Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3H bond activation using a new metal-organic framework as catalyst

To, Tuong A.; Vo, Yen H.; Nguyen, Hoa Thi; Ha, Phuong T.M.; Doan, Son H.; Đoàn, Tân Lê Hoàng; Li, Shuang; Le, Ha V.; Tu, Thach N.; Phan, Nam T. S.

doi:10.1016/j.jcat.2018.11.031

Cited by 47 publications

(8 citation statements)

References 45 publications

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“…VNU-20 was utilized as a recyclable catalyst for the functionalization of coumarins with N,N-dimethylanilines (yield 84%) via direct C− H bond activation. To et al 107 synthesized VNU-21 [Fe 3 (BTC)(EDB) 2 •12.27H 2 O] via a mixed-linker synthetic strategy using 1,3,5-benzenetricarboxylic acid, 4,4′-ethynylenedibenzoic acid, and FeCl 2 . VNU-21 was consequently used as a recyclable heterogeneous catalyst in the one-pot synthesis of quinazolinones via two steps under an oxygen atmosphere.…”

Section: Catalysis On Decorated Mofs (De Novo Synthesis or Post Treat...mentioning

confidence: 99%

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

et al. 2020

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More than 95% (in volume) of all today's chemical products are manufactured through catalytic processes, making research into more efficient catalytic materials a thrilling and very dynamic research field. In this regard, Metal Organic Frameworks (MOFs) offer great opportunities for the rational design of new catalytic solids, as highlighted by the unprecedented number of publications appearing over the last decade. In this review, the recent advances in the application of MOFs in heterogeneous catalysis are discussed. MOFs with intrinsic thermo-catalytic activity, as hosts for the incorporation of metal nanoparticles, as precursors for the manufacture of composite catalysts and those active in photo and electrocatalytic processes are critically reviewed. The review is wrapped up with our personal view on future research directions.

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Section: Catalysis On Decorated Mofs (De Novo Synthesis or Post Treat...mentioning

confidence: 99%

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

et al. 2020

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“…In another study, biological active nitrogen-containing quinazolinones were synthesized in the presence of mixed-linker iron-based MOF [Fe 3 (BTC) (EDB) 2 12.27H 2 O] (7) as a catalyst, where BTC 1,3,5benzenetricarboxylate and EDB 2-4,4′-ethynylenedibenzoate. Phenylacetic acid and 2-aminobenzamide underwent a one-pot chemical reaction to form 2-phenylquinazolin-4(3H)-one in the presence of iron-based MOF produced excellent yields compared to other solid catalysts like Fe 3 O(BDC) 3 , Fe 3 O(BPDC) 3 , Cu 2 (OBA) 2 (BPY), Cu-MOF-199 and Co-ZIF-67 (Nakanishi and Bolm, 2007;To et al, 2019). The iron-catalyzed decarboxylation of phenylacetic acid through SP 3 hybridised carbon and hydrogen bond activation, accelarates the cyclization of intermediate with 2aminobenzamides to produce the target product, quinazolinone.…”

Section: Cu (Ii) Basedmentioning

confidence: 99%

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

Gangu

Jonnalagadda

2021

Front. Chem.

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Metal-organic frameworks (MOFs) have emerged as versatile candidates of interest in heterogeneous catalysis. Recent research and developments with MOFs positively endorse their role as catalysts in generating invaluable organic compounds. To harness the full potential of MOFs in value-added organic transformation, a comprehensive look at how these materials are likely to involve in the catalytic processes is essential. Mainstays of MOFs such as metal nodes, linkers, encapsulation materials, and enveloped structures tend to produce capable catalytic active sites that offer solutions to reduce human efforts in developing new organic reactions. The main advantages of choosing MOFs as reusable catalysts are the flexible and robust skeleton, regular porosity, high pore volume, and accessible synthesis accompanied with cost-effectiveness. As hosts for active metals, sole MOFs, modified MOFs, and MOFs have made remarkable advances as solid catalysts. The extensive exploration of the MOFs possibly led to their fast adoption in fabricating new biological molecules such as pyridines, quinolines, quinazolinones, imines, and their derivatives. This review covers the varied MOFs and their catalytic properties in facilitating the selective formation of the product organic moieties and interprets MOF’s property responsible for their elegant performance.

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“…Due to the pharmacological importance of the quinazolinone moiety, in recent years the development of new synthetic methods to access this class of compounds has attracted attention in organic synthesis. Generally, the quinazolinones are synthesized by the condensation of o-aminobenzamides with aldehydes [10], phenylacetic acid [11] and alcohols [12,13]. Other important protocols include carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes [14], oxidative annulation of alcohols with o-aminoarylnitriles [15], and Cu-catalyzed oxidative annulation of anilines, alkylamines and aldehydes [16].…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction

et al. 2021

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We describe here our results from the copper-catalyzed three component reaction of 2-azidobenzaldehyde, anthranilamide and terminal alkynes, using Et3N as base, and DMSO as solvent. Depending on the temperature and amount of Et3N used in the reactions, 1,2,3-triazolyl-quinazolinones or 1,2,3-triazolyl-dihydroquinazolinone could be obtained. When the reactions were performed at 100 °C using 2 equiv. of Et3N, 1,2,3-triazolyl-dihydroquinazolinone was formed in 82% yield, whereas reactions carried out at 120 °C using 1 equiv. of Et3N provided 1,2,3-triazolyl-quinazolinones in moderate-to-good yields.

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Iron-catalyzed one-pot sequential transformations: Synthesis of quinazolinones via oxidative Csp3H bond activation using a new metal-organic framework as catalyst

Cited by 47 publications

References 45 publications

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

A Review on Metal-Organic Frameworks as Congenial Heterogeneous Catalysts for Potential Organic Transformations

Selective Synthesis of 2-(1,2,3-Triazoyl) Quinazolinones through Copper-Catalyzed Multicomponent Reaction

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