Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives and Biscoumarins

doi:10.1016/S1872-2067(11)60457-9

Chinese Journal of Catalysis ›› 2012, Vol. 33 ›› Issue (11): 1840-1849.DOI: 10.1016/S1872-2067(11)60457-9

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Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives and Biscoumarins

Khodabakhsh NIKNAM*, Abbas JAMALI

Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

Received:2012-07-31 Revised:2012-09-19 Online:2012-11-16 Published:2012-11-16

Abstract

Abstract: A simple and efficient procedure for the preparation of silica-bonded N-propylpiperazine sodium n-propionate (SBPPSP) by the hydrolysis of silica-bonded N-propylpiperazine methyl n-propionate (SBPPMP) in hydrochloric acid (0.5 mol/L) followed by treatment with saturated sodium bicarbonate is described. The SBPPMP was obtained by the reaction of 3-silica-bonded N-propylpiperazine and methyl acrylate in methanol. SBPPSP was used as a recyclable basic catalyst for the synthesis of 3,4-dihydropyrano[c]chromenes by the reaction of aromatic aldehydes, malononitrile, and 4-hydroxycoumarin in aqueous ethanol (1:1 v/v) under reflux conditions. Biscoumarins were also obtained via condensation of aldehydes and 4-hydroxycoumarin in aqueous ethanol (1:1 v/v) under reflux conditions. The catalyst could be recycled several times without any additional treatment.

Key words: silica-bonded N-propylpiperazine sodium n-propionate, silica-bonded N-propylpiperazine methyl n-propionate, aromatic aldehydes, 3,4-dihydropyrano[c]chromenes, biscoumarins

Khodabakhsh NIKNAM, Abbas JAMALI. Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives and Biscoumarins[J]. Chinese Journal of Catalysis, 2012, 33(11): 1840-1849.

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Silica-Bonded N-Propylpiperazine Sodium n-Propionate as Recyclable Basic Catalyst for Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives and Biscoumarins

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