Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones

Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones Научная публикация

Журнал

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Вых. Данные

Год: 2016, Том: 27, Номер: 17, Страницы: 2489-2493 Страниц : 5 DOI: 10.1055/s-0035-1562690

Авторы

Vereshchagin Anatoly N. ¹ , Elinson Michail N. ¹ , Korshunov Alexander D. ¹ , Anisina Yuliya E. ¹ , Novikov Roman A. ¹ , Goloveshkin Alexander S. ² , Bushmarinov Ivan S. ² , Zlotin Sergey G. ¹ , Egorov Mikhail P. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow, 119991, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova str. 28, Moscow, 119991, Russian Federation

The new chemical cascade reaction was found: the direct formation of substituted 4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles from benzylidenemalononitriles and 3-aryl-2-isoxazol-5(4H)-ones. The action of bromine on the equimolar mixture of benzylidenemalononitrile and 3-aryl-2-isoxazol-5(4H)-one in the basic alcohol solution results in stereoselective formation of spirobicycle containing the 2-isoxazolin-5-one and the cyclopropane fragments in 53–92% yields. Thus, the new simple and efficient ‘one-pot’ approach to substituted (2R*,3R*)-4-oxo-2,7-diaryl-5-oxa-6-azaspiro[2.4]hept-6-ene-1,1-dicarbonitriles was found directly from simple and reasonable starting compounds as benzylidenemalonitriles and 3-aryl-2-isoxazol-5(4H)-ones.

Vereshchagin A.N. , Elinson M.N. , Korshunov A.D. , Anisina Y.E. , Novikov R.A. , Goloveshkin A.S. , Bushmarinov I.S. , Zlotin S.G. , Egorov M.P.
Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones
Synlett. 2016. V.27. N17. P.2489-2493. DOI: 10.1055/s-0035-1562690 WOS Scopus OpenAlex

Web of science:	WOS:000386125700016
Scopus:	2-s2.0-84979202555
OpenAlex:	W2499538164

БД	Цитирований
OpenAlex	9
Scopus	13
Web of science	13