Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes

Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes Full article

Journal

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

Output data

Year: 2010, Volume: 66, Number: 23, Pages: 4043-4048 Pages count : 6 DOI: 10.1016/j.tet.2010.04.024

Authors

Elinson Michail N. ¹ , Ilovaisky Alexey I. ¹ , Merkulova Valentina M. ¹ , Belyakov Pavel A. ¹ , Chizhov Alexander O. ¹ , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia

The new type of solvent-free cascade reaction was found: the direct heating of the mixture of salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes at 60 °C in the presence of catalytic amounts of KF or NaOAc results in the formation of 2-amino-4-(1-nitroalkyl)-4H-chromene-3-carbonitriles or methyl 2-amino-4-(1-nitroalkyl)-4H-chromene-3-carboxylates in 80–90% yields. Thus, the new simple and efficient solvent-free ‘one-pot’ way to substituted medicinally privileged 2-amino-4H-chromene scaffold was found directly from such simple and reasonable starting compounds as salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes.

Elinson M.N. , Ilovaisky A.I. , Merkulova V.M. , Belyakov P.A. , Chizhov A.O. , Nikishin G.I.
Solvent-free cascade reaction: direct multicomponent assembling of 2-amino-4H-chromene scaffold from salicylaldehyde, malononitrile or cyanoacetate and nitroalkanes
Tetrahedron. 2010. V.66. N23. P.4043-4048. DOI: 10.1016/j.tet.2010.04.024 WOS Scopus OpenAlex

Web of science:	WOS:000278198000010
Scopus:	2-s2.0-77953122591
OpenAlex:	W2122682651

DB	Citing
OpenAlex	89
Scopus	99
Web of science	97