- Rhodium(III)-catalyzed [4?+?2] annulation of N-arylbenzamidines with 1,4,2-dioxazol-5-ones: Easy access to 4-aminoquinazolines via highly selective C[sbnd]H bond activation
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A novel approach for the synthesis of 4-aminoquinazolines has been developed via rhodium(III)-catalyzed [4 + 2] annulation of N-arylbenzamidines with 1,4,2-dioxazol-5-ones. This reaction features excellent regioselectivity, broad substrate scope and high step economy, which would provide the reference for the construction of the fused 4-aminoquinazolines with biologically and pharmacologically active compounds.
- Ren, Jie,Huang, Yanzhen,Pi, Chao,Cui, Xiuling,Wu, Yangjie
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p. 2592 - 2596
(2021/03/09)
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- Application of Aza-type iso-cryptolepine derivatives in prevention and treatment of agricultural plant diseases
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The invention discloses application of any compound of Aza-type iso-cryptolepine derivatives A0-A38 in prevention and treatment or resisting of agricultural plant diseases. Antibacterial activity testresults show that the compounds have certain inhibitory
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Paragraph 0034-0039
(2020/11/25)
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- Rh(III)-Catalyzed One-Pot Synthesis of Benzimidazoquinazolines via C-H Amidation-Cyclization of N-LG-2-phenylbenzoimidazoles
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An efficient protocol to synthesize substituted benzo[4,5]imidazo[1,2-c]quinazolines starting from N-LG-2-phenylbenzoimidazole and dioxazolones catalyzed by Rh(III) or Ir(III) has been developed. Various substituted benzo[4,5]imidazo[1,2-c]quinazolines co
- Xu, Linhua,Li, Tingfang,Wang, Lianhui,Cui, Xiuling
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p. 560 - 567
(2018/12/11)
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- Design, synthesis and antifungal activity evaluation of isocryptolepine derivatives
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In this paper, the nitrogen atom was inserted into the anthracycline system of the isocryptolepine nucleus to obtain the “Aza”-type structure benzo[4,5]imidazo[1,2-c] quinazoline. A series of “Aza”-type derivatives were designed, synthesized and evaluated for their antifungal activity against six plant fungi in vitro. Among all derivatives, compounds A-0, B-1 and B-2 showed significant antifungal activity against B. cinerea with the EC50 values of 2.72 μg/mL, 5.90 μg/mL and 4.00 μg/mL, respectively. Compound A-2 had the highest activity against M. oryzae with the EC50 values of 8.81 μg/mL, and compound A-1 demonstrated the most control efficacy against R. solani (EC50, 6.27 μg/mL). Moreover, compound A-0 was selected to investigate the in vivo tests against B. cinerea and the results indicated that the preventative efficacy of it up to 72.80% at 100 μg/mL. Preliminary mechanism studies revealed that after treatment with A-0 at 5 μg/mL, the B. cinerea mycelia appeared curved, collapsed and the cell membrane integrity may be damaged. The reactive oxygen species production, mitochondrial membrane potential and nuclear morphometry of mycelia have been changed, and the membrane function and cell proliferation of mycelia were destroyed. Compounds A-0, A-1, B-1 and B-2 presented weaker toxicities against two cells lines than isocryptolepine. This study lays the foundation for the future development of isocryptolepine derivatives as environmentally friendly and safe agricultural fungicides.
- Li, Jun-cai,Wang, Ren-xuan,Sun, Yu,Zhu, Jia-kai,Hu, Guan-fang,Wang, Yu-ling,Zhou, Rui,Zhao, Zhong-min,Liu, Ying-qian,Peng, Jing-wen,Yan, Yin-fang,Shang, Xiao-fei
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supporting information
(2019/09/30)
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- Synthetic method of benzimidazole [1,2-c] quinazolines compound
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The invention belongs to the technical field of synthesis of compounds, and particularly relates to a synthetic method of a benzimidazole [1,2-c] quinazolines compound. The synthetic method of the benzimidazole [1,2-c] quinazolines compound comprises the following steps: under the condition of alkalinity, assisting in copper to catalyzing 2-(2-halo phenyl) benzimidazole and primary amine at firstby using ultraviolet light to carry out Uhlmann coupling reaction; and then carrying out oxidized ring closure and oxidized dehydrogenation by using oxygen as an oxidizing agent to form the benzimidazole [1,2-c] quinazolines compound. The method is carried out at a room temperature, wherein the molar ratio of 2-(2-halo phenyl) benzimidazole, alkali and amine is 1: 3: (1-3), and the use amount of acopper catalyst is 20 mmol%. Iodobenzene with high activity is used in photocatalyzed Uhlmann N-arylation of aryl halide in the prior art, moreover, reports for carbon-hydrogen bond ammonium oxide are finished under the condition of heating, and furthermore, benzylamines are used. Photocatalyzed Uhlmann N-arylation of aryl chloride and aryl fluoride is broken through; and moreover, carbon-hydrogen bond oxidation and amination reaction of photocatalyzed non-benzylamine aliphatic amines are also broken through.
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Paragraph 0021-0041
(2018/10/19)
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- Rh-Catalyzed Annulation of ortho-C?H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines
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A Rh-catalyzed unique and direct approach for constructing a series of 5-arylimidazo[1,2-c]quinazolines in moderate to excellent yields from simple and readily available 2-arylimidazoles and 3-phenyl-1,4,2-dioxazol-5-ones was described. This procedure pro
- Wu, Xiaopeng,Sun, Song,Xu, Shengbo,Cheng, Jiang
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p. 1111 - 1115
(2018/01/27)
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- Amidinyl Radical Formation through Anodic N?H Bond Cleavage and Its Application in Aromatic C?H Bond Functionalization
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We report herein an atom-economical and sustainable approach to access amidinyl radical intermediates through the anodic cleavage of N?H bonds. The resulting nitrogen-centered radicals undergo cyclizations with (hetero)arenes, followed by rearomatization,
- Zhao, Huai-Bo,Hou, Zhong-Wei,Liu, Zhan-Jiang,Zhou, Ze-Feng,Song, Jinshuai,Xu, Hai-Chao
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p. 587 - 590
(2017/01/07)
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- Copper-mediated aerobic oxidative synthesis of benzimidazo fused quinazolines via a multicomponent approach
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The first copper mediated aerobic oxidative multi-component synthesis of benzimidazo[1,2-c]quinazolines has been developed from 2-(2-halophenyl)benzoimidazoles, aldehydes and sodium azide as a nitrogen source. This protocol involves the formation of three
- Rai, Byanju,Kumar, Promod,Kumar, Atul
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p. 85915 - 85918
(2015/11/03)
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- General and efficient copper-catalyzed aerobic oxidative synthesis of N-fused heterocycles using amino acids as the nitrogen source
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A general and efficient copper-catalyzed aerobic oxidative method for the synthesis of N-fused heterocycles has been developed by using readily available α-amino acids as the nitrogen source. The reactions underwent N-arylation, aerobic oxidative dehydrogenation, intramolecular cyclization and dissociation of formic acid. This method should provide a general and practical strategy for the construction of N-fused heterocycles.
- Liu, Qing,Yang, Haijun,Jiang, Yuyang,Zhao, Yufen,Fu, Hua
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p. 15636 - 15644
(2013/09/12)
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- Copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination: A convenient route to indolo[1,2-c]quinazoline derivatives
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An efficient synthesis of indolo[1,2-c]quinazoline derivatives has been developed by copper-catalyzed sequential Ullmann N-arylation and aerobic oxidative C-H amination. The protocol uses readily available 2-(2-halophenyl)-1H-indoles and (aryl)methanamines as the starting materials to afford indolo[1,2-c]quinazolines, which are the core units of hinckdentine A.
- Sang, Peng,Xie, Yongju,Zou, Jianwei,Zhang, Yuhong
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supporting information; experimental part
p. 3894 - 3897
(2012/09/21)
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- Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
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A convenient and efficient copper-catalyzed cascade method has been developed for the synthesis of benzimidazoquinazoline derivatives via reactions of readily available substituted 2-(2-halophenyl)benzoimidazoles with amidines or guanidine under mild conditions (even at room temperature).
- Xu, Shan,Lu, Juyou,Fu, Hua
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p. 5596 - 5598
(2011/06/21)
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- Mono and bis-6-arylbenzimidazo[1,2-c]quinazolines: A new class of antimicrobial agents
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With the aim of obtaining novel biologically active compounds, we have synthesized a series of mono, bis-2-o-arylideneaminophenylbenzimidazoles and a second series of corresponding mono, bis-6-arylbenzimidazo[1,2-c]quinazolines respectively. The target be
- Rohini, Rondla,Shanker, Kanne,Reddy, Puchakayala Muralidhar,Ho, Yen-Peng,Ravinder, Vadde
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experimental part
p. 3330 - 3339
(2009/12/01)
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- Solvent-Free Synthesis of 6-Arylbenzimidazo[1,2-c]quinazolines under Microwave Irradiation
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The syntheses of 2-(2-nitrophenyl)-1-benzoyl-1H-benzimidazole derivatives 5-9 and their reduction to the corresponding 2-benzimidazoylbenzamides 10-13 are described. Compounds 10-13 were cleanly and efficiently converted to the corresponding 6-arylbenzimi
- Pessoa-Mahana, Hernan,Pessoa-Mahana, C. David,Salazar, Ricardo,Valderrama, Jaime A.,Saez, Edmundo,Araya-Maturana, Ramiro
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p. 436 - 440
(2007/10/03)
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- Azlactones in heterocyclic synthesis: Part IV - A new route for the synthesis of 6-substituted and 6-arylidene-benzimidazo-[1,2-c]quinazolines
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Condensation of 2-(o-aminophenyl) benzimidazole 1 with 4- arylidene-2-substituted oxazolin-5-ones 2 (azlactones) in acetic acid results in the formation of 5,6-dihydro-6-arylidene-benzimidazo[1,2-c]quinazolines 3 and 6-substituted benzimidazo[1,2-c]quinazolines 4. Structures of these compounds have been established based on their spectral data, and direct comparison with authentic samples prepared by unambiguous routes.
- Prameela Subhashini,Hanumanthu
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p. 430 - 432
(2007/10/03)
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- A facile synthesis of 6-substituted benzimidazo[1,2-c]quinazolines under microwave irradiation
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Microwave irradiation promoted the high-yield cyclocondensation of ortho esters (1a-f) with 2-(2-aminophenyl)benzimidazole (2), as the catalyst was no longer needed.
- Khajavi, Mohammad S.,Rad-Moghadam, Kurosh,Hazarkhani, Hasan
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p. 2617 - 2624
(2007/10/03)
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- Synthesis of benzimidazo[1,2-c]quinazolines as possible bronchodilators
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Synthesis of some 6-aryl-benzimidazo[1,2-c]quinazolines 4 have been critically investigated. The first method, based on the condensation of substituted-1,3-benzoxazin-4-(3H)-one 2 with o-phenylenediamine followed by cyclization of the resulting 2-aryl-3-(
- Rao, A. Raghu Ram,Bahekar, Rajesh H.
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p. 434 - 439
(2007/10/03)
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- Reaction of Benzylamine with o-Substituted Nitrobenzenes: Synthesis of Benzimidazole and Qiunazoline Derivatives
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The utility of the reaction of benzylamine with o-substituted nitrobenzenes for the synthesis of heterocyclic compounds has been explored. 2-Substituted and 1,2-disubstituted benzimidazoles have been obtained by reacting o-nitroanilines and N-substituted o-nitroanilines with benzylamine.Two quinazolinone derivates and two tetracyclic compounds have also been prepared by the reaction of benzylamine with appropriate o-substituted nitrobenzenes.A suitable mechanism has been suggested for the formation of the products.
- Rao, C. V. Chalapathi,Reddy, K. Kondal,Rao, N. V. Subba
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p. 655 - 658
(2007/10/02)
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