- Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones fromo-nitrobenzamide and alcohols
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Palladium-catalyzed 2-substituted quinazolin-4(3H)-one formation from readily availableo-nitrobenzamides and alcohols using hydrogen transfer is described. Various quinazolin-4(3H)-ones were obtained in good to high yields. The cascade reaction including
- Wang, Ke,Chen, Hao,Dai, Xinyan,Huang, Xupeng,Feng, Zhiqiang
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- Preparation method of quinazolinone derivative
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The invention discloses a preparation method of a quinazolinone derivative, wherein the preparation method comprises the following steps: dissolving an anthranilonitrile compound represented by a formula I and an aldehyde represented by a formula II in a
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Paragraph 0083-0086
(2021/04/14)
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- Copper-mediated synthesis of quinazolin-4(3: H)-ones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides
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An efficient copper-mediated tandem C(sp2)-H amination to provide quinazolinones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides has been developed. It can afford rather complex products in a single step synthesis from easily availab
- Ban, Zihui,Cui, Xinfeng,Hu, Fangpeng,Lu, Guoqiang,Luo, Nan,Huang, Guosheng
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supporting information
p. 12963 - 12966
(2019/08/28)
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- Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability
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Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4(3H)-ones using mesityl(2,2,2-trifluoroethyl)iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C-H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4(3H)-one family associated with nonradiative decay is presented.
- Maiti, Saikat,Kim, Jaeshin,Park, Jae-Heon,Nam, Dongsik,Lee, Jae Bin,Kim, Ye-Jin,Kee, Jung-Min,Seo, Jeong Kon,Myung, Kyungjae,Rohde, Jan-Uwe,Choe, Wonyoung,Kwon, Oh-Hoon,Hong, Sung You
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supporting information
p. 6737 - 6751
(2019/06/04)
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- Polystyrene-Supported Palladium (Pd?PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones
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An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd?PS) nanoparticles (NPs) catalyzed con
- Ram, Shankar,Shaifali,Chauhan, Arvind Singh,Sheetal,Sharma, Ajay Kumar,Das, Pralay
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supporting information
p. 14506 - 14511
(2019/11/21)
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- Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles
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A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.
- Wang, Qi,Lv, Miao,Liu, Jianping,Li, Yang,Xu, Qing,Zhang, Xu,Cao, Hongen
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p. 3043 - 3048
(2019/03/17)
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- Method for synthesizing quinazolinone derivative
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The invention discloses a method for synthesizing a quinazolinone derivative. According to the method for synthesizing the quinazolinone derivative,anthranilonitrile compounds and primary alcohols areused as raw materials, 2,2,6,6-tetramethylpiperidine ox
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Paragraph 0082-0085
(2019/11/04)
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- A quinazolinone of heterocyclic compound synthetic method
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The invention discloses a quinazolinone of heterocyclic compound synthetic method. In under the action of the water-soluble alkali using air as the oxidizing agent, and ortho-amino alcohol oxidation fragrant nitrile compound - cyclized - oxidation of high efficiency series reaction one-step preparation quinazolinone of heterocyclic compound synthetic method. This method does not need the use of expensive transition metal catalyst and ligand, but the use of water-soluble alkali as promoter, the alkali can be removed by water washing mode is convenient, so product transition metal-free residue, is suitable as a pharmaceutical preparation of the precursor, the method condition is simple, easy to operate, low requirement for the device, and can utilizes air as economic security green oxidizing agent, water-soluble alkali as promoter, the only by-product is water, atom economical high, has a certain research and industrial application prospect.
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Paragraph 0127-0130
(2019/07/01)
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- Direct diversification of unmasked quinazolin-4(3: H)-ones through orthogonal reactivity modulation
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Here we report a set of direct functionalization methods of unmasked 2-phenylquinazolin-4(3H)-ones, a privileged alkaloid core, without the installation/removal event of protecting groups or exogenous coordinating moieties. Divergent pathways were modulated with transition-metal catalysts by suppressing competitive reactivities, leading to N-arylation, annulative π-extension, or C-H fluorination.
- Lee, Jae Bin,Kang, Mi Eun,Kim, Joohee,Lee, Chang Young,Kee, Jung-Min,Myung, Kyungjae,Park, Jang-Ung,Hong, Sung You
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supporting information
p. 10394 - 10397
(2017/09/25)
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- Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
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A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
- Wang, Zhen-Zhen,Tang, Yu
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p. 1330 - 1336
(2017/02/15)
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- Iron(III) Chloride-Catalyzed Decarboxylative-Deaminative Functionalization of Phenylglycine: A Tandem Synthesis of Quinazolinones and Benzimidazoles
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The first iron(III) chloride-catalyzed decarboxylative-deaminative functionalization of phenylglycine with o-substituted nitroarenes was achieved for the synthesis of 4(3H)-quinazolinones and benzimidazoles. The reaction of 2-nitrobenzonitrile/2-nitro-N,N-diphenylamine with phenylglycine at 120 C in the presence of potassium carbonate as a base in toluene generated the products in 45-87% yields. Various functional groups like nitro, fluoride, chloride and trifluoromethyl were well tolerated under the present reaction conditions. In this tandem approach, involvement of transfer hydrogenation of the nitro functionality with in situ generated ammonia, imination, nitrile hydration to amide and oxidative cyclization sequences have been established. The process avoids the use of an external hydrogen source, costly catalysts as well as the isolation of amine and amide intermediates.
- Kumar, Manoranjan,Richa,Sharma, Sushila,Bhatt, Vinod,Kumar, Neeraj
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supporting information
p. 2862 - 2868
(2015/09/28)
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