22312-62-5Relevant academic research and scientific papers
Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
Liu, Mingzhu,Wei, Yu,Xu, Liang
supporting information, (2021/10/06)
Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.
N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
, p. 16848 - 16857 (2021/12/06)
N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
Synthesis and biological evaluation of novel benodanil-heterocyclic carboxamide hybrids as a potential succinate dehydrogenase inhibitors
Hou, Taiping,Jiang, Mingfang,Jin, Hong,Tao, Ke,Wan, Jun,Yang, Jian,Zhao, Yongtian
, (2020/10/02)
In order to discover new antifungal agents, twenty novel benodanil-heterocyclic carboxamide hybrids were designed, synthesized, and characterized by 1H NMR and HRMS. In vitro, their antifungal activities against four phytopathogenic fungi were
One-Pot, Multistep Reactions for the Modular Synthesis of N, N′-Diarylindazol-3-ones
Liu, Shuai,Xu, Liang,Wei, Yu
, p. 1596 - 1604 (2019/02/07)
The pot-economic synthesis of N,N′-diarylindazol-3-ones has been developed using readily available isatoic anhydrides, aryl amines, and aryl boronic acids. A Cu-catalyzed oxidative C-N cross-coupling and dehydrogenative N-N formation sequence under an air atmosphere affords indazol-3-one derivatives in good to excellent yields. Such process merges well with the preceding decarboxylative amination reaction, resulting in a more modular and straightforward approach.
Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
, p. 9201 - 9209 (2018/07/13)
A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
Bollenbach, Maud,Aquino, Pedro G. V.,de Araújo-Júnior, Jo?o Xavier,Bourguignon, Jean-Jacques,Bihel, Frédéric,Salomé, Christophe,Wagner, Patrick,Schmitt, Martine
supporting information, p. 13676 - 13683 (2017/10/10)
A simple, sustainable, efficient, mild, and low-cost protocol was developed for d-glucose-assisted Cu-catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen-containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because the reaction proceeds in aqueous media, occurs at or near ambient temperature, and provides the N-arylated products in good to high yields.
Identification of potent orally active factor Xa inhibitors based on conjugation strategy and application of predictable fragment recommender system
Ishihara, Tsukasa,Koga, Yuji,Iwatsuki, Yoshiyuki,Hirayama, Fukushi
, p. 277 - 289 (2015/02/05)
Anticoagulant agents have emerged as a promising class of therapeutic drugs for the treatment and prevention of arterial and venous thrombosis. We investigated a series of novel orally active factor Xa inhibitors designed using our previously reported conjugation strategy to boost oral anticoagulant effect. Structural optimization of anthranilamide derivative 3 as a lead compound with installation of phenolic hydroxyl group and extensive exploration of the P1 binding element led to the identification of 5-chloro-N-(5-chloro-2-pyridyl)-3-hydroxy-2-{[4-(4-methyl-1,4-diazepan-1-yl)benzoyl]amino}benzamide (33, AS1468240) as a potent factor Xa inhibitor with significant oral anticoagulant activity. We also reported a newly developed Free-Wilson-like fragment recommender system based on the integration of R-group decomposition with collaborative filtering for the structural optimization process.
Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
, p. 4736 - 4742 (2015/05/13)
A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
Zhao, Dan,Wang, Teng,Li, Jian-Xin
supporting information, p. 6471 - 6474 (2014/06/09)
A novel metal-free synthesis of quinazolinones via dual amination of sp3 C-H bonds was developed. The sp3 carbon in methylarenes or adjacent to a heteroatom in DMSO, DMF or DMA was used as the one carbon synthon. This journal is the Partner Organisations 2014.
Synthesis, antimicrobial evaluation, ot-QSAR and mt-QSAR studies of 2-amino benzoic acid derivatives
Mahiwal, Kuldeep,Kumar, Pradeep,Narasimhan, Balasubramanian
experimental part, p. 293 - 307 (2012/09/07)
A series of 2-amino benzoic acid derivatives (1-28) were synthesized and evaluated for their in vitro antimicrobial activity against the panel of Gram positive, Gram negative bacterial and fungal strains. The results of antimicrobial studies indicated that, in general, the synthesized compounds were found to be bacteriostatic and fungistatic in action. QSAR studies performed by the development of one target and multi target models indicated that multi-target model was effective in describing the antimicrobial activity as well demonstrated the effect of structural parameters viz. LUMO, 3χv and W on antimicrobial activity of 2-amino benzoic acid derivatives. Springer Science+Business Media, LLC 2010.
