Synthesis of 2,3‐Disubstituted Quinazolinone Derivatives through Copper Catalyzed C–H Amidation Reactions

Kotipalli, Trimurtulu; Kavala, Veerababurao; Janreddy, Donala; Bandi, Vijayalakshmi; Kuo, Chun Wei; Yao, Ching Fa

doi:10.1002/ejoc.201501552

Cited by 48 publications

(18 citation statements)

References 67 publications

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“…The results collected in Table 1 showed that the reaction performed under 100 °C using Cs 2 CO 3 as a base provided the highest yield (Entries 1–8, Table 1 ). The further screening of the catalyst (Entries 9–15, Table 1 ) showed that copper (Cu (II)) salts gave higher yields of product 4aa (Entries 12 and 14, Table 1 ) than Cu (I) in this case, being totally different from the reported results [ 11 , 12 , 25 , 29 , 31 ].…”

Section: Discussion and Resultscontrasting

confidence: 86%

“…A variety of convenient methodologies have been developed for the synthesis of quinazolinones [ 10 , 11 , 12 , 13 ]. o -Aminobenzamides [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ] and o -bromobenzamides [ 12 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ] are the most frequently used starting materials by far, and o -Aminobenzoic acid [ 32 ], o -haloaniline [ 26 , 33 ], and isatoic anhydride [ 34 ] were also introduced. Alternatively, o -aminobenzonitrile [ 35 , 36 , 37 ] was applied to prepare quinazolinones by Wu and co-workers [ 35 ], considering that the variation of o -aminobenzonitriles is much more available than o -aminobenzamides.…”

Section: Introductionmentioning

confidence: 99%

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“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

Zibin

Zeng

et al. 2018

Molecules

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A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.

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Section: Discussion and Resultscontrasting

confidence: 86%

Section: Introductionmentioning

confidence: 99%

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

Zibin

Zeng

et al. 2018

Molecules

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“…However, these methods generally suffer from drawbacks such as complex homogeneous catalytic systems or expensive feedstocks. Recent examples of oxidative condensation reactions of alcohols, methyl arenes, and amines often require excess amounts of oxidants (Scheme a, route 2). Wu et al.…”

Section: Methodsmentioning

confidence: 99%

The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru‐clusters/Ceria Catalyst

Wang

Zhang

et al. 2018

Angewandte Chemie

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Quinazolinones, an important class of heterocyclic compounds, have been widely used in pharmaceuticals because of their biological activity. However, the efficient and economical synthesis of quinazolinones has remained a challenge. A novel synthetic approach has now been developed to produce quinazolinones from olefins, CO, and amines over heterogeneous Ru‐clusters/ceria catalyst in the absence of acids, bases, and oxidants. Furthermore, H2O is generated as the only by‐product. A series of quinazolinones with aromatic or non‐aromatic substituents can be obtained in yields of up to 99 %. The Ru‐clusters/ceria can be reused at least four times. The analysis of the E‐factor (environmental impact factor) for the synthesis of 2‐ethyl quinazolinone suggests that this system is more environmentally friendly than other processes reported previously.

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“…In addition, homogeneous copper catalysts have been used successfully for a variety of organic reactions. 36−45 Furthermore, the catalyst systems need to be developed further because of the possibility of metal contamination in the final product, lack of recyclability of the metal catalyst, use of additives, and expensive ligand system. Copper oxide (CuO) nanoparticles (NPs) can be applied in catalysis, gas sensing, and photocatalysis.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous Route for the One-Pot Synthesis of N-Arylamides from Aldoximes and Aryl Halides Using the CuO/Carbon Material

2017

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Metal oxide nanoparticles (NPs) stabilized by porous carbon materials (PCMs) are very promising for catalysis. In this work, monodispersed small and stable copper oxide (CuO) NPs were prepared with an average size of 10–20 nm without using any capping agent and then these NPs were encapsulated into porous carbon. The chemical and structural properties of the CuO/PCM material were characterized by powder X-ray diffraction, electron microscopy, Raman spectroscopy, scanning electron microscopy, transmission electron microscopy, and nitrogen sorption. The obtained CuO/PCM nanocatalytic system has been used for the synthesis of N-arylamides from the reaction of aldoximes and aryl halides. Generally, copper(II) salt was used for the preparation of amides from aldoximes using some ligands and bases, but harsh reaction condition, stoichiometric amount of metal, and lack of recyclability limit their applications in industry. An alternative method is the use of heterogeneous catalysts. More importantly, these heterogeneous catalysts could be easily recycled and reused, showing potential application in organic synthesis.

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Synthesis of 2,3‐Disubstituted Quinazolinone Derivatives through Copper Catalyzed C–H Amidation Reactions

Cited by 48 publications

References 67 publications

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

“On-Water” Synthesis of Quinazolinones and Dihydroquinazolinones Starting from o-Bromobenzonitrile

The Synthesis of Quinazolinones from Olefins, CO, and Amines over a Heterogeneous Ru‐clusters/Ceria Catalyst

Heterogeneous Route for the One-Pot Synthesis of N-Arylamides from Aldoximes and Aryl Halides Using the CuO/Carbon Material

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