[bmim]HSO₄: an efficient and reusable catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones

Abstract

Various di-and mono-substituted quinazolinones were synthesized by one-pot condensation of isatoic anhydride, aldehyde and amine, or ammonium carbonate using [bmim]HSO 4 as catalyst in aqueous medium. Water as a reaction media, recyclability of catalyst, shorter reaction time, and good yields (70Á90%) are some of the salient features of the developed protocol.

Synthesis and characterization of glucosulfonic acid supported on Fe3O4 nanoparticles as a novel and magnetically recoverable nanocatalyst and its application in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives

“…Also, 2,3-Dihydro-4(1H)quinazolinones are important bicyclic heterocycles which have emerged as versatile biologically active compounds possessing applications as diuretic, vasodilating, tranquilizing, antitumor, antidefibrillatory, antibiotic, antihistaminic, anticonvulsant, anticancer, herbicidal activity, plant growth regulation ability and antihypertensive agents [4,10,28]. They are also reported to possess the ability to inhibit enzymes of biological importance [29]. In addition, these compounds can be easily oxidized to their quinazolin-4(3H)-one analogues [10], which also include important pharmacologically active compounds, Generally, 2,3dihydroquinazolin-4(1H)-ones were prepared using the reductive cyclization of aldehydes or ketones with 2aminobenzamide in the presence of acid catalysts [9,29].…”

“…In addition, these compounds can be easily oxidized to their quinazolin-4(3H)-one analogues [10], which also include important pharmacologically active compounds, Generally, 2,3dihydroquinazolin-4(1H)-ones were prepared using the reductive cyclization of aldehydes or ketones with 2aminobenzamide in the presence of acid catalysts [9,29]. For these reasons, many methods have been developed including microwave and ultrasound irradiation techniques using various catalytic systems [26][27][28][29]. Although, most of these processes suffer from one or several drawbacks such as longer reaction time, tedious workup, harsh reaction conditions, unsatisfactory yields, use of large quantity of environmentally toxic and expensive catalysts.…”

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.…”

Synthesis of 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones under solvent free conditions using ionic liquid as a mild and efficient catalyst

“…Protic and Bronsted basic liquids, in particular, have received increasing attention for carrying out organic transformations as they can replace volatile organic solvents as well as highly acidic catalytic systems [24][25]. Hence uses of ionic liquids have been found advantageous as they usually involve in simple reaction processes as compared to most of the traditional methods [23].…”

“…Due to their chemical properties, such as recyclability, negligible vapor pressure, ability to dissolve wide range of substrates and catalysts, thermal stability. Ionic liquids have been considered as viable alternatives to the conventional volatile organic solvents [19][20][21][22][23]. Protic and Bronsted basic liquids, in particular, have received increasing attention for carrying out organic transformations as they can replace volatile organic solvents as well as highly acidic catalytic systems [24][25].…”