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

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

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2012, Volume: 68, Number: 29, Pages: 5833-5837 Pages count : 5 DOI: 10.1016/j.tet.2012.05.005

Authors

Elinson Michail N. ¹ , Ilovaisky Alexey I. ¹ , Merkulova Valentina M. ¹ , Belyakov Pavel A. ¹ , Barba Fructuoso ² , Batanero Belen ²

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, 119991 Moscow, Russia
2	Department of Organic Chemistry, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain

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.

Elinson M.N. , Ilovaisky A.I. , Merkulova V.M. , Belyakov P.A. , Barba F. , Batanero B.
General non-catalytic approach to spiroacenaphthylene heterocycles: multicomponent assembling of acenaphthenequinone, cyclic CH-acids and malononitrile
Tetrahedron. 2012. V.68. N29. P.5833-5837. DOI: 10.1016/j.tet.2012.05.005 WOS Scopus OpenAlex

Web of science:	WOS:000305855800018
Scopus:	2-s2.0-84862004263
OpenAlex:	W2114137329

DB	Citing
OpenAlex	47
Scopus	49
Web of science	45