Olga A. ^2,3 , Goloveshkin Alexander S. ⁴ , Levina Irina I. ⁵ , Makhova Nina N. ² , Trushkov Igor V. ^1,2

Организации

1	Oncology and Immunology, Dmitry Rogachev National Research Center of Pediatric Hematology, 117997 Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry of Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
3	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1–3, Moscow 119991, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova 28, 119991 Moscow, Russian Federation
5	N. M. Emanuel Institute of Biochemical Physics Russian Academy of Sciences, Kosygina 4, Moscow 119334, Russian Federation

Substituted pyrazolines were obtained by Ni(ClO4)2·6H2O-catalyzed reaction of 1,5-diazabicyclo[3.1.0]hexanes with donor-acceptor cyclopropanes. The mechanism of this reaction includes alkylation of diaziridine nitrogen with Lewis acid-activated donor-acceptor cyclopropane followed by hydration of the formed 1,6-zwitterionic intermediate and oxidation of pyrazolidine with air oxygen. This pathway is realized when starting bicyclic diaziridines have bulky alkyl substituent(s) at the C(6) atom preventing (3+3)-annulation of two three-membered rings.

Chagarovskiy A.O. , Kuznetsov V.V. , Ivanova O.A. , Goloveshkin A.S. , Levina I.I. , Makhova N.N. , Trushkov I.V.
Synthesis of 1‐Substituted Pyrazolines by Reaction of Donor‐Acceptor Cyclopropanes with 1,5‐Diazabicyclo[3.1.0]hexanes
European Journal of Organic Chemistry. 2019. V.2019. N31-32. P.5475-5485. DOI: 10.1002/ejoc.201900579 WOS Scopus OpenAlex

Web of science:	WOS:000483709700051
Scopus:	2-s2.0-85067542813
OpenAlex:	W2945202310

БД	Цитирований
OpenAlex	21
Scopus	20
Web of science	20