CuO nanoparticles: An efficient and recyclable nanocatalyst for the rapid and green synthesis of 3,4-dihydropyrano[c]chromenes

doi:10.1016/j.cclet.2011.06.003

Chinese Chemical Letters

Volume 22, Issue 12, December 2011, Pages 1419-1422

https://doi.org/10.1016/j.cclet.2011.06.003 Get rights and content

Abstract

Copper oxide nanoparticles showed excellent catalytic activity through three-component condensation reaction of aldehydes, malononitrile, and 4-hydroxycoumarin for the synthesis of 3,4-dihyropyrano[c]chromenes in water medium in excellent yields and very short reaction times.

Section snippets

Experimental

All chemicals were purchased from Aldrich and Merck with high-grade quality, and used without any purification. All melting points were obtained by Bamslead Electrothermal 9200 apparatus and are uncorrected. ¹H and ¹³C NMR spectra were recorded in DMSO-d₆ on a Bruker 500 MHz spectrometer. Infrared spectra were recorded by Bruker FT-IR Equinax-55 spectrophotometer in KBr with absorption in cm⁻¹. All products were characterized by their spectra and physical data.

Results and discussion

To find the optimal conditions, we studied synthesis of 2-amino-5-oxo-4-phenyl-4H,5H-pyrano[3,2-c]- chromene-3-carbonitrile 2a from the condensation of 4-hydroxycoumarine, benzaldehyde and malononitrile under various reaction conditions (Table 1).

We examined this reaction in the absence and presence of several nanoparticle catalysts. It was found that when the reaction was carried out without any catalysts resulted in 25% of product after 24 h (Table 1, entry 1). While good results were obtained

Conclusions

We have reported an efficient procedure through three-component coupling of aldehydes, malononitrile, and 4-hydroxycoumarin for the synthesis of 3,4-dihyropyrano[c]chromenes using CuO nanoparticles as a reusable, non-toxic and inexpensive heterogeneous nanocatalyst. The major advantage of this method is the ease of the work-up; i.e., the products can be isolated without chromatography. The method also offers some other advantages such as clean reaction, low loading of catalyst, high yields of

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CuO nanoparticles: An efficient and recyclable nanocatalyst for the rapid and green synthesis of 3,4-dihydropyrano[c]chromenes

Abstract

Section snippets

Experimental

Results and discussion

Conclusions

Eur. J. Med. Chem.

Tetrahedron Lett.

Catal. Commun.

Tetrahedron Lett.

Catal. Today

Principi Di Chemico Farmaceutica

Boll. Chim. Farm.

Chem. Abstr.

Ger. Offen DE. Chem. Abstr.

Chem. Abstr.

Pharmazie