Electrocatalytic multicomponent assembling of aldehydes, dimedone and 1-naphthylamine for synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives

Poor Heravi, Mohammad Reza; Karami, Hassan; Mohammadi, Bagher; Azizkhani, Vahid

doi:10.30473/icc.2018.4162

Document Type : Original Research Article

Authors

¹ Department of Chemistry, Payame Noor University, Abhar, Iran

² Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, IRAN

https://doi.org/10.30473/icc.2018.4162

Abstract

An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction is carried out in an undivided cell containing an iron cathode and a graphite anode under a constant current density of 5 mA/cm2 (I=20 mA, electrode surface=5 cm2) in CH3CN at room temperature was found to be optimum for the electrochemically induced chain process and resulted in the highest yield.
An efficient and convenient synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives is described using the electrogenerated anion of acetonitriles as the base in the presence of tetrabutylammonium fluoride as an effective supporting electrolyte in a one-pot, three-component condensation of aromatic aldehyde, dimedone and 1-naphthyl amine. The reaction is carried out in an undivided cell containing an iron cathode and a graphite anode under a constant current density of 5 mA/cm2 (I=20 mA, electrode surface=5 cm2) in CH3CN at room temperature was found to be optimum for the electrochemically induced chain process and resulted in the highest yield.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

References

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Iranian chemical communication

Electrocatalytic multicomponent assembling of aldehydes, dimedone and 1-naphthylamine for synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives

References

References

Volume 7, Issue 2, pp. 90-159, Serial No. 23
April 2019
Pages 90-98

Electrocatalytic multicomponent assembling of aldehydes, dimedone and 1-naphthylamine for synthesis of novel tetrahydrobenzo[c]acridin-8(7H)-one derivatives

References

References

Volume 7, Issue 2, pp. 90-159, Serial No. 23April 2019Pages 90-98

Volume 7, Issue 2, pp. 90-159, Serial No. 23
April 2019
Pages 90-98