- Mn(iii)-mediated cascade cyclization of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids: Construction of quinazoline derivatives
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A novel and efficient Mn(iii)-mediated oxidative radical cascade reaction of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids is reported. The single electron oxidation of a commercially available organo boronic acid in the presence of a mild oxidant, Mn(OAc)3·2H2O, resulted in moderate yields of the corresponding quinazoline derivatives.
- Kumar, Gujjenahalli Ramalingaiah Yogesh,Begum, Noor Shahina
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p. 9811 - 9817
(2021/06/15)
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- Vinylene carbonate: Beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines
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In this paper, we developed a rhodium-catalyzed annulation of vinylene carbonate with amidines, leading to 4-methylquinazolines with moderate to excellent yields. This procedure proceeded by sequentialortho-acylation and annulation, where vinylene carbonate served as the acetylation reagent rather than the ethyne surrogate.
- Wang, Chang,Fan, Xiaodong,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
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supporting information
p. 3929 - 3932
(2021/04/26)
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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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- Hydrogen peroxide-mediated synthesis of 2,4-substituted quinazolines: Via one-pot three-component reactions under metal-free conditions
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An efficient metal-free synthesis of 2,4-substituted quinazolines via a hydrogen peroxide-mediated one-pot three-component reaction of 2-aminoaryl ketones, aldehydes, and ammonium acetate has been developed. The transformation proceeded readily under mild conditions in the presence of commercially available hydrogen peroxide. The significant advantages of this approach are (1) the readily available atom-efficient and green hydrogen peroxide as oxidant; (2) no transition metal catalyst is required; (3) mild reaction conditions; and (4) wide substrate scope. To the best of our knowledge, utilizing hydrogen peroxide as an atom-efficient and green oxidant for the synthesis of 2,4-substituted quinazolines has not previously been reported in the literature. This method is complementary to previous protocols for the synthesis of 2,4-substituted quinazolines. This journal is
- Nguyen, Khang X.,Nguyen, Tung T.,Pham, Phuc H.,Phan, Anh N. Q.,Phan, Nam T. S.,Trinh, Khang H.
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p. 29900 - 29909
(2020/10/06)
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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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- 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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- Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines
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The in situ formed ruthenium catalytic system ([Ru]/L) was found to be highly selective for the dehydrogenative coupling reaction of 2-aminophenyl ketones with amines to form quinazoline products. The deaminative coupling reaction of 2-aminobenzamides with amines led to the efficient formation of quinazolinone products. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming any toxic byproducts.
- Kirinde Arachchige, Pandula T.,Yi, Chae S.
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supporting information
(2019/05/08)
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- Maximizing the Catalytic Activity of Nanoparticles through Monolayer Assembly on Nitrogen-Doped Graphene
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We report a facile method for assembly of a monolayer array of nitrogen-doped graphene (NG) and nanoparticles (NPs) and the subsequent transfer of two layers onto a solid substrate (S). Using 3 nm NiPd NPs as an example, we demonstrate that NiPd-NG-Si (Si=silicon wafer) can function as a catalyst and show maximum NiPd catalysis for the hydrolysis of ammonia borane (H3NBH3, AB) with a turnover frequency (TOF) of 4896.8 h?1 and an activation energy (Ea) of 18.8 kJ mol?1. The NiPd-NG-S catalyst is also highly active for catalyzing the transfer hydrogenation from AB to nitro compounds, leading to the green synthesis of quinazolines in water. Our assembly method can be extended to other graphene and NP catalyst materials, providing a new 2D NP catalyst platform for catalyzing multiple reactions in one pot with maximum efficiency.
- Yu, Chao,Guo, Xuefeng,Shen, Mengqi,Shen, Bo,Muzzio, Michelle,Yin, Zhouyang,Li, Qing,Xi, Zheng,Li, Junrui,Seto, Christopher T.,Sun, Shouheng
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supporting information
p. 451 - 455
(2018/02/21)
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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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- 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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- AgPd Nanoparticles Deposited on WO2.72 Nanorods as an Efficient Catalyst for One-Pot Conversion of Nitrophenol/Nitroacetophenone into Benzoxazole/Quinazoline
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We report a seed-mediated growth of 2.3 nm AgPd nanoparticles (NPs) in the presence of 40 × 5 nm WO2.72 nanorods (NRs) for the synthesis of AgPd/WO2.72 composites. The strong interactions between AgPd NPs and WO2.72 NRs make the composites, especially the Ag48Pd52/WO2.72, catalytically active for dehydrogenation of formic acid (TOF = 1718 h-1 and Ea = 31 kJ/mol) and one-pot reactions of formic acid, 2-nitrophenol, and aldehydes into benzoxazoles in near quantitative yields under mild conditions. The catalysis can also be extended to the one-pot reactions of ammonium formate, 2-nitroacetophenone, and aldehyde for high yield syntheses of quinazolines. Our studies demonstrate a new catalyst design to achieve a green chemistry approach to one-pot reactions for the syntheses of benzoxazoles and quinazolines.
- Yu, Chao,Guo, Xuefeng,Xi, Zheng,Muzzio, Michelle,Yin, Zhouyang,Shen, Bo,Li, Junrui,Seto, Christopher T.,Sun, Shouheng
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supporting information
p. 5712 - 5715
(2017/05/04)
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- Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: Synthesis of quinazolines by trapping of ammonia
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A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylideneb
- Gopalaiah, Kovuru,Saini, Anupama,Devi, Alka
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p. 5781 - 5789
(2017/07/22)
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- Ultrasound-Assisted Preparation of Copper(I) Oxide Nanocubes: High Catalytic Activity in the Synthesis of Quinazolines
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A facile and green ultrasound-assisted synthesis of Cu2O nanocubes at room temperature is presented. The Cu2O nanocubes were characterized using XRD, SEM, TEM, energy-dispersive X-ray spectroscopy, UV/Vis spectroscopy, differential scanning calorimetry with thermogravimetric analysis, and FTIR spectroscopy. The Cu2O nanocubes were employed as a heterogeneous nanocatalyst and were found to be highly active in the preparation of quinazolines by the tandem cyclization of 2-bromobenzaldehydes with amidines under ligand-free conditions. Various quinazolines could be prepared in excellent yields within a very short reaction time. Furthermore, the Cu2O nanocatalyst could be recycled and reused up to four times without any significant loss of catalytic activity.
- Raut, Amol B.,Tiwari, Abhishek R.,Bhanage, Bhalchandra M.
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p. 1292 - 1297
(2017/04/14)
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- Rh(III)- and Zn(II)-Catalyzed Synthesis of Quinazoline N-Oxides via C-H Amidation-Cyclization of Oximes
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Quinazoline N-oxides have been prepared from simple ketoximes and 1,4,2-dioxazol-5-ones via Rh(III)-catalyzed C-H activation-amidation of the ketoximes and subsequent Zn(II)-catalyzed cyclization. The substrate scope and functional group compatibility were examined. The reaction features relay catalysis by Rh(III) and Zn(II).
- Wang, Qiang,Wang, Fen,Yang, Xifa,Zhou, Xukai,Li, Xingwei
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p. 6144 - 6147
(2016/12/09)
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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
- -
-
Paragraph 0028; 0029
(2016/10/10)
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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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- 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 12; 13
(2016/10/07)
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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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- 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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- A Sc(OTf)3-catalyzed cascade reaction of o-aminoacetophenone with methanamine: Construction of dibenzo[b,h][1,6]naphthyridine derivatives
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An unexpected Sc(OTf)3-catalyzed and air-mediated cascade reaction of o-aminoacetophenones with methanamines was discovered as an efficient synthetic approach to a novel class of fluorescent fused-four-ring dibenzo[b,h][1,6]naphthyridine derivatives. Two possible mechanisms of the reaction were proposed. The photophysical properties of the dibenzo[b,h][1,6]naphthyridine 1a were initially considered. This journal is
- Mao, Dan,Tang, Jun,Wang, Wenbo,Liu, Xin,Wu, Shengying,Yu, Jianjun,Wang, Limin
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supporting information
p. 2122 - 2128
(2015/03/05)
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- One-pot synthesis of 2-arylquinazolines and tetracyclic isoindolo[1,2-a]quinazolines via cyanation followed by rearrangement of ortho-substituted 2-halo-N-arylbenzamides
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The one-pot synthesis of substituted 2-arylquinazoline derivatives and tetracylic isoindolo[1,2-a]quinazoline via cyanation followed by rearrangement of ortho-substituted 2-halo-N-arylbenzamides is described. Using dimethyl sulfoxide (DMSO) as the solvent
- Gawande, Sachin D.,Zanwar, Manoj R.,Kavala, Veerababurao,Kuo, Chun-Wei,Rajawinslin,Yao, Ching-Fa
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p. 168 - 176
(2015/01/30)
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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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- N-Bu4NI-catalyzed selective dual amination of sp3 C-H bonds: Oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale
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An n-Bu4NI catalyzed domino reaction that involves selective dual amination of sp3 C-H bonds has been developed. The protocol affords a facile and efficient approach to the synthesis of imidazo[1,5-c] quinazolines under mild conditions.
- Zhao, Dan,Wang, Teng,Shen, Qi,Li, Jian-Xin
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supporting information
p. 4302 - 4304
(2014/04/17)
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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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- Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions
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An efficient and selective Pd(0)-catalyzed sp3 C-H bond arylation-oxidation of 4-methylquinazolines is reported. The method enables the introduction of arylketone at the benzylic position of 4-methylquinazolines without the use of an additional directing group, and atmospheric oxygen is used as the sole oxidant.
- Zhao, Dan,Zhu, Min-Xue,Wang, Yue,Shen, Qi,Li, Jian-Xin
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supporting information
p. 6246 - 6249
(2013/09/23)
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- Visible light-mediated synthesis of quinazolines from 1,2- dihydroquinazoline 3-oxides
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A series of quinazolines were synthesized in good to excellent yields by exposing 1,2-dihydroquinazoline 3-oxides to visible light in acetonitrile without the presence of any external sensitizers. The only exception was the 2-(p-nitrophenyl)-substituted s
- Chen, Yi-Chou,Yang, Ding-Yah
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p. 10438 - 10444
(2013/11/19)
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- Copper-catalyzed three-component one-pot synthesis of quinazolines
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Two efficient approaches to multi-substituted quinazolines by the three-component one-pot reaction of o-bromo aromatic ketones/aldehydes, ammonia water and aromatic aldehydes, or primary alcohols catalyzed by CuCl have been developed.
- Ju, Jia,Hua, Ruimao,Su, Ji
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p. 9364 - 9370
(2012/11/07)
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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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- 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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- 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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- An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives
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A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2).
- Alonso, Rafael,Caballero, Alegría,Campos, Pedro J.,Sampedro, Diego,Rodríguez, Miguel A.
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experimental part
p. 4469 - 4473
(2010/07/08)
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- Direct synthesis of quinazolines through copper-catalyzed reaction of aniline-derived benzamidines
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A novel synthesis of 2-phenyl-4-[(triisopropylsilyl)methyl]quinazolines from monosubstituted arenes has been developed. Treatment of N-phenylbenzamidines with 5-nitro-1-[(triisopropylsilyl)ethynyl]-1,2- benziodoxol-3(1H)-one and K2CO3 in the presence of a catalytic amount of CuBr in benzene gives 2-phenyl-4-[(triisopropylsilyl)methyl] quinazolines in moderate to good yields.
- Ohta, Yusuke,Tokimizu, Yusuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
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supporting information; experimental part
p. 3963 - 3965
(2010/11/17)
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- Microwave-promoted syntheses of quinazolines and dihydroquinazolines from 2-aminoarylalkanone O-phenyl oximes
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(Chemical Equation Presented) A wide range of biologically active compounds contain the quinazoline ring system. A new free-radical-based method of making functionalized quinazolines is described, which relies on microwave-promoted reactions of O-phenyl oximes with aldehydes. A small set of 2-aminoaryl alkanone O-phenyl oximes was prepared and shown to produce dihydroquinazolines when mixed with an aldehyde in toluene and subjected to microwave heating. When ZnCl2 was included in the reaction mixture, fully aromatic quinazolines were produced in high yields by a rapid and convenient process. The method worked well with alkyl, aryl, and heterocyclic aldehydes and for a variety of substituents in the benzenic part of the molecule. Similar reactions employing ketones instead of aldehydes were less efficient. Although some dihydroquinazolines did form, they were accompanied by several byproducts. Surprisingly, in each case, one of the byproducts was a quinoline derivative, and a plausible mechanism to account for this rearrangement is proposed.
- Portela-Cubillo, Fernando,Scott, Jackie S.,Walton, John C.
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supporting information; experimental part
p. 4934 - 4942
(2009/12/01)
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- REGIOSELECTIVE ADDITIONS OF GRIGNARD AND LITHIUM REAGENTS TO 2-BENZONITRILE AND 2-BENZONITRILE
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Phenylmagnesium bromide and methylmagnesium bromide in tetrahydrofuran undergo a regioselective addition to the cyano group of the two title compounds.Phenyllithium and methyllithium add selectively to the azomethine portion of 2-benzo
- Strekowski, L.,Cegla, M. T.,Harden, D. B.,Mokrosz, J. L.,Mokrosz, M. J.
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p. 4265 - 4268
(2007/10/02)
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