Efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by titanium silicon oxide nanopowder in aqueous media

Mekala, Ramamohan; Madhubabu, M. V.; Dhanunjaya, G.; Ramaswamy, Sridhar; Chandrasekhar, K. B.; Jayaprakash, Sarva

doi:10.1080/00397911.2016.1254801

Cited by 23 publications

(6 citation statements)

References 18 publications

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“…Mekala et al reported that the 2, 3-dihydroquinazolin-4(1H)-one 94 derivative was obtained in 93 % yield using a onepot, three-component condensation reaction of isatoic anhydride 93, 2-chloro benzaldehyde 7, and ammonium acetate 4 in the presence of titanium silicon oxide nanopowder as catalyst in 1,4-dioxane solvent. [42] The catalyst may be regenerated up to four times without adversely impacting yield or catalytic efficiency (Scheme 34, Table 23). Alinezhad et al synthesized 2,3-dihydroquinazolin-4(1H)ones 97 though cyclocondensation of 2-aminobenzamide 95 and 4-cyanobenzaldehyde 96 in aqueous medium using 12tungstophosphoric acid supported on silica gel (PW/SiO 2 ) as a recyclable solid acid catalyst with good to excellent yields (Scheme 35, Table 24).…”

Section: Chemistryselectmentioning

confidence: 99%

Reusable Nano Catalysed Synthesis of Heterocycles: An Overview

Sonawane¹,

Deore²,

Chavan

2022

ChemistrySelect

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The field of reusable nano‐catalysts has grown rapidly over the last decade. Recently, transition metal catalysed organic reactions have attracted considerable interest from the pharmaceutical and organic chemistry fields. Synthetic procedures based on such heterogeneous nanocatalysts are easier, less expensive, non‐toxic, and eco‐friendly, producing only the most desirable products in higher yields and allowing for easy catalyst separation. Heterogeneous nano‐catalysts were highly preferred over homogeneous catalysts for the synthesis of heterocyclic compounds due to their effective separation processes for both products and catalysts. According to recent studies, nanoparticles (NPs) are commonly used as a heterogeneous catalyst in the production of heterocyclic compounds. Heterogeneous catalysts are widely used in a variety of organic reactions due to their high surface‐to‐volume ratio. Most importantly, after the reaction is complete, easy magnetic separation of the catalyst minimises the requirement for catalyst filtration. Additionally, magnetic NPs, particularly supported magnetic nanocatalysts, have garnered considerable interest in both academic and industrial research due to their effectiveness as alternatives to traditional materials, their ease of separation via an external magnet, and their high degree of chemical stability in a variety of organic and inorganic solvents. To reach its depth, this review is focused on the most recent examples, their preparation, synthetic strategies and recycling studies of highly excited catalytic systems used for the synthesis of heterocyclic compounds.

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Section: Chemistryselectmentioning

confidence: 99%

Reusable Nano Catalysed Synthesis of Heterocycles: An Overview

Sonawane¹,

Deore²,

Chavan

2022

ChemistrySelect

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“…A three‐component reaction of primary amines or ammonium acetate in the presence of aldehydes and isatoic anhydride ( 20 ) in aqueous media catalyzed by titanium silicon oxide for the efficient preparation of 2,3‐dihydroquinazolin‐4(1H)‐one derivatives ( 24 ) was accomplished as shown in Scheme . As shown in Scheme , 2‐substituted derivatives of quinazolin‐4(3H)‐ones ( 25 ) were synthesized from the reaction of 20 with amidoximes in presence of iron (III) chloride…”

Section: Synthesismentioning

confidence: 99%

Remarkably flexible quinazolinones—synthesis and biological applications

Reddy

Sivaramakrishna

2019

Journal of Heterocyclic Chem

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Even though several quinazolinone derivatives have been synthesized, still there is a constant demand for designing and synthesis of new quinazolinone derivatives by fine‐tuning the electronic and steric properties of substituents due to their interesting structure‐based biological utilities and the versatile chemistry. While many of the synthetic routes are useful as building blocks in synthetic organic chemistry, the drawbacks of some of these methods like unsatisfactory or variable yields, prolonged reaction times, inadequate tolerance to other substrates, including the use of costly catalysts/reagents. This review article is mainly focused on various synthetic routes for the preparation of quinazolinones, their important properties and applications.

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“…94 The integration of mesoporous silica with magnetic NPs is certainly of great interest for practical applications. As shown in Table 3, different silica-supported NPs were used as catalysts for the one-pot three-component reaction, leading to 45-97% yield in 1-8 h. [95][96][97][98][99] The use of solid acids, as non-toxic, low-cost and reusable catalysts, has also emerged in the synthesis of DHQs (Table 3). Among them, several acids bearing sulfonic moiety supported on silica catalyzed the multi-component synthesis under different conditions, providing DHQs with >70% yield in 0.5-7 h. [100][101][102][103][104] MCM-41 is another type of ordered mesoporous silica material.…”

Section: Heterogeneous and Reusable Catalystsmentioning

confidence: 99%