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

- فلوچارت مراحل ورود و ثبت نام در سامانه نشریات علمی وزارت عتف

- راه اندازی سیستم مدیریت نشریات علمی دانشگاه پیام نور

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	Benign synthesis of N-aryl-3,10-dihydroacridin-1(2H)-one derivatives via ZnO nanoparticle-catalyzed Knoevenagel condensation/intramolecular enamination reaction
Iranian chemical communication
مقاله 3، دوره 5، Issue 3, pp. 237-363, Serial No. 16، مهر 2017، صفحه 252-261 اصل مقاله (809.87 K)
نوع مقاله: Original Research Article
نویسندگان
Hamid Saeidian^* ¹؛ Farzaneh Moradnia²
¹Department of Science, Payame Noor University (PNU), PO Box: 19395-4697, Tehran, Iran
²Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran.
چکیده
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.
کلیدواژه‌ها
N-aryl-3,10-dihydroacridin-1(2H)-ones؛ 2-(N-arylamino)benzaldehydes؛ ZnO nanoparticles؛ smiles rearrangement

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