CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
2014; Elsevier BV; Volume: 70; Issue: 34 Linguagem: Inglês
10.1016/j.tet.2014.05.059
ISSN1464-5416
AutoresJin Zhang, Decheng Ren, Yangmin Ma, Weitao Wang, Hao Wu,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoA CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement yielding quinazolin-4(3H)-ones. The catalyst is recyclable four times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance (46 quinazolinones are synthesized and 9 of them are reported firstly), and providing moderate to excellent yield of the products under mild conditions.
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