General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile

The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 °C results in th...

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Veröffentlicht in:Tetrahedron 2012-07, Vol.68 (29), p.5833-5837
Hauptverfasser: Elinson, Michail N., Ilovaisky, Alexey I., Merkulova, Valentina M., Belyakov, Pavel A., Barba, Fructuoso, Batanero, Belen
Format: Artikel
Sprache:eng
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Zusammenfassung:The new type of non-catalytic cascade reaction was found: the direct multicomponent reaction of acenaphthenequinone, cyclic CH-acids, and malononitrile to form spiroacenaphthylene heterocycles. The direct heating in water acenaphthenequinone, cyclic CH-acids, and malononitrile at 80 °C results in the formation of spiroacenaphthylene heterocycles in 90–95% yields. Thus, a new simple and efficient green ‘one-pot’ method to synthesize substituted spiroacenaphthylene frameworks was found directly from simple starting compounds. The application of this convenient green multicomponent method is also beneficial from the viewpoint of diversity-oriented large-scale processes. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.05.005