- Heterogeneous selective synthesis of 1,2-dihydro-1,3,5-triazines from alcohols and amidines via Cu/OMS-2-catalyzed multistep oxidation
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Copper supported on octahedral manganese oxide molecular sieve (OMS-2) which was obtained via reducing KMnO4 by TBHP was prepared and found to be an efficient catalyst for the synthesis of 1,2-dihydro-1,3,5-triazines directly from alcohols and amidines in one-pot via multistep oxidation. The recyclable heterogeneous catalyst was characterized by BET, XRD, FTIR, TEM and SEM, and the catalytic system can tolerate a wide range of substrates under air with low catalyst loading of supported copper (0.25?mol%), employing OMS-2 as the electron-transfer mediator (ETM) and support.
- Meng, Xu,Bi, Xiuru,Wang, Yanmin,Chen, Gexin,Chen, Baohua,Jing, Zhenqiang,Zhao, Peiqing
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Read Online
- Tropylium-promoted Ritter reactions
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The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.
- Doan, Son H.,Hussein, Mohanad A.,Nguyen, Thanh Vinh
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supporting information
p. 8901 - 8904
(2021/09/10)
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- Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines
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The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).
- Wang, Chao,Rui, Xiyan,Si, Dongjuan,Dai, Rupeng,Zhu, Yueyue,Wen, Hongmei,Li, Wei,Liu, Jian
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supporting information
p. 2825 - 2833
(2021/04/26)
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- STK19 INHIBITORS FOR TREATMENT OF CANCER
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Provided herein are compositions and methods for the treatment and prevention of cancer, including melanoma.
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Paragraph 00417-00418; 00420; 00424-00426
(2020/07/14)
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- Sulfur-Mediated Decarboxylative Coupling of 2-Nitrobenzyl Alcohols and Arylacetic Acids
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We report a new method for the synthesis of substituted quinazolines by the condensation of 2-nitrobenzyl alcohols with arylacetic acids. The transformation requires the use of urea as a nitrogen source, elemental sulfur as a promoter, DABCO as a base, and DMSO as a solvent. Functionalities such as chloro, fluoro, trifluoromethyl, thienyl, and indolyl groups were all compatible with the reaction conditions. Because our method uses stable simple substrates to obtain the N,N-heterocycles in the absence of transition metals, it offers a potential pathway for preparing complex structures under mild conditions.
- Le, Ha V.,Nguyen, Duyen K.,Nguyen, Khang X.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Nam T. S.
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supporting information
p. 1112 - 1116
(2020/07/04)
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- Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
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Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
- Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
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p. 5691 - 5701
(2020/04/10)
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- Visible-Light-Induced Benzylic C-H Functionalization for the Synthesis of 2-Arylquinazolines
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This work reports a mild and efficient approach for the synthesis of substituted quinazolines using 1-(2-aminoaryl)ethan-1-ones in conjunction with arylmethanamines as starting materials via visible-light-induced benzylic C–H functionalization. The reaction proceeded at room temperature with low catalyst loading and the reaction system was clean from beginning to end. Significantly, this method exhibited good tolerance even to free hydroxyl group and amino group contained in substrates.
- Zhang, Jingchang,Wang, Qibao,Guo, Yongen,Ding, Lin,Yan, Maocai,Gu, Yinglin,Shi, Jiajia
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supporting information
p. 5934 - 5936
(2019/10/14)
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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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- Lewis-Acid-Catalysed Activation of Nitriles: A Microwave-Assisted Solvent-Free Synthesis of 2,4-Disubstituted Quinazolines and 1,3-Diazaspiro[5.5]undec-1-enes
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Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3-diazaspiro[5.5]undec-1-ene derivatives through the Lewis-acid-catalysed activation of both aliphatic and aromatic nitriles in a single-step, solvent-free, and transition-metal-free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one-pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.
- Saikia, Ujwal Pratim,Borah, Geetika,Pahari, Pallab
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supporting information
p. 1211 - 1217
(2018/03/21)
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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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- Synthesizing method of drug intermediate quinazoline compound
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The invention relates to a quinazoline compound as shown in formula (5) and capable of being used as a drug intermediate and a synthesizing method of the quinazoline compound. The synthesizing methodhas the advantages that the method is completed through
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- Heterogeneous oxidative synthesis of quinazolines over OMS-2 under ligand-free conditions
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A manganese oxide octahedral molecular sieve (OMS-2) prepared using urea as an additive was found to be an efficient recyclable catalyst for the synthesis of quinazolines via oxidation/cyclization. A broad range of substituted quinazolines were obtained from alcohols and amidines in good yields under ligand-free conditions. OMS-2 was characterized by XRD, BET, ICP-AES, SEM, TEM and XPS, which indicated that the superior catalytic ability might arise from enhanced surface area and crystallinity.
- Li, Bo,Li, Changming,Tian, Liang,Zhou, Jinbo,Huang, Jianfeng,Meng, Xu
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supporting information
p. 15985 - 15989
(2018/10/04)
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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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- Synthesis of Quinazolines via an Iron-Catalyzed Oxidative Amination of N-H Ketimines
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An efficient synthesis of quinazolines based on an iron-catalyzed C(sp3)-H oxidation and intramolecular C-N bond formation using tert-BuOOH as the terminal oxidant is described. The reaction of readily available 2-alkylamino benzonitriles with various organometallic reagents led to 2-alkylamino N-H ketimine species. The FeCl2-catalyzed C(sp3)-H oxidation of the alkyl group employing tert-BuOOH followed by intramolecular C-N bond formation and aromatization afforded a wide variety of 2,4-disubstituted quinazolines in good to excellent yields.
- Chen, Cheng-Yi,He, Fengxian,Tang, Guangrong,Yuan, Huiqing,Li, Ning,Wang, Jinmin,Faessler, Roger
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p. 2395 - 2401
(2018/02/23)
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- Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines
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The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, ha
- Zhu, Jianghe,Shao, Yinlin,Hu, Kun,Qi, Linjun,Cheng, Tianxing,Chen, Jiuxi
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p. 8596 - 8603
(2018/11/27)
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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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- Preparation of 3-hydroxyquinolines from direct oxidation of dihydroquinolinium salts
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A series of functionalized 3,4-dihydroquinolinium salts were prepared from the reaction of aryldiazonium salt with alkene in a nitrile solution. Further oxidation yielding either 3-hydroxyquinoline or quinoline products was investigated. A one-pot process from aryldiazonium salts, alkenes and nitriles leading to 3-hydroxyquinolines was also developed. Furthermore, an intramolecular trapping of an N-arylnitrilium ion with a vinyl group at the ortho position leading to 2-substituted quinolines was revealed.
- Ramanathan, Mani,Wan, Jing,Liu, Shiuh-Tzung
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p. 38166 - 38174
(2018/12/02)
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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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- Design, synthesis and molecular properties prediction of novel quinazoline derivatives as potent antibacterial agents
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A novel series of compounds were synthesized by C-C bond formation of substituted quinazolinones (1) with substituted boronic acids (2) to get 2,4-disubstituted quinazoline (3a-3n) in good to excellent yields. The structures of the new compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral data. An antibacterial and antifungal activity screening results showed that compounds 3b, 3e, 3i and 3l possess excellent activity against Gram (+), Gram (-) bacteria (S. aureus, Klebsiella species, P. aeruginosa) compared to standard drugs. 3l, 3g and 3n showed better antifungal activity against A. nigeri and C. albicans organisms. In this investigation, the target compounds 3a-3n were subjected to in silico molecular properties prediction and drug likeness by employing Molinspiration (Molinspiration, 2014) and MolSoft (MolSoft, 2007) property explorer tool kits for predicting their high oral bioavailability.
- Eswararao,Venkataramireddy,Srinivasareddy,Kumar, Pramod
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p. 1434 - 1440
(2017/05/29)
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- Preparation of Quinazolines via a 2+2+2 Annulation from Aryldiazonium Salts and Nitriles
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A (2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of aryldiazonium salts with two equivalent of nitriles. Reaction of aryldiazonium salt with a nitrile provides the initial formation of a reactive nitrilium ion, which is attacked by another molecule of nitrile followed by electrophilic cyclization to deliver the desired product. Notable flexibility in the substitution patterns, readily available substrates, short reaction time, transition metal-free, and gram-scale synthesis are the advantages of this method.
- Ramanathan, Mani,Liu, Shiuh-Tzung
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p. 8290 - 8295
(2017/08/14)
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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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- General copper-catalyzed coupling of alkyl-, aryl-, and alkynylaluminum reagents with organohalides
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We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under "ligand-free" conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph3Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph3Al with iodoarenes containing p-H, p-Me, p-F, and p-CF3 substituents, which shows a linear curve (R2 = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway.
- Shrestha, Bijay,Thapa, Surendra,Gurung, Santosh K.,Pike, Ryan A. S.,Giri, Ramesh
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p. 787 - 802
(2016/02/18)
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- Csp2-O and C-C Bond Formation via Pd-Catalyzed Coupling Reaction of 2,4-Dichloroquinazoline
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(Chemical Equation Presented) An efficient palladium-catalyzed C-O and subsequent C-C bond formation of 2,4-dichloroquinazoline have been described. The designed strategy results in the synthesis of novel 2-arylated quinazolin-4-ones framework with various aryl/heteroaryl boronic acids in moderate to good yields along with 2,4-diarylated quinazolines. This methodology offers a direct transformation of aryl halides to aryl alcohols/ketone as well as the straight forward application to generate a wide variety of monoaryl and diaryl quinazoline.
- Sharma, Alka,Luxami, Vijay,Paul, Kamaldeep
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p. 241 - 248
(2016/02/10)
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- Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
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An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.
- Ye, Xinglin,Yuan, Jianjun,Zhou, Yirong,Deng, Zhihong,Mao, Xuechun,Peng, Yiyuan
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p. 3976 - 3984
(2016/11/11)
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- Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of N-Sulfinylimines and Benzimidates
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C-H activation of arenes has been established as an important strategy for heterocycle synthesis via annulations between arenes and unsaturated coupling partners. However, nitriles failed to act as such a coupling partner. Dioxazolones have been employed as a synthon of nitriles, and subsequent coupling with arenes such as N-sulfinylimines and benzimidates bearing a functionalizable directing group provided facile access to two classes of quinazolines under Co(III)-catalysis.
- Wang, Fen,Wang, He,Wang, Qiang,Yu, Songjie,Li, Xingwei
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p. 1306 - 1309
(2016/04/01)
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- Heterogeneous Palladium-Catalyzed Hydrogen-Transfer Cyclization of Nitroacetophenones with Benzylamines: Access to C?N Bonds
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The first Pd/C-catalyzed oxidative C(sp3)?H bond amination of o-nitroacetophenones with benzylamines or amino acids proceeding through C?N bond cleavage followed by C?N bond formation by a hydrogen-transfer strategy was developed. These transformations proceeded smoothly in water to afford the desired quinazolines in moderate to good yields. This protocol has a broad substrate scope and good tolerance of air, offers excellent recyclability of the catalyst, and does not need any additional oxidant, ligand, or base; the combination of all of these factors give a new and practical avenue for multiple C?N bond formation. Moreover, a hot filtration experiment indicated that heterogeneous palladium nanoparticles during the reaction are the active species.
- Tang, Lin,Wang, Pengfei,Fan, Yang,Yang, Xingkun,Wan, Changfeng,Zha, Zhenggen
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p. 3565 - 3569
(2016/12/14)
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- Nickel-catalyzed Kumada Cross-coupling Reaction for the Synthesis of 2,4-Diarylquinazolines
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A series of 2,4-diarylquinazolines have been successfully synthesized via the Ni-catalyzed cross-coupling reaction of quinazoline-4-tosylates and aryl Grignard reagents, which provided alternative straightforward approaches for the introduction of aryl groups to quinazolines at C-4 position.
- Ye, Xinglin,Yuan, Zhihan,Zhou, Yirong,Yang, Qin,Xie, Yepeng,Deng, Zhihong,Peng, Yiyuan
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supporting information
p. 1956 - 1962
(2016/11/24)
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- Lewis acid-catalyzed 2-arylquinazoline formation from: N ′-arylbenzimidamides and paraformaldehyde
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An efficient procedure for the synthesis of 2-arylquinazolines from N′-arylbenzimidamides has been developed under transition-metal-free conditions. In this process, stable and low-toxicity paraformaldehyde was used as the carbon source. A broad range of
- Cheng, Xiufang,Wang, Huamin,Xiao, Fuhong,Deng, Guo-Jun
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supporting information
p. 5773 - 5776
(2016/11/06)
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- Quinazoline compounds and preparation method thereof
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The invention discloses quinazoline compounds which have a specific structural formula as shown in the description, wherein R1 is aryl, substituted aryl or alkyl; R2 is fluorine, chlorine or methyl; R3 is aryl, substituted aryl or alkyl. By taking amino a
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Paragraph 0042; 0043
(2016/10/10)
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- Method for synthesizing diphenyl substituted quinazoline compound
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The invention relates to a method for synthesizing a diphenyl substituted quinazoline compound shown as the following formula (III). The method comprises the steps that in a solvent, in the presence of a catalyst, a N-donor ligand, an acid accelerator and alkali, a compound in the following formula (I) and a compound in the following formula (II) react, aftertreatment is carried out after the reaction is finished, and therefore the compound in the formula (III) is obtained. The formula is shown in the description, wherein R1 and R2 are independently selected from H and C1-C6 or C1-C6 alkoxy. According to the method, by means of comprehensive selection and cooperation of a nvoel proper substrate, the catalyst, the N-donor ligand, the acid accelerator, alkali, the solvent and the like, the range of the substrate is widened, the yield is good, and the diphenyl substituted quinazoline compound can be obtained. Therefore, the method has good application prospects and study value in the field of organic chemical synthesis, and the brand new method is provided for synthesis of the compound.
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Paragraph 0075; 0076; 0077; 0078
(2016/10/10)
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- One-pot three-component synthesis of quinazolines: Via a copper-catalysed oxidative amination reaction
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A copper-catalysed three-component reaction for constructing a series of quinazoline derivatives has been developed. In this system, solvents act as the reactants and different functional groups are well tolerated to obtain corresponding products in moderate to good yields.
- Duan, Tiantian,Zhai, Tianran,Liu, Huanhuan,Yan, Zilong,Zhao, Yue,Feng, Lei,Ma, Chen
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p. 6561 - 6567
(2016/07/16)
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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 5
(2016/10/07)
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- A Comparative Investigation: Group 9 Cp?M(III)-Catalyzed Formal [4 + 2] Cycloaddition as an Atom-Economic Approach to Quinazolines
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A comparative study on the catalytic activity of different group 9 [Cp?M(III)] complexes in the formal [4 + 2] cycloaddition of arenes with rarely explored free imines and dioxazolones for the construction of multisubstituted quinazolines is reported herein. This investigation revealed that the cobalt catalyst is uniquely suited to this transformation due to its strong Lewis acidity and high sensitivity to steric hindrance.
- Wang, Xiaoming,Lerchen, Andreas,Glorius, Frank
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supporting information
p. 2090 - 2093
(2016/06/01)
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- Metal-free tandem Beckmann-electrophilic aromatic substitution cascade affording diaryl imines, ketones, amines, and quinazolines
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A cascade reaction sequence involving a Beckmann rearrangement on benzophenone oxime followed by an electrophilic aromatic substitution (EAS) on the intermediate nitrilium ion affords N-phenyl diaryl imines that may then be hydrolyzed to ketones, or reduced to the corresponding amines. Reaction with benzonitrile afforded 2,4-diphenylquinazoline through a Beckmann-Ritter-EAS cascade.
- Sarsah, Samuel R.S.,Lutz, Marlon R.,Bobb, Kailyn Chichi,Becker, Daniel P.
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supporting information
p. 5390 - 5392
(2015/09/15)
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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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supporting information
p. 1216 - 1220
(2015/12/30)
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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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- 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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- 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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- A DMAP-catalyzed mild and efficient synthesis of 1,2-dihydroquinazolines via a one-pot three-component protocol
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An efficient and simple method for the synthesis of 1,2-dihydroquinazolines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) from readily available aromatic or heteroaromatic aldehydes, 2-aminobenzophenone, and ammonium acetate under mild conditions is described. The scope and limitations of the method are discussed.
- Derabli, Chamseddine,Boulcina, Raouf,Kirsch, Gilbert,Carboni, Bertrand,Debache, Abdelmadjid
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supporting information
p. 200 - 204
(2014/01/06)
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- Synthesis of 4-arylquinazolines by arylation of quinazolin-4-ones under mild conditions
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An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields. Georg Thieme Verlag Stuttgart New York.
- Qiu, Guanyinsheng,Huang, Ping,Yang, Qin,Lu, Hui,Xu, Jingshi,Deng, Zhihong,Zhang, Ming,Peng, Yiyuan
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supporting information
p. 3131 - 3136
(2013/12/04)
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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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- Copper(II)-catalyzed three-component cascade annulation of diaryliodoniums, nitriles, and alkynes: A regioselective synthesis of multiply substituted quinolines
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Three become one: Multiply substituted quinolines were synthesized from diaryliodoniums, alkynes, and nitriles by a CuII-catalyzed method. This cascade annulation is highly regioselective, step-economic, flexible with regard to the functional groups, and could potentially be applied to the synthesis of complex molecules. Copyright
- Wang, Yong,Chen, Chao,Peng, Jing,Li, Ming
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supporting information
p. 5323 - 5327
(2013/06/05)
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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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- Efficient aerobic oxidative synthesis of 2-aryl quinazolines via benzyl C-H bond amination catalyzed by 4-hydroxy-TEMPO
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A novel and efficient aerobic protocol for the oxidative synthesis of 2-aryl quinazolines via benzyl C-H bond amination by a one-pot reaction of arylmethanamines with 2-aminobenzoketones and 2-aminobenzaldehydes has been carried out using the 4-hydroxy-TEMPO radical as the catalyst, without any metals or additives.
- Han, Bing,Wang, Chao,Han, Run-Feng,Yu, Wei,Duan, Xiao-Yong,Fang, Ran,Yang, Xiu-Long
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supporting information; experimental part
p. 7818 - 7820
(2011/09/12)
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