Zeolite-Catalyzed Method for the Preparation of 2,3-Dihydroquinazolin-4(1H)-ones

Abstract

The commercial chemicals were purchased from Merck-Hungary Ltd. except E4 and E4a, which are the products of Erdőkémia-ker Ltd., Hungary. 1 H NMR spectra were recorded on a BRUKER Avanche-300 instrument using TMS as an internal standard in CDCl 3 . GC-MS spectra were made on Shimadzu GC-2010, GC-MS QP2010S instruments. Thin layer chromatography was carried out using Merck Kieselgel 60 F 254 plates with eluents hexane:acetone 4:1 or hexane:acetone 2:1, detection either by UV light at 254 nm or by heating after spraying with phosphoromolybdic acid solution. Column chromatography was carried out on Merck Kieselgel 63 -200 mesh with hexane-acetone 4:1 or 2:1 eluents.Melting points are uncorrected and were measured on Gallenkamp instrument.

2,3-Dihydroquinazolin-4(1H)-one as a privileged scaffold in drug design

“…3-substituted DHQs could be also obtained through the one-pot three-component reaction of isatoic anhydride with amines and aldehydes ( Scheme 14 ). 307–310 DHQ derivatives bearing cyclic amino substituents on N3 showed antibacterial activity, 311,312 while 3-alkylamino DHQs exhibited antimalarial effects. 313 Different heterocycles like thienyl, furyl and pyrrolidinyl in position 2 or 3-phenyl DHQs were responsible for antiviral activity, 314,315 and for the protective effect against Shiga toxin.…”

Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Catalyzed by FeCl3/Al2O3 and Analysis of Large 1 H NMR Diastereotopic Effect

“…19 Thus, an efficient synthesis of these compounds has been of great interest in past years. 20 There have been developed different methods of synthesis for 2,3-dihydroquinazolin-4(1H)-ones (DQZ) most recently; Mn III -based reaction, 21 under ultrasonic irradiation, 22 zeolite catalyzed method, 23 with green chemistry using nanoindium oxide 24 and carbon nanotubes as a heterogeneous catalyst, 25 etc. [26][27][28][29][30][31] QZ skeleton is very common in many natural alkaloids.…”