Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using copper benzenesulfonate as a reusable catalyst in aqueous solution

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

“…Catalysts bearing sulfonic acid functionalities were also widely used in the multi-component reactions. [61][62][63][64][65][66] They signicantly reduced the reaction time, generating DHQs with 50-98% yield. Recently, the use of N-halo sulfonamides as catalysts, broadly reported in organic synthesis, has been attempted in the one-pot three-component reaction.…”

“…Some Lewis acid catalysts had the advantage of being easily recovered aer the reaction and recycled several times without considerable loss of reactivity. 63,64,66,71 b-Cyclodextrin (b-CD) is a cyclic oligosaccharide, composed of seven glucose units connected "head-to-tail" by 1,4-links. This cyclic heptamer has a truncated cone shape, with a hydrophobic cavity in the center.…”

Preparation and characterization of a silica‐based magnetic nanocomposite and its application as a recoverable catalyst for the one‐pot multicomponent synthesis of quinazolinone derivatives

“…Quinazoline derivatives are an important class of heterocyclic compounds that have diverse biological and pharmaceutical properties such as antifertility, antibacterial, antiviral, antitumor and antifungal activities . Quinazolin‐4(3 H )‐one analogues as important pharmacologically active compounds have been synthesized using several methods . The most common procedure involves the condensation reaction of anthranilamide with aldehydes or ketones using various catalysts such as TiCl 4 –Zn, Sc(OTf) 3 , NH 4 Cl, HCl, p ‐toluenesulfonic acid (PTSA), SmI 2 , CuCl 2 , MnO 2 , KMnO 4 , ionic liquid or 2,2,2‐trifluoroethanol without additional catalyst and copper‐catalysed Ullmann N ‐arylation coupling process …”

“…Several strategies for the synthesis of 2,3‐dihydroquinazolinone derivatives involve a one‐pot three‐component condensation of isatoic anhydride, aldehydes and amines or ammonium acetate using catalysts such as Ga(OTf) 3 , Bi(NO 3 ) 3 ⋅5H 2 O, KAl(SO 4 ) 2 ⋅12H 2 O, PTSA, Fe 3 O 4 , SrCl 2 ⋅6H 2 O and Cu(C 6 H 5 SO 3 ) 2 ⋅6H 2 O …”

Incredible Role of Glycerol in Multicomponent Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones and 1-Amidoalkyl-2-naphthols

“…Therefore various procedures have been developed for preparing this important class of compounds. 19 Other methods including synthesis of 2,3-dihydroquinazoline 4(1H)-ones via one-pot threecomponent reaction catalyzed by L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate (supported on silica gel), 20 Cu-CNTs, 21 copper-catalyzed, 22 Ce(CH3SO3)3 • 2H2O, 23 montmorillonite K-10, 24 MCM-41-SO3H, 25 gallium triflate, 26 were also reported. However, most of the synthetic protocols reported so far suffer from drawbacks such as low yields, long reaction times, the use of expensive or toxic metal salts as catalysts, the use of toxic solvents and tedious work-up procedures.…”