General approach to a spiro indole-3,1′-naphthalene tetracyclic system: stereoselective pseudo four-component reaction of isatins and cyclic ketones with two molecules of malononitrile

General approach to a spiro indole-3,1′-naphthalene tetracyclic system: stereoselective pseudo four-component reaction of isatins and cyclic ketones with two molecules of malononitrile Full article

Journal

RSC Advances
ISSN: 2046-2069

Output data

Year: 2015, Volume: 5, Number: 62, Pages: 50421-50424 Pages count : 4 DOI: 10.1039/c5ra03452c

Authors

Elinson M.N. ¹ , Vereshchagin A.N. ¹ , Nasybullin R.F. ¹ , Bobrovsky S.I. ¹ , Ilovaisky A.I. ¹ , Merkulova V.M. ¹ , Bushmarinov I.S. ² , Egorov M.P. ¹

Affiliations

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

A new type of catalytic stereoselective cascade pseudo four-component reaction was discovered. The simple and facile pseudo four-component reaction of isatins, cyclic ketones with two molecules of malononitrile catalyzed by triethylamine at ambient temperature stereoselectively results in the formation of tetracyclic spirooxindoles in 60–90% yields. Thus, a new simple and efficient ‘one-pot’ method to synthesize substituted spirooxindoles was found directly from reasonable starting compounds. Unique stereoselectivety was achieved on two or three centers in this pseudo four-component reaction.

Elinson M.N. , Vereshchagin A.N. , Nasybullin R.F. , Bobrovsky S.I. , Ilovaisky A.I. , Merkulova V.M. , Bushmarinov I.S. , Egorov M.P.
General approach to a spiro indole-3,1′-naphthalene tetracyclic system: stereoselective pseudo four-component reaction of isatins and cyclic ketones with two molecules of malononitrile
RSC Advances. 2015. V.5. N62. P.50421-50424. DOI: 10.1039/c5ra03452c WOS Scopus OpenAlex

Web of science:	WOS:000355987900073
Scopus:	2-s2.0-84935839042
OpenAlex:	W1914043268

DB	Citing
OpenAlex	28
Scopus	28
Web of science	25