- The synthesis of a novel series of substituted 2-phenyl-4H-3,1- benzoxazin-4-ones
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Following initial studies on a substituted 2-[3-methylphenyl]-4H-3,1- benzoxazin-4-one showing some cytotoxic activity, the synthesis of a novel series of 2-phenyl substituted 4H-3,1-benzoxazin-4-ones is reported herein.
- Pavlidis,Perry
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- Quinazolinone derivatives as orally available ghrelin receptor antagonists for the treatment of diabetes and obesity
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The peptide hormone ghrelin is the endogenous ligand for the type 1a growth hormone secretagogue receptor (GHS-R1a) and the only currently known circulating appetite stimulant. GHS-R1a antagonism has therefore been proposed as a potential approach for obe
- Rudolph, Joachim,Esler, William P.,O'Connor, Stephen,Coish, Philip D. G.,Wickens, Philip L.,Brands, Michael,Bierer, Donald E.,Bloomquist, Brian T.,Bondar, Georgiy,Chen, Libing,Chuang, Chih-Yuan,Claus, Thomas H.,Fathi, Zahra,Fu, Wenlang,Khire, Uday R.,Kristie, James A.,Liu, Xiao-Gao,Lowe, Derek B.,McClure, Andrea C.,Michels, Martin,Ortiz, Astrid A.,Ramsden, Philip D.,Schoenleber, Robert W.,Shelekhin, Tatiana E.,Vakalopoulos, Alexandras,Tang, Weifeng,Wang, Lei,Yi, Lin,Gardell, Stephen J.,Livingston, James N.,Sweet, Laurel J.,Bullock, William H.
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- Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
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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.
- Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
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p. 1263 - 1266
(2020/10/08)
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- Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
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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.
- Cai, Mingzhong,Huang, Bin,Xu, Zhaotao,Zhou, Zebiao
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p. 581 - 590
(2020/02/13)
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- One-step synthesis of 4H-3,1-benzoxazin-4-ones from Weinreb amides and 1,4,2-dioxazol-5-ones via cobalt-catalyzed C-H bond activation
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A one-step synthesis of 4H-3,1-benzoxazin-4-ones from readily available Weinreb amides and 1,4,2-dioxazol-5-ones under Cp*Co(III) catalysis is described. The reactions proceeded in moderate to good yields with high functional group compatibility.
- Tanimoto, Iku,Kawai, Kentaro,Sato, Akane,Yoshino, Tatsuhiko,Matsunaga, Shigeki
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p. 118 - 125
(2019/07/31)
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- 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
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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
- Panja, Subir,Maity, Srabani,Majhi, Biju,Ranu, Brindaban C.
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p. 5777 - 5786
(2019/08/30)
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- Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C-C Bond Cleavage of 2-Arylindoles
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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.
- Chen, Wei-Li,Wu, Si-Yi,Mo, Xue-Ling,Wei, Liu-Xu,Liang, Cui,Mo, Dong-Liang
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p. 3527 - 3530
(2018/06/26)
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- Silver and Palladium Cocatalyzed Carbonylative Activation of Benzotriazoles to Benzoxazinones under Neutral Conditions
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A novel and efficient method for the carbonylative activation of benzotriazoles to benzoxazinones has been developed. By using a silver and palladium bimetallic catalyst system, a broad range of benzotriazoles were transformed into the corresponding benzoxazinones in moderate to good yields with excellent functional group tolerance. Notably, this procedure proceeds under neutral conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 6232 - 6235
(2017/11/24)
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- Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones
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A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp3)-C(sp2) bond employing iodine, sodium bicarbonate, and tbutyl hydroperoxide in DMSO at 95 °C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.
- Verma, Ajay,Kumar, Sangit
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p. 4388 - 4391
(2016/10/11)
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- Copper-Catalyzed C–N, C–O Coupling Reaction of Arylglyoxylic Acids with Isatins
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The copper(II)-catalyzed decarboxylative coupling reactions of arylglyoxylic acids with isatins afford 4H-benzo[d][1,3]oxazin-4-ones via decarbonylation and concurrent C–N, C–O bond formation. (Figure presented.).
- Prakash, Rashmi,Gogoi, Sanjib
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supporting information
p. 3046 - 3049
(2016/10/09)
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- Catalytic aza-wittig reaction of acid anhydride for the synthesis of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones
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Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.
- Wang, Long,Xie, Yi-Bi,Huang, Nian-Yu,Yan, Jia-Ying,Hu, Wei-Min,Liu, Ming-Guo,Ding, Ming-Wu
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p. 4010 - 4016
(2016/07/06)
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- 2-BENZOYLAMINOBENZAMIDE DERIVATIVES AS BCL-3 INHIBITORS
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The invention relates to a compound of general formula (I): wherein R1, R2, R3, R4, Q, m and n are as defined herein. The compounds are inhibitors of Bcl3 and are useful for the treatment of cancer, particularly
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Page/Page column 30
(2015/02/25)
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- Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors
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Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.
- Khan, Zulfiqar Ali,Afzal, Noshaba,Hussain, Zaib,Naqvi, Syed Ali Raza,Bari, Ayesha,Shahzad, Sohail Anjum,Yar, Muhammad,Mahmood, Nasir,Bukhari, Shazia Anwer,Mansha, Asim,Zahoor, Ameer Fawad,Khan, Abdur Rahman,Ahmad, Matloob
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p. 4561 - 4565
(2014/12/10)
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- Pd-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones: Synthesis of fluorescent indazolo[3,2-b]quinazolinones
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A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechani
- Yang, Weiguang,Chen, Jiuxi,Huang, Xiaobo,Ding, Jinchang,Liu, Miaochang,Wu, Huayue
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supporting information
p. 5418 - 5421
(2015/02/19)
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- Synthesis of some new glutamine linked 2,3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents
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A series of novel glutamine linked 2,3-disubstituted quinazolinone conjugates was synthesized from methyl anthranilate and different substituted acids and acid chlorides. The compounds 5a-l were prepared in good yields. All compounds were screened for their antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against Candida albicans and Aspergillus flavus using paper disk diffusion technique. The minimum inhibitory concentrations of the compounds were also determined by agar streak dilution method. The compound 5b was found to exhibit the most potent in vitro anti-microbial activity. When tested for their antioxidant activity, compounds 5i and 5l showed potent radical scavenging activity, while compound 5g had moderate effect against 2,2-diphenyl-1-picrylhydrazyl, hydroxyl, nitric oxide, and superoxide radical scavenging assays. These results suggest that, the three quinazolinone analogs (5g, 5i, and 5l) could be considered as useful templates for future development to obtain more potent antioxidant agents.
- Prashanth,Revanasiddappa
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p. 2665 - 2676
(2013/07/26)
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- Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones
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The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.
- Hussain, Zaib,Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Yar, Muhammad,Hussain, Abdullah Ijaz,Chatha, Shahzad Ali Shahid,Mahmood, Nasir,Khan, Khalid Mohammed
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p. 449 - 455
(2013/07/27)
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- Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones
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Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.
- Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Mahmood, Nasir,Yar, Muhammad,Zahoor, Ameer Fawad
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p. 152 - 156
(2013/02/22)
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- A convenient and general palladium-catalyzed carbonylative coupling for the synthesis of 2-arylbenzoxazinones
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CO and CO again: A new double carbonylation methodology for the synthesis of 2-arylbenzoxazinones has been developed (see scheme). Copyright
- Wu, Xiao-Feng,Schranck, Johannes,Neumann, Helfried,Beller, Matthias
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supporting information; experimental part
p. 12246 - 12249
(2011/12/02)
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- N,N-Dimethylchlorosulfitemethaniminium chloride as a dehydrating agent - An efficient one-pot synthesis of 1,3,4-oxadiazoles and 4H-3,1-benzoxazin-4-ones
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Aroylhydrazines (3) on treatment with carboxylic acids (1) in the presence of N,N-dimethylchlorosulfitemethaniminium chloride (2) yields directly 1,3,4-oxadiazoles (4).Reaction between anthranilic acid (6) and carboxylic acids (5) in the presence of 2 affords 4H-3,1-benzoxazin-4-ones (7).
- Sain, Bir,Sandhu, Jagir S
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p. 768 - 770
(2007/10/02)
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- A SIMPLE PREPARATION OF 2-ARYL-4H-3,1-BENZOXAZIN-4-ONES
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Room temperature treatment of methyl N-acylanthranilates with concentrated sulfuric acid leads to 2-aryl-4h-3,1-benzoxazin-4-ones in excellent yield.
- Papadopoulos, Eleftherios P.,Torres, Catherine D.
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p. 1039 - 1042
(2007/10/02)
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