18600-54-9Relevant articles and documents
Design, synthesis and anticonvulsant evaluation of N-[(substituted 1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one derivatives
Kumar, Sachin,Jha,Tripathi, Rati K.P.,Yar, M. Shahar
, p. 1375 - 1379 (2017)
A series of quinazolinone derivatives (7a-7e) have been designed, synthesized and evaluated for the anticonvulsant activity using maximal electroshock seizure (MES) model. The compound 3-[(5-(4-chloro)phenyl-4,5-dihydro-1H-pyrazol-3-yl)amino]-2-(4-methylphenyl)quinazolin-4(3H)-one (7c) was found to be most active compound showing 85.23 % protection and was found to be nonneurotoxic up to 4 h. This study indicates that the quinazolinone based derivatives could be further exploited for the discovery of newer and more effective anticonvulsant agents.
Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
, p. 1263 - 1266 (2020/10/08)
A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran
Hao, Wenyan,Xu, Zhaotao,Zhou, Zebiao,Cai, Mingzhong
, p. 8522 - 8532 (2020/07/16)
A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst, yielding a wide variety of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in good to excellent yields. This supported palladium catalyst could be facilely obtained by a two-step procedure from easily available starting materials and readily recovered via a simple filtration process and recycled at least 8 times without any apparent decrease in catalytic efficiency. The developed methodology not only avoids the use of toxic solvents such as tetrahydrofuran and dimethylformamide but also solves the basic problem of expensive palladium catalyst recovery and reuse and prevents effectively palladium contamination of the desired product.
Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
Cai, Mingzhong,Huang, Bin,Xu, Zhaotao,Zhou, Zebiao
, p. 581 - 590 (2020/02/13)
A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N, N -diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional group tolerance, good to high yields, and easy recyclability of the palladium catalyst. The reaction is the first example of heterogeneous palladium-catalyzed carbonylative coupling for the preparation of diverse 2-arylbenzoxazinones from commercially easily available 2-iodoanilines and aryl iodides.
Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
supporting information, (2020/02/15)
Palladium (0)-catalyzed Ortho-benzoxylation of the sp2 C–H bond of arylbenzoxazinones with carboxylic acid is reported. With benzoxazinone as directing group, the reaction went smoothly under the benign condition and gave the desired product wi
Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
Panja, Subir,Maity, Srabani,Majhi, Biju,Ranu, Brindaban C.
, p. 5777 - 5786 (2019/08/30)
A palladium-catalyzed chelation-assisted selective ortho C-H bond olefination of biologically active 4H-benzo[d][1,3] oxazin-4-one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio- and stereose
ANTI-ULCERATIVE COLITIS COMPOUND
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Paragraph 0021, (2018/05/17)
Anti-ulcerative colitis compounds include quinazoline derivatives having the following structural formula: wherein R is H, OH, or OCH3, R1 is OH or OCH3, and R2 is OCH3, or a pharmaceutically acceptab
Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
supporting information, p. 3527 - 3530 (2018/06/26)
A variety of 2-aminobenzonitriles were prepared from 2-arylindoles in good to excellent yields through tert-butylnitrite (TBN)-mediated nitrosation and sequential iron(III)-catalyzed C-C Bond cleavage in a one-pot fashion. The 2-aminobenzonitriles can be used to rapidly synthesize benzoxazinones by intramolecular condensation. The present method features an inexpensive iron(III) catalyst, gram scalable preparations, and novel C-C bond cleavage of indoles.
One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant
Shang, Xian-Xing,Vu, Huu-Manh,Li, Xu-Qin
supporting information, p. 377 - 383 (2017/10/30)
A series of synthetically interesting 2-arylbenzoxazinones was prepared from 2-arylindoles by an efficient oxidative reaction mediated by (diacetoxyiodo)benzene [PhI(OAc) 2 ] and assisted by water. PhI(OAc) 2 was used as the sole oxi
Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones
Dabiri, Minoo,Farajinia Lehi, Noushin,Kazemi Movahed, Siyavash,Khavasi, Hamid Reza
supporting information, p. 6264 - 6268 (2017/08/02)
A Pd-catalyzed ortho-selective halogenation of benzoxazinone and quinazolinone scaffolds has been described employing N-halosuccinimide as both a halogen source and an oxidant reagent via C-H bond activation. This transformation shows high chemo- and regioselectivities and demonstrates a broad range of benzoxazinone and quinazolinone substrates with different functional groups and has been scaled up to the gram level.