Eco‐friendly and Efficient Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones

Abstract

A simple and facile method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the direct cyclocondensation of one-pot three-component cyclocondensation of isatoic anhydride, ammonium acetate (or primary amines) and aldehydes; and anthranilamide and aldehydes using silica supported ferric chloride (SiO 2 -FeCl 3 ) as catalyst under solvent-free conditions is described.

In situfabrication of HDA-mediated NiFe–Fe2O3nanorods: an efficient and recyclable heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water

“…On the basis of the aforementioned control experiments and previous reports, 17,28,56 a reasonable reaction mechanism is proposed (Scheme 2). The reaction was initiated by the interaction of the catalyst and carbonyl oxygen of isatoic anhydride.…”

“…On the basis of the aforementioned control experiments and previous reports, 17,28,56 a reasonable reaction mechanism is attack of amide nitrogen takes place on the electrophilic imine carbon, followed by a 1,5-proton shift, affording the final 2,3dihydroquinazolin-4(1H)-one compound.…”

“…Due to these loopholes, the latter has gained significant attention among the research community in the last few decades. To date, a large number of heterogeneous catalysts such as SiO 2 -FeCl 3 , 17 metal-MWCNTs nanocomposites, 18 CoFe 2 O 4 @B 2 O 3 -SiO 2 , 19 silica sulfuric acid, 20 TiO 2 nanoparticles, 21 ZnO nanoparticles, 22 CuO nanoparticles, 23 Amberlyst-15, 24 Cu-CNTs, 25 MCM-41-SO 3 H, 26 [bmim]BF 4 , 27 and [PyPS] 3 PW 12 O 40 28 have been employed to accomplish this MCR strategy. However, these methodologies involve at least one of the following shortcomings such as environmentally harmful solvent, expensive catalysts, tedious process for the preparation of catalysts, high metal loading, long reaction periods, and high temperature.…”

Sustainable parts‐per‐million level catalysis with FeIII: One‐pot cascade synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones in water

“…[23][24][25] In this particular MCR mentioned above, there were a few methods reported in literature, which used iron as homogeneous and heterogeneous catalysts in different solvent media. [26][27][28] Because the exploration of iron catalyst in this particular reaction is very less, the development of new iron catalysed strategy with extremely low metal content is of noteworthy interest. One of the naturally occurring minerals, silica has been employed in many industrial processes.…”

An efficient synthesis of 3-benzylquinazolin-4(1H)-one derivatives under catalyst-free and solvent-free conditions

“…Therefore, simpler and high yield approach toward this valuable nucleus is much desirable. In addition, in reported papers, ammonia water (5, 16Á18), ammonium salt (5Á9, 19), and aromatic amine (6,15) were often used to synthesize quinazolin-4(1H)-one derivative, but benzylamine *Corresponding author. Email: lcrong2005@yahoo.com was seldom used in this synthesis.…”