- BTP-Rh@g-C3N4 as an efficient recyclable catalyst for dehydrogenation and borrowing hydrogen reactions
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Highly active catalysts play an important role in modern catalysis. A novel and efficient ligand benzotriazole-pyrimidine (BTP) and the corresponding rhodium composite on C3N4 were successfully synthesized. The resulting rhodium composite was fully characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), x-ray diffraction (XRD), thermogravimetric analysis (TGA), and x-ray photoelectron spectroscopy (XPS). The obtained composite exhibited good catalytic activity and good recovery performance in the synthesis of quinoxaline from 2-aminobenzyl alcohol and benzonitrile, and more than 20 quinoxalines were obtained in good yields. Additionally, it also showed that rhodium composite could achieved good catalytic performance in the synthesis of functionalized ketone through borrowing hydrogen strategy.
- Luo, Lan,Liu, Hongqiang,Zeng, Wei,Hu, Wenkang,Wang, Dawei
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- Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation
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Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C-H/N-H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C-H bond of the phenyl ring of the benzylamine.
- Sikari, Rina,Chakraborty, Gargi,Guin, Amit Kumar,Paul, Nanda D.
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p. 279 - 290
(2021/01/09)
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- Efficient synthesis of quinazolines by the iron-catalyzed acceptorless dehydrogenative coupling of (2-aminophenyl)methanols and benzamides
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The acceptorless dehydrogenation coupling (ADC) of (2-aminophenyl)methanols with benzamides was achieved with catalytic FeCl2·4H2O in an efficient synthesis of quinazolines. This simple catalytic system is atom-economical, environmentally benign and suited to a variety of substrates.
- Zhang, Shi-Qi,Cui, Yao,Guo, Bin,Young, David J.,Xu, Ze,Li, Hong-Xi
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- Mixed crystalline phases and catalytic performance of OMS-2 based nanocomposites for one-pot synthesis of quinazolines with O2 as an oxidant
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In this work, a series of sodium phosphotungstate modified manganese oxide octahedral molecular sieve (OMS-2) catalysts ([PW]-OMS-2) were developed, and their catalytic activities were investigated by one-pot synthesis of quinazolines from benzyl alcohol and 2-aminobenzylamine with O2 as green oxidant in dimethyl carbonate (DMC). TEM, XRD and EDS confirmed that sodium phosphotungstate decomposed into phosphotungstic acid and sodium tungstate in the doping process. Meanwhile, phosphotungstic acid attached and located at the surface of OMS-2 and W ions were successfully doped into the OMS-2 framework. For comparison, phosphotungstic acid/OMS-2 was prepared by simple wet impregnation method. The [PW]-OMS-2 is the most highly selective and effective over than phosphotungstic acid/OMS-2 and OMS-2 itself in the one-pot synthesis of quinazolines. It may be due to the synergetic effect of phosphotungstic acid and OMS-2, and successfully doping W into OMS-2 frameworks. Hence, this work provides a new environmentally-friendly and heterogeneous OMS-2 based nanocomposites and it may be put into practice to synthesize heterocyclic compounds.
- Yao, Nan,Bi, Xiuru,Zhang, Liping,Tao, Luyao,Zhao, Peiqing,Meng, Xu,Liu, Xiang
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- Palladium(ii): N, N, O -pincer type complex-mediated dehydrogenative coupling of alcohols to quinazolines
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A new palladium(ii) N,N,O-pincer type complex-promoted one-pot cascade synthesis of quinazolines through the dehydrogenative coupling of easily available alcohols and 2-aminobenzylamine is reported. A distinct set of Pd(ii) complexes (1-2) was synthesized
- Anandaraj, Pennamuthiriyan,Kumaradhas, Poomani,Ramesh, Rengan
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p. 16572 - 16580
(2021/10/01)
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- A cobalt-catalyzed method for synthesizing quinoline and quinazoline compounds
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The present invention discloses a cobalt-catalyzed synthesis of quinoline and quinazoline compounds, by a benzene compound with amino and hydroxyl groups or benzonitrile compounds as raw materials, in the presence of a catalyst and a base by a receptor-fr
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Paragraph 0021; 0064
(2022/01/10)
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- Ruthenium complex and preparation method thereof and catalytic application
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The invention discloses a ruthenium complex and a preparation method thereof and catalytic application. The ruthenium complex is reported for the first time. Research finds that the ruthenium complexhas the activity of catalytically synthesizing quinazoline and derivatives thereof or catalytically synthesizing quinoline and derivatives thereof. When the ruthenium complex provided by the inventionis used for catalytic synthesis of quinazoline and derivatives thereof or quinoline and derivatives thereof, the ruthenium complex has the advantages of mild reaction conditions, wide substrate range, high catalytic product yield and good functional group tolerance, and is significantly superior to the prior art.
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Paragraph 0065-0067; 0072-0073
(2021/01/24)
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- Efficient access to quinolines and quinazolines by ruthenium complexes catalyzed acceptorless dehydrogenative coupling of 2-aminoarylmethanols with ketones and nitriles
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Treatment of N,N,O-tridentate pyrazolyl-pyridinyl-alcohol ligands, 2-(CR1R2OH)-6-[3,5-(R3)2C3HN2]C5H3N (R1 = R2 = Me, R3 = H (L1H); R1 = Me, R2 = Ph, R3 = H (L2H); R1 = R2 = Ph, R3 = H (L3H); R1 = R2 = R3 = Me (L4H)) with RuCl3?xH2O in refluxing EtOH afforded the corresponding Ru(III) complexes L2RuCl (1a-1d), which were well characterized by IR, HR-MS and X-ray single crystal structural determination. These Ru complexes showed similarly high catalytic performance for both dehydrogenative couplings of 2-aminoarylmethanols with ketones and nitriles, giving the quinolines and quinazolines in good to excellent yields. This protocol provides an atom-economical and sustainable route to access various structurally important quinoline and quinazoline derivatives by using phosphine-free ligand based Ru catalysts.
- Feng, Qi,Han, Zhangang,Hao, Zhiqiang,Huo, Shuaicong,Kong, Siqi,Lin, Jin,Lu, Guo-Liang,Zeng, Guang
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- Manganese(I)-Catalyzed Sustainable Synthesis of Quinoxaline and Quinazoline Derivatives with the Liberation of Dihydrogen
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Direct synthesis of N-heterocycles via the acceptorless dehydrogenative coupling is very challenging and scarcely reported under 3d transition-metal catalysis. Here, we have developed an efficient Mn(I)-catalyzed sustainable synthesis of various quinoxalines from 1,2-diaminobenzenes and 1,2-diols via the acceptorless dehydrogenative coupling reaction. Further, this strategy was successfully applied for the unprecedented synthesis of quinazolines by the reaction of 2-aminobenzyl alcohol with primary amides. The present protocol provides an atom-economical and sustainable route for the synthesis of various quinoxaline and quinazoline derivatives by employing an earth-abundant manganese salt and simple phosphine-free NNN-tridentate ligand.
- Mondal, Akash,Sahoo, Manoj Kumar,Subaramanian, Murugan,Balaraman, Ekambaram
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p. 7181 - 7191
(2020/07/21)
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- C?N Cross-Coupling Reactions Under Mild Conditions Using Singlet Di-Radical Nickel(II)-Complexes as Catalyst: N-Arylation and Quinazoline Synthesis
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Herein we report a cost-effective synthetic approach for C?N cross-coupling reactions of a broad array of nitrogen nucleophiles and aryl halides under mild conditions. These reactions are catalyzed by an inexpensive, air-stable, earth-abundant and easy-to-prepare singlet di-radical nickel(II)-catalyst containing two antiferromagnetically coupled single-electron oxidized diiminosemiquinonato type ligands. This protocol provides an alternative method for C?N cross-coupling reactions avoiding nickel(0)/nickel(II) or nickel(I)/nickel(III) redox processes via cooperative participation of metal and ligand-centered redox events. Besides a wide range of N-arylation reactions, by judicious choice of aryl halides and nitrogen nucleophiles the synthesis of a variety of polysubstituted quinazolines has been achieved in moderate to good yields under relatively mild reaction conditions. Our catalyst has been found to be almost equally effective in quinazoline synthesis via C?N cross-coupling of (i) 2-bromobenzylamine with benzamide, and (ii) 2-bromobenzylbromide with amidine. Control experiments and DFT studies were performed to improve the understanding of the cooperative participation of ligand and metal (nickel)-centered redox events during oxidative addition/reductive elimination processes of the catalytic cycle and to shed light on the plausible mechanistic pathway of the C?N cross-coupling reactions. (Figure presented.).
- Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Das, Siuli,van Leest, Nicolaas Petrus,Paul, Nanda D.
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supporting information
p. 4342 - 4353
(2019/08/21)
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- NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines
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An efficient NNN pincer Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism, which underwent alcohol oxidation, nitrile hydration, and cyclocondensation steps. The current protocol is featured with several advantages, such as environmental benignity, operational simplicity, broad substrate scope (compatible with aliphatic nitriles, up to 87% yield), and short reaction time (mostly in 2 h).
- Wan, Xiao-Min,Liu, Zi-Lin,Liu, Wan-Qing,Cao, Xiao-Niu,Zhu, Xinju,Zhao, Xue-Mei,Song, Bing,Hao, Xin-Qi,Liu, Guoji
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p. 2697 - 2705
(2019/04/04)
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- Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
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Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines, 2-aminoquinolines, and quinazolines were synthesized in moderate to good yields from different low-cost and readily accessible starting materials. Several control experiments were carried out to get insight into the reaction mechanism which shows that the nickel and the coordinated diamine ligands participate in a synergistic way during the dehydrogenation of alcohols.
- Chakraborty, Gargi,Sikari, Rina,Das, Siuli,Mondal, Rakesh,Sinha, Suman,Banerjee, Seemika,Paul, Nanda D.
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p. 2626 - 2641
(2019/02/26)
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- Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex
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A sustainable synthesis of quinazoline and 2-aminoquinoline via acceptorless dehydrogenative annulation is presented. The reaction is catalyzed by earth-abundant well-defined manganese complexes bearing NNS ligands. Furthermore, a one-pot synthetic strate
- Das, Kalicharan,Mondal, Avijit,Pal, Debjyoti,Srimani, Dipankar
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supporting information
p. 3223 - 3227
(2019/05/10)
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- An easy access towards quinazolines via an improved protocol for ynones
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A simple and convenient method has been developed to accomplish Pt/2,2'-bipyridyl catalyzed acyl Sonagashira coupling for the efficient synthesis of ynones. The reaction display significant tolerance to various functional groups and the methodology has be
- Ghosh, Subhadeep,Das, Asish R.
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p. 1249 - 1258
(2020/06/27)
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- Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling
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Two environmentally benign methods for the synthesis of quinazolines via acceptorless dehydrogenative coupling of 2-aminobenzylamine with benzyl alcohol (Path A) and 2-aminobenzylalcohol with benzonitrile (Path B), catalyzed by cheap, earth abundant and easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism and to establish the acceptorless dehydrogenative nature of the catalytic reactions.
- Parua, Seuli,Sikari, Rina,Sinha, Suman,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
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p. 11154 - 11166
(2018/09/06)
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- A facile and versatile protocol for the one-pot PhI(OAc)2 mediated divergent synthesis of quinazolines from 2-aminobenzylamine
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In this present work iodobenzenediacetate (PIDA) has been found to be the key reagent in absence or presence of catalytic amount of molecular iodine (I2)/zinc chloride (ZnCl2) to construct quinazoline scaffold from 2-aminobenzylamine and a variety of easily available aldehydes, aryl and aliphatic amines, aliphatic and aryl alcohols and nitriles. This protocol provides mild and robust conditions along with great versatility to synthesize 2-substituted quinazolines from diverse starting materials in good to excellent yields. The developed protocol is also well applicable to reactants containing ease to oxidation prone functional groups.
- Saha, Moumita,Mukherjee, Prasun,Das, Asish R.
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supporting information
p. 2044 - 2049
(2017/05/04)
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- Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air
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By using air as the superior oxidant, a highly atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted quinolines starting from methyl ketones instead of nitriles.
- Yao, Song,Zhou, Kaijing,Wang, Jiabing,Cao, Hongen,Yu, Lei,Wu, Jianzhang,Qiu, Peihong,Xu, Qing
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supporting information
p. 2945 - 2951
(2017/07/24)
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- ABNO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted 4H-3,1-Benzoxazines and Quinazolines
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A new transition-metal-free 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO) catalyzed aerobic oxidative synthesis of 2-substituted 4H-3,1-benzoxazines and quinazolines has been developed through cascade reaction of aldehydes with 2-aminobenzyl alcohols and 2-amino
- Ma, Jiaqi,Wan, Yan,Hong, Chao,Li, Meichao,Hu, Xinquan,Mo, Weimin,Hu, Baoxiang,Sun, Nan,Jin, Liqun,Shen, Zhenlu
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p. 3335 - 3342
(2017/06/29)
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- Synthesis method for 2-substituted quinazoline heterocyclic compound
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The invention discloses a synthesis method for a 2-substituted quinazoline heterocyclic compound. According to the efficient synthesis method, 2-aminobenzylalcohol and nitrile are subjected to an oxidation-cyclization reaction in air under the alkaline condition to prepare the 2-substituted quinazoline heterocyclic compound. By means of the method, no transition metal catalyst or ligand is needed, and the reaction is directly carried out through heating under the alkaline condition to obtain the 2-substituted quinazoline heterocyclic compound. The reaction condition is simple, operation is easy, air serves as an economical, safe and environment-friendly catalyst, a by-product is water, and atom efficiency is high. The requirement of the method for the reaction condition is low, and the method has certain research and industrial application prospects.
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Paragraph 0029; 0030; 0031; 0032
(2016/12/22)
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- Magnesium iodide-catalyzed synthesis of 2-substituted quinazolines using molecular oxygen and visible light
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A novel and efficient approach for the synthesis of quinazolines by aerobic photooxidation with an iodine reagent at room temperature is reported. This method uses harmless visible light from compact fluorescent lamps and molecular oxygen as the sole oxid
- Yamaguchi,Sakairi,Yamaguchi,Tada,Itoh
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p. 56892 - 56895
(2016/07/07)
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- Assembly of 4H-chromenes, imidazobenzothiazines and quinazolines via copper-catalyzed domino reactions using 2-halobenzyl tosylates as substrates
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The use of 2-halobenzyl tosylates as substrates in copper-catalyzed domino intermolecular substitution/intramolecular arylation processes for the efficient and selective preparation of heterocycles is reported for the first time. Reaction of 2-halobenzyl tosylates with β-ketoesters delivers 4H-chromenes with yields ranging between 59 and 89%. Imidazobenzothiazines are formed with yields up to 82% upon reaction of 2-halobenzyl tosylates with 2-mercaptoimidazoles. When 2-halobenzyl tosylates are reacted with benzamidines the corresponding quinazolines are obtained.
- Omar, Mohamed A.,Conrad, Jürgen,Beifuss, Uwe
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p. 5682 - 5695
(2015/03/30)
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- Palladium-catalyzed one pot 2-arylquinazoline formation via hydrogen-transfer strategy
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The palladium catalytic system was first applied to 2-arylquinazoline synthesis via hydrogen transfer methodology. Various (E)-2-nitrobenzaldehyde O-methyl oximes reacted easily with alcohols or benzyl amines to provide N-heterocyclic compounds in good to
- Wang, Huamin,Chen, Hui,Chen, Ya,Deng, Guo-Jun
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p. 7792 - 7799
(2014/12/10)
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- Synthesis of quinazolines and tetrahydroquinazolines: Copper-catalyzed tandem reactions of 2-bromobenzyl bromides with aldehydes and aqueous ammonia or amines
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An efficient synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or amines has been developed. By using ammonia and simple aliphatic amines as the nitrogen source, the present method provides a versatile and practical protocol for the synthesis of quinazolines and 1,2,3,4-tetrahydroquinazolines. Copper on the beat: An efficient, simple and economical synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines has been developed through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or simple aliphatic amines. Copyright
- Fan, Xuesen,Li, Bin,Guo, Shenghai,Wang, Yuanyuan,Zhang, Xinying
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supporting information
p. 739 - 743
(2014/03/21)
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- Synthesis of 2-substituted quinazolines via iridium catalysis
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An iridium-catalyzed hydrogen transfer reaction was successfully applied in the synthesis of 2-substituted quinazolines in moderate yields starting from aldehydes or alcohols with 2-aminobenzylamines.
- Fang, Jie,Zhou, Jianguang,Fang, Zhijie
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p. 334 - 336
(2013/03/28)
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- Mild and efficient ligand-free copper-catalyzed condensation for the synthesis of quinazolines
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Condensation of o-iodobenzaldehydes 1a_c with amidine hydrochlorides 2a_p under ligand-free copper-catalyzed Ullmann N-arylation conditions afforded the corresponding quinazolines 3a-r in good to excellent yields.
- Truong, Vouy Linh,Morrow, Michelle
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scheme or table
p. 758 - 760
(2010/04/05)
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