Poly(4-vinylpyridine) supported acidic ionic liquid: A novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation

Abstract

A novel poly(4-vinylpyridine) supported acidic ionic liquid catalyst was synthesized by the reaction of 4-vinylpyridine with 1,3-propanesultone, followed by the polymerization and the addition of the heteropolyacid. Due to the combination of polymer features and ionic liquid, it acted as a heterogeneous catalyst to effectively catalyze the cyclocondensation reaction of anthranilamide with aldehydes under ultrasonic irradiation and afforded the corresponding 2,3-dihydro-4(1H)-quinazolinones compounds in good to excellent yields. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity. More importantly, the use of ultrasonic irradiation can obviously accelerate the reaction.

Use of Ultrasound in the Synthesis of Heterocycles of Medicinal Interest

“…Synthesis of pyrimidine/pyridine derivatives has been reported by numerous methods [83][84][85][86][87][88][89] previously. The first group of pyrimidine derivatives (92) was prepared in aqueous NaOH solution, by the addition of aromatic aldehyde (90) to acetyl acetone (89) and thiourea (91) (Scheme 23(a)). The first group of pyrimidine derivatives (92) was prepared in aqueous NaOH solution, by the addition of aromatic aldehyde (90) to acetyl acetone (89) and thiourea (91) (Scheme 23(a)).…”

“…Wang et al [91] developed a poly(4-vinylpyridine)-supported acidic ionic liquid (104), and used it as catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones (105) under ultrasonication. The reaction of 4-vinylpyridine and 1,3-propanesultone followed by the polymerization and the addition of the heteropolyacid afforded the ionic liquid that subsequently acted as a heterogeneous catalyst in the cyclocondensation reaction of anthranilamide (102) with aldehydes (103) providing 105 in higher yields on sonication (Scheme 25).…”

Synthesis of P123‐Templated and DVB‐Cross‐linked Meso‐macroporous Poly (ionic liquids) with High‐Performance Alkylation

“…Xia has prepared a highly‐crosslinked nonporous PILs xerogel with very high SO 2 adsorption capacity (498 mg·g −1 ) through the photopolymerization of Gemini ionic liquid monomers. Wang has prepared a novel acidic poly(4‐vinylpyridine) supported ionic liquid for effectively catalyzing the anthranilamide cyclocondensation with aldehydes under ultrasound exposure. Thus, the channel structure and surface area of PILs are controllable via appropriate reaction conditions and reaction system.…”

Functional mesoporous poly (ionic liquid) derived from P123: From synthesis to catalysis and alkylation of styrene and o‐xylene

“…The catalyst was shown to be an efficient dual acidic organocatalyst for Biginelli reaction under mild reaction conditions in high yields. Junke Wang et al prepared a novel poly(4‐vinylpyridine) supported acidic ionic liquid catalyst which acted as a heterogeneous catalyst to effectively catalyze the cyclocondensation reaction of anthranilamide with aldehydes under ultrasonic irradiation . Except for the above studies, some researchers and scholars started to report porous PILs materials.…”