- A convenient access to 2,4-disubstituted quinazolines via one-pot three-component reaction under mild conditions?
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A new and practical method has been developed for the synthesis of 2,4-disubstituted quinolines via one-pot three-component reaction of o-amino arylketones, aldehydes and ammonium acetate in high yields by using DDQ in CH3CN under mild conditio
- Bose, D. Subhas,Ramesh, Nukala
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- A new triazine-cored covalent organic polymer for catalytic applications
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A triazine based covalent organic polymer (CC-TAPT-COP) was designed and synthesized via nucleophilic substitution reaction between 1,3,5-tris-(p-aminophenyl) triazine and cyanuric chloride under refluxing conditions with bottom-up approach. The structura
- Subodh,Prakash, Kunal,Chaudhary, Karan,Masram, Dhanraj T.
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- TMSOTf-catalyzed synthesis of substituted quinazolines using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
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In this article, we report an efficient and mild synthetic route for the construction of substituted quinazolines from functionalized 2-aminobenzophenones with various benzaldehydes usingcat. TMSOTf and hexamethyldisilazane (HMDS) under neat, metal-free and microwave irradiation conditions in which gaseous ammonia was formedin situ. This synthetic protocol provided the desired quinazolines with a broad substrate scope in good to excellent yields. Some structures were confirmed by X-ray single-crystal diffraction analysis.
- Chan, Chieh-Kai,Lai, Chien-Yu,Wang, Cheng-Chung
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p. 7201 - 7212
(2020/10/02)
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- Molecular Iodine Catalysed Benzylic sp 3 C-H Bond Amination for the Synthesis of 2-Arylquinazolines from 2-Aminobenzaldehydes, 2-Aminobenzophenones and 2-Aminobenzyl Alcohols
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Molecular iodine catalysed benzylic sp 3 C-H bond amination has been developed for the synthesis of quinazolines from 2-aminobenzaldehydes and 2-aminobenzophenones with benzylamines. The use of oxygen as a green oxidant combined with the transition-metal-, additive- and solvent-free conditions makes the methodology economical and greener. The lack of aqueous work up also enhances the efficiency of this protocol. A series of 2-arylquinazolines was synthesised in good to excellent yields by using the developed protocol. 2-Aminobenzyl alcohols could also be employed to prepare the corresponding quinazoline derivatives.
- Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
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supporting information
p. 979 - 985
(2018/04/23)
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- Four-component quinazoline synthesis from simple anilines, aromatic aldehydes and ammonium iodide under metal-free conditions
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A four-component procedure for the preparation of substituted quinazolines from anilines, aromatic aldehydes and ammonium iodide is described. The C-H bond ortho to the amino group in anilines was directly functionalized under metal-free conditions. Two a
- Chen, Jinjin,Chang, Dan,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 5459 - 5463
(2019/01/03)
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- Copper-Catalyzed Synthesis of Substituted Quinazolines from Benzonitriles and 2-Ethynylanilines via Carbon-Carbon Bond Cleavage Using Molecular Oxygen
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A copper-catalyzed process for the synthesis of substituted quinazolines from benzonitriles and 2-ethynylanilines using molecular oxygen (O2) as sole oxidant is described. The mild catalytic system enabled the effective cleavage of the C-C triple bond and construction of new C-N and C-C bonds in one operation. Furthermore, the compound N,N-dimethyl-4-(2-(4-(trifluoromethyl)phenyl)quinazolin-4-yl)aniline (3dj) exhibited obvious aggregation-induced emission phenomenon, and the fluorescence quantum yield (ΦF,film) and lifetime (τfilm) were measured to be 45.5% and 5.8 ns in thin films state, respectively.
- Wang, Xu,He, Dandan,Huang, Yubing,Fan, Qihang,Wu, Wanqing,Jiang, Huanfeng
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p. 5458 - 5466
(2018/05/28)
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- Palladium-Catalyzed Three-Component Tandem Process: One-Pot Assembly of Quinazolines
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The first example of the palladium-catalyzed, three-component tandem reaction of 2-aminobenzonitriles, aldehydes, and arylboronic acids has been developed, providing a new approach for one-pot assembly of diverse quinazolines in moderate to good yields. A noteworthy feature of this method is the tolerance of bromo and iodo groups, which affords versatility for further synthetic manipulations. Preliminary mechanistic experiments indicate that this tandem process involves two possible mechanistic pathways for the formation of quinazolines via catalytic carbopalladation of the cyano group.
- Hu, Kun,Zhen, Qianqian,Gong, Julin,Cheng, Tianxing,Qi, Linjun,Shao, Yinlin,Chen, Jiuxi
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supporting information
p. 3083 - 3087
(2018/05/28)
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- Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage
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An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.
- Prakash, Rashmi,Bora, Bidisha R.,Boruah, Romesh C.,Gogoi, Sanjib
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p. 2297 - 2300
(2018/04/30)
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- Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
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A single-pot procedure for the synthesis of 2,4-diarylquinazolines is described which involves a silver oxide-mediated C–H activation/C–N bond formation process. The generality of this method with respect to substituent effects is presented along with studies leading to process optimization. Mechanistic investigations provide support for the involvement of radical intermediates in the reaction process.
- Cheung, Wing,Patch, Raymond J.,Player, Mark R.
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p. 2368 - 2371
(2018/05/25)
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- Synthesis of quinazolines over recyclable Fe3O4@SiO2-PrNH2-Fe3+ nanoparticles: A green, efficient, and solvent-free protocol
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A practical and efficient method is developed for efficient synthesis of quinazoline derivatives through condensation reaction of 2-aminoaryl ketone, an aldehyde, and ammonium acetate, over magnetic Fe3O4@SiO2-PrNH2/
- Eidi, Esmaiel,Kassaee, Mohamad Z.,Nasresfahani, Zahra,Cummings, Peter T.
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- Efficient synthesis of quinazoline derivatives catalyzed by flourinated alcohol
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A facile and efficient protocol is reported for the synthesis of quinazoline derivatives via a one-pot multicomponent reaction of 2-amino-5-chlorobenzophenone, aromatic aldehydes and ammonium acetate using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). The use
- Maleki, Behrooz,Mofrad, Akram Vedad
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p. 3111 - 3120
(2017/04/19)
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- Copper-catalyzed aerobic oxidative decarboxylative amination of arylacetic acids: A facile access to 2-arylquinazolines
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An efficient copper-catalyzed oxidative decarboxylative amination of arylacetic acids with 2-aminobenzoketones and ammonium acetate under an oxygen atmosphere was first developed. This reaction represents a novel avenue for 2-arylquinazolines in good to e
- Yan, Yizhe,Shi, Miaomiao,Niu, Bin,Meng, Xiangping,Zhu, Changrui,Liu, Gengyao,Chen, Ting,Liu, Yanqi
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p. 36192 - 36197
(2016/05/19)
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- 2-subsituted quinazoline preparation method
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The present invention discloses a 2-subsituted quinazoline preparation method, in particular, 2-subsituted quinazoline is obtained by oxidative decarboxylation and condensation oxidation reaction of o-amino phenyl ketone, an aryl acetic acid and an inorga
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Page/Page column 15; 16
(2016/10/07)
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- Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines
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A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp3)-C(sp2) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).
- Shen, Zi-Chao,Yang, Pan,Tang, Yu
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p. 309 - 317
(2016/01/15)
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- Synthesis of Quinazolines from N,N′-Disubstituted Amidines via I2/KI-Mediated Oxidative C-C Bond Formation
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An I2/KI-promoted oxidative C-C bond formation reaction from C(sp3)-H and C(sp2)-H bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The required substrates are readily prepared from the corresponding acyl chlorides, anilines, and alkyl/benzylamines by sequential amidation, chlorination, and amination reactions. Under the optimal oxidative cyclization conditions, all these amidines were conveniently transformed into the expected products in moderate to good yields. This practical and environmentally benign approach works well with crude amidine intermediates and can also be carried out on a gram scale.
- Lv, Zhigang,Wang, Bingnan,Hu, Zhiyuan,Zhou, Yiming,Yu, Wenquan,Chang, Junbiao
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p. 9924 - 9930
(2016/11/02)
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- Expanding applications of zeolite imidazolate frameworks in catalysis: Synthesis of quinazolines using ZIF-67 as an efficient heterogeneous catalyst
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A cobalt zeolite imidazolate framework (ZIF-67) was successfully synthesized and characterized by several techniques. The ZIF-67 was used as an efficient heterogeneous catalyst for the cyclization reaction of 2-aminobenzoketones and benzylamine derivatives to form quinazoline products. The optimal conditions involved the use of TBHP oxidant in toluene solvent at 80°C. Remarkably, the ZIF-67 catalyst exhibited better performance in the cyclization reaction than common cobalt salts such as Co(NO3)2, CoCl2, and Co(OAc)2 and other Co-MOFs such as ZIF-9, Co-MOF-74, and Co2(BDC)2(DABCO). In addition, the cyclization reaction could only proceed in the presence of the solid Co-ZIF catalyst and there was no contribution from leached active sites present in the solution. The catalyst could be recovered and reused several times without a significant degradation in catalytic activity.
- Truong, Thanh,Hoang, Tam M.,Nguyen, Chung K.,Huynh, Quynh T. N.,Phan, Nam T. S.
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p. 24769 - 24776
(2015/03/18)
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- An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
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An efficient green protocol for the synthesis of quinazolines in the absence of solvent and catalyst has been developed. 2,4-Disubstituted quinazolines have been synthesized from three-component one-pot reactions of 2-aminoaryl ketones, orthoesters, and ammonium acetate. The present method has advantages of operational simplicity, substrate generality, clean reaction, high yields (76-94%), and moderate reaction time. The plausible mechanism of the reaction has been proposed based on the spectral characterization and single crystal X-ray analysis of isolated intermediate.
- Bhat, Subrahmanya Ishwar,Das,Trivedi, Darshak R.
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p. 1253 - 1259
(2015/08/06)
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- Potassium iodide-catalyzed three-component synthesis of 2-arylquinazolines via amination of benzylic C-H bonds of methylarenes
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A novel potassium iodide-catalyzed three-component synthesis of quinazolines via benzylic C-H bonds amination was developed. Commonly used ammonia salt and the sp3 carbon in commercially available methylarenes were used as nitrogen and C1 sources, respectively. Mechanistic studies indicated that an aryl aldehyde is involved as a key intermediate in the reaction.
- Zhao, Dan,Shen, Qi,Li, Jian-Xin
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supporting information
p. 339 - 344
(2015/03/04)
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- Efficient synthesis of 2-arylquinazolines via copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes
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A novel copper-catalyzed dual oxidative benzylic C-H aminations of methylarenes with 2-aminobenzoketones in the presence of ammonium acetate was developed. This reaction represents a new avenue for 2-arylquinazolines with good yields. A key intermediate was detected and the kinetics isotope effect (KIE) indicated that C-H bond cleavage was the rate-determining step.
- Liu, Li-Yan,Yan, Yi-Zhe,Bao, Ya-Jie,Wang, Zhi-Yong
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p. 1216 - 1220
(2015/12/30)
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- A new and facile CuCl2·2H2O-catalyzed one-pot three-component synthesis for quinazolines
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A new and facile CuCl2·2H2O-catalyzed one-pot three-component synthesis for quinazolines has been developed. A mixture of readily available 2-amino-5-chlorobenzophenones, substituted benzaldehydes, ammonium acetate, and CuCl2/s
- Saad, Syed Muhammad,Khan, Khalid Mohammed,Perveen, Shahnaz,Voelter, Wolfgang,Taha, Muhammad
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p. 1877 - 1880
(2015/10/29)
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- Synthesis of quinazolines via CuO nanoparticles catalyzed aerobic oxidative coupling of aromatic alcohols and amidines
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CuO nanoparticles were found to be efficient catalysts for the synthesis of quinazoline derivatives; twenty-four products were obtained with good to excellent yields via reaction of N-arylamidines and aromatic aldehydes or benzyl alcohol in air. Neither a
- Zhang, Wu,Guo, Fei,Wang, Fei,Zhao, Na,Liu, Liang,Li, Jia,Wang, Zhenghua
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p. 5752 - 5756
(2014/07/22)
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- Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines
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A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp3)-C(sp2) and C(sp 2)-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp3C-H/sp2C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.
- Lin, Jian-Ping,Zhang, Feng-Hua,Long, Ya-Qiu
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p. 2822 - 2825
(2014/06/23)
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- One-pot synthesis of quinazoline derivatives via [2+2+2] cascade annulation of diaryliodonium salts and two nitriles
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An efficient one-pot approach to multiple substituted quinazolines with diaryliodonium salt 1, and two nitriles 2 has been presented. The reaction enables great flexibility of the substitution patterns on quinazolines and is applicable to two different nitriles to give a regio-selective product.
- Su, Xiang,Chen, Chao,Wang, Yong,Chen, Junjie,Lou, Zhenbang,Li, Ming
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supporting information
p. 6752 - 6754
(2013/07/26)
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- Recyclable, magnetic ionic liquid bmim[FeCl4]-catalyzed, multicomponent, solvent-free, green synthesis of quinazolines
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An atom-efficient, eco-friendly, solvent-free, high yielding, multicomponent green strategy to synthesize highly functionalized quinazoline derivatives by the one-pot reaction of 2-aminobenzophenone, aromatic aldehyde and ammonium acetate is presented. Ma
- Panja, Sumit Kumar,Saha, Satyen
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p. 14495 - 14500
(2013/09/02)
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- Recyclable graphite oxide promoted efficient synthesis of 2-phenyl quinazoline derivatives in the presence of TBHP as an oxidant
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A novel and efficient protocol for the synthesis of 2-phenyl quinazoline derivatives is developed by recyclable graphite oxide as a catalyst, devoid of moisture sensitive metal catalysts and corrosive acidic reagents. This new procedure has afforded the desired products in good to excellent yields. The graphite oxide can be synthesized by a simple adoptable procedure from inexpensive and readily available graphite and is recoverable and reusable up to four cycles, without any loss of activity.
- Karnakar,Kumar, A. Vijay,Murthy, S. Narayana,Ramesh,Nageswar
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supporting information; experimental part
p. 4613 - 4617
(2012/09/22)
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- DDQ/TBHP-induced oxidative cyclization process: A metal-free approach for the synthesis of 2-phenylquinazolines
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Various 2-phenylquinazoline derivatives were synthesized under metal-free conditions from readily available 2-aminophenyl ketones and benzylamines via condensation and oxidative cyclization using 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (DDQ) as a versatile reagent. The reaction gave the corresponding 2-phenylquinazoline derivatives in good to excellent yields (up to 92%). Georg Thieme Verlag Stuttgart ? New York.
- Rachakonda, Sridhar,Pratap, P.Surya,Basaveswara Rao, Mandava V.
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experimental part
p. 2065 - 2069
(2012/08/07)
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- Catalyst-free synthesis of quinazoline derivatives using low melting sugar-urea-salt mixture as a solvent
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Low melting mixture of maltose-dimethylurea (DMU)-NH4Cl was found to be an inexpensive, non-toxic, easily biodegradable and effective reaction medium in the catalyst-free synthesis of quinazoline derivatives. This simple and efficient method fu
- Zhang, Zhan-Hui,Zhang, Xiao-Nan,Mo, Li-Ping,Li, Yong-Xiao,Ma, Fei-Ping
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experimental part
p. 1502 - 1506
(2012/06/04)
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- An efficient protocol for the synthesis of 2-phenylquinazolines catalyzed by ceric ammonium nitrate (CAN)
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A facile and efficient method for the synthesis of 2-phenylquinazolines has been developed from 2-aminobenzophenones and benzylamines catalyzed by ceric ammonium nitrate (CAN)-TBHP in acetonitrile. The corresponding 2-phenylquinazolines were obtained in good to excellent yields. Georg Thieme Verlag Stuttgart - New York.
- Karnakar,Shankar,Murthy, S. Narayana,Ramesh,Nageswar
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supporting information; experimental part
p. 1089 - 1096
(2011/06/20)
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- Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
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A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
- Yan, Yizhe,Wang, Zhiyong
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p. 9513 - 9515
(2011/10/01)
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- A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
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A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
- Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
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supporting information; experimental part
p. 5244 - 5246
(2010/09/05)
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- A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
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(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
- Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
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supporting information; experimental part
p. 2841 - 2843
(2010/09/04)
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- Ecofriendly and efficient one-pot procedure for the synthesis of quinazoline derivatives catalyzed by an acidic ionic liquid under aerobic oxidation conditions
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A three-component condensation reaction between 2-aminobenzophenone derivatives, formaldehyde or aromatic aldehydes, and ammonium acetate efficiently provides substituted quinazolines in a one-pot reaction in the presence of Bronsted acidic ionic liquid, 1-methylimidazolium triflouroacetate ([Hmim]TFA), in conjunction with aerobic oxidation. The ionic liquid was separated from the reaction mixture by simple extraction and was recycled three times without considerable loss in activity. Copyright Taylor & Francis Group, LLC.
- Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh
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experimental part
p. 3214 - 3225
(2010/12/24)
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- SYNTHESIS OF QUINAZOLINES
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Grignard reagents reacted with 2-aminobenzonitrile to give the intermediate (10), which readily could be cyclized to quinazolines by reaction with carbonyl compounds (e.g. acid chlorides, anhydrides, formates and oxalates).The intermediate (10) and aldehy
- Bergman, Jan,Brynolf, Anna,Elman, Bjoern,Vuorinen, Eino
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p. 3697 - 3706
(2007/10/02)
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