Benign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction

Saeidian, Hamid; Moradnia, Farzaneh

Document Type : Original Research Article

Authors

Hamid Saeidian ¹
Farzaneh Moradnia ²

¹ Department of Science, Payame Noor University (PNU), PO Box: 19395-4697, Tehran, Iran

² Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran.

Abstract

An efficient construction of 2-(N-arylamino)benzaldehydes and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives starting from 2- hydroxybenzaldehydes has been developed. The synthesis of N-aryl-3,10-dihydroacridin-1(2H)-ones is based on the Knoevenagel condensation of dimedone to various 2-(N-arylamino)benzaldehydes, followed by an intramolecular enamination in the presence of 20 mol% of nanocrystalline ZnO. Moderate to high yields, operation simplicity, and cheap starting materials are the key features of the present method. The structures of the products were confirmed by 1H and 13C NMR spectroscopy and mass spectrometry (EI). Probable mechanisms for the present reactions to account for the formation of 2-(N-arylamino)benzaldehydes 3a-h and N-aryl-3,10-dihydroacridin-1(2H)-one derivatives 4a-h are also reported.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

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Iranian chemical communication

Benign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction

References

References

Volume 5, Issue 3, pp. 237-363, Serial No. 16
July 2017
Pages 252-261

Benign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction

References

References

Volume 5, Issue 3, pp. 237-363, Serial No. 16July 2017Pages 252-261

Volume 5, Issue 3, pp. 237-363, Serial No. 16
July 2017
Pages 252-261