Stereoselective Michael Halogenation Initiated Ring Closure (MHIRC) Synthesis of Spirocyclopropanes from Benzylidenemalononitriles and 3-Arylisoxazol-5(4H)-ones Full article
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Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096 |
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Output data | Year: 2016, Volume: 27, Number: 17, Pages: 2489-2493 Pages count : 5 DOI: 10.1055/s-0035-1562690 | ||||
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Abstract:
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.
Cite:
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
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
Identifiers:
Web of science: | WOS:000386125700016 |
Scopus: | 2-s2.0-84979202555 |
OpenAlex: | W2499538164 |