Pentafluorophenylammonium triflate-CuCl2: A mild, efficient and reusable heterogeneous catalyst system for facile synthesis of 4(3H)-quinazolinones under solvent-free conditions

Abstract

Pentafluorophenylammonium triflate (PFPAT) was found to be highly efficient, and recyclable heterogeneous catalyst for the synthesis of 4(3H)-quinazolinones by cyclocondensation reaction of 2aminobenzamide with aryl aldehydes in the presence of CuCl 2 as co-catalyst in good to excellent yields under solvent-free conditions. The present methodology offers several advantages, such as simple procedure with an easy work-up, high yields, short reaction times, and the absence of any volatile or hazardous organic solvents. Moreover, the catalyst can be easily recovered and reused at least three times with only slight reduction in its catalytic activity.

Csp2–O and C–C Bond Formation via Pd‐Catalyzed Coupling Reaction of 2,4‐Dichloroquinazoline

“…This compound was obtained as light yellow‐colored solid (ethanol); mp 238–240°C (Lit. mp 251–253°C); 154 mg, 64% yield; IR (KBr, cm −1 ) ν: 3350, 3044, 1660, 1286, 1164; 1 H NMR (400 MHz, CDCl 3 ): δ 10.62 (1H, s, NH), 8.33–8.31 (1H, d, J = 7.76 Hz), 8.20–8.16 (2H, m), 7.83–7.82 (2H, d, J = 3.28 Hz), 7.54–7.50 (1H, m), 7.27–7.26 (2H, d, J = 5.04 Hz); 13 C NMR (100 MHz, CDCl 3 ): δ 163.3, 162.4, 150.5, 149.4, 135.1, 131.8, 129.5, 129.4, 128.1, 127.1, 126.5, 126.3, 120.8, 116.5, 116.3; MS‐ESI, m / z : 241.1 (M + 1) + .…”

Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview

“…A variety of conditions in the absence of a solvent to the quinazolinone skeleton have been used. These make use of solid catalyst systems such as (SiO 2 /H 2 SO 4 ) (Montazeri and Rad-Moghadam, 2004 ), montmorillonite K-10 (Dabiri et al, 2004b ), AlCl 3 /ZnCl 2 -SiO 2 (Dabiri et al, 2005 ), and HY-zeolite (Bakavoli et al, 2007 ; Montazeri et al, 2012a ), as well as organocatalysts, including pentafluorophenylammonium triflate (PFPAT) (Montazeri et al, 2012b ).…”

Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products

“…Recently, metal-catalyzed one-pot oxidative cyclization of 2-amino benzamide with aldehyde has been recognized as an attractive method to form quinazolinones. − Very recently, Wang and co-workers reported the synthesis of 2-substituted quinazolin-4­(3 H )-one via a palladium-catalyzed one-pot reaction on 2-nitrobenzamide . Similarly, Das and co-workers established a zinc catalyzed approach for the synthesis of 2-substituted quinazolinones from 2-amino benzamide and benzyl alcohols .…”

“…Similarly, Das and co-workers established a zinc catalyzed approach for the synthesis of 2-substituted quinazolinones from 2-amino benzamide and benzyl alcohols . The groups of Wang, Paul, Watson, and some others independently reported the synthesis of quinazolinones from o -amino benzamides using Ru-, Ni-, Cu-, and Mn as catalysts. In spite of the significant utility, most of the above-mentioned methods need multistep transformation for the synthesis of starting materials .…”