Synthesis of Some Novel 2-Aryl-Substituted 2,3-Dihydroquinazolin-4(1H)-ones under Solvent-Free Conditions Using MCM-41-SO3H as a Highly Efficient Sulfonic Acid

Abstract

MCM-41-SO 3 H, ordered mesoporous silica material MCM-41 with covalently anchored sulfonic acid groups located inside the mesochannels, was used as an acid catalyst for the rapid and 'green' synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under solvent-free condition. This novel synthetic method offers several advantages, such as excellent yields, simple procedure, short reaction times, and mild reaction conditions.

Silica‐bonded S‐sulfonic Acid as a Recyclable Catalyst for Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones

“…All of the products are characterized by comparison of their spectral (IR, 1 H NMR), TLC and physical data with those reported in the literature. [11][12][13][14][15][16] Silica bonded S-sulfonic acid (SBSSA) was prepared according to our previously reported procedure. [19][20][21][22][23][24][25] Scheme 1 Preparation of silica-bonded S-sulfonic acid (SBSSA)…”

“…5,6 The synthesis of 2,3-dihydroquinazolinones was also achieved by reductive cyclisation of o-nitrobenzaldehyde or o-azidobenzamide. 7,8 Some of the recently reported methods include isatoic anhydride, and aldehydes with ammonium acetate or primary amine in the presence of different reagents or catalysts, namely p-toluenesulfonic acid, 9 amberlyst-15 microwaved-assisted, 10 montmorillonite K-10, 11 ionic liquid, 12 silica sulfuric acid, 13 Zn(PFO) 2 , 14 ceric ammonium nitrate, 15 and MCM-41-SO 3 H. 16 In recent years, the use of solid acidic catalysts has offered important advantages in organic synthesis, for example, operational simplicity, environmental compatibility, non-toxicity, reusability, low cost, and ease of isolation. 17,18 A tremendous upsurge of interest in various chemical transformations processes by catalysts under heterogeneous conditions has occurred.…”

Polyethylene glycol (PEG-400) as a medium for novel and efficient synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one derivatives

“…They are some marketed drugs with quinazolinone skeleton are given in Figure 1. Numerous methods have been reported for the synthesis 2,3-dihydroquinazolin-4(1H)-one derivatives by using different catalytic mediums such as KAl(SO4)2.12H2O [3], molecular iodine [4], ionic liquids ([bmim]BF4) [5], montmorillonite K-10 [6], gallium(III)triflate [7], MCM-41-SO3H [8], silica sulfuric acid [9], Al(H2PO4)3 [10], and zinc(II)perfluorooctanoate [Zn(PFO)2] [11]. Wang et al developed the aqueous phase synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and different aldehydes/ketones [12].…”

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

“…Therefore, MCRs have provided a very efficient way to access heterocycles in the past decade. So far only a few acid catalysts, e.g., p-toluenesulfonic acid [16], silica sulfuric acid [17], zinc(II) perfluorooctanoate [18], gallium(III) triflate [19], ionic liquid [20,21], Al(H 2 PO 4 ) 3 [22], I 2 [23], montmorillonite K-10 [24], Amberlyst-15 [25], Al/Al 2 O 3 and Fe 3 O 4 nanoparticles [26,27], p-toluenesulfonic acid-paraformaldehyde copolymer [28], MCM-41-SO 3 H [29], and silica-bonded N-propylsulfamic acid [30], have been reported to accomplish this threecomponent reaction. However, some of these methods have certain drawbacks such as long reaction times, low yields, use of expensive and large amounts of catalyst, and high reaction temperatures.…”