- 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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- From Methaqualone and Beyond: Structure - Activity Relationship of 6-, 7-, and 8-Substituted 2,3-Diphenyl-quinazolin-4(3H)-ones and in Silico Prediction of Putative Binding Modes of Quinazolin-4(3H)-ones as Positive Allosteric Modulators of GABAA
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Methaqualone (2-methyl-3-(o-tolyl)-quinazolin-4(3H)-one, MTQ) is a moderately potent positive allosteric modulator (PAM) of GABAA receptors (GABAARs). In a previous structure-activity relationship (SAR) study probing the importance of 2- and 3-substituent
- Wang, Peng-Fei,Jensen, Anders A.,Bunch, Lennart
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p. 4362 - 4375
(2020/11/30)
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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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- Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran
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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.
- Hao, Wenyan,Xu, Zhaotao,Zhou, Zebiao,Cai, Mingzhong
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p. 8522 - 8532
(2020/07/16)
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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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- 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro analogs from substituted anthranilic acids and orthoesters
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A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substitutedanthranilic acidswithorthoesters inethanol catalyzedby acetic acid. Additionally,wehave also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.
- Annor-Gyamfi, Joel K.,Bunce, Richard A.
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- Design, synthesis and pharmacological evaluation of 2-phenyl quinazolin-4-one derivatives as anticolorectal cancer and anti-inflammatory agent
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Quinazoline derivatives are heterocyclic compounds that acts as important structural lead for the discovery of effective therapeutic agents. The anti-inflammatory activity along with cytotoxicity helps to reduce the inflammation and pain associated with carcinoma. Derivatives of quinazoline-4-one were preliminary screened and in silico molecular modelling studies using Autodock were performed. In the docking study, ligands were docked against anticancer and anti-inflammatory targets. In silico analysis revealed that the compounds with aromatic substitution at 3rd and halogen substitution at 6th or 7th positions possess lesser side effects and have more potent antitumor activity. Based upon these results 12 compounds were selected, synthesized, characterized and screened for their in vitro, anti-inflammatory, antioxidant and anticancer activities. From the in vitro studies, compounds QA4, QA7 and QB1 showed good anticancer, anti-inflammatory and antioxidant activity when compared to the standard.
- Bosco, Deena,Balakrishnan, Ashitha,Mishra, Rohan,Aneesh
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p. 2677 - 2685
(2018/11/20)
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- Design, Synthesis, and Pharmacological Characterization of N-(4-(2 (6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)yl)ethyl)phenyl)quinazolin-4-amine Derivatives: Novel Inhibitors Reversing P-Glycoprotein-Mediated Multidrug Resistance
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P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a principal obstacle for successful cancer chemotherapy. A novel P-gp inhibitor with a quinazoline scaffold, 12k, was considered to be the most promising for in-depth study. 12k possessed high potency (EC50 = 57.9 ± 3.5 nM), low cytotoxicity, and long duration of activity in reversing doxorubicin (DOX) resistance in K562/A02 cells. 12k also boosted the potency of other MDR-related cytotoxic agents with different structures, increased accumulation of DOX, blocked P-gp-mediated Rh123 efflux, and suppressed P-gp ATPase activity in K562/A02 MDR cells. However, 12k did not have any effects on CYP3A4 activity or P-gp expression. In particular, 12k had a good half-life and oral bioavailability and displayed no influence on DOX metabolism to obviate the side effects closely related to increased plasma concentrations of cytotoxic agents in vivo.
- Qiu, Qianqian,Liu, Baomin,Cui, Jian,Li, Zheng,Deng, Xin,Qiang, Hao,Li, Jieming,Liao, Chen,Zhang, Bo,Shi, Wei,Pan, Miaobo,Huang, Wenlong,Qian, Hai
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supporting information
p. 3289 - 3302
(2017/05/05)
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- Design and synthesis of quinazolinones as EGFR inhibitors to overcome EGFR resistance obstacle
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The epidermal growth factor receptor (EGFR) T790M mutant is found in about 50% of clinically acquired resistance to gefitinib among patients with non-small cell lung cancer (NSCLC). New derivatives of 4(3H)-quinazolinones were synthesized and evaluated for their inhibitory activity against NSCLC. The results of the study demonstrated that compound 79, 7-chloro-3-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-2-phenylquinazolin-4(3H)-one was found to be the most potent compounds of the series with IC50 value of 0.031?μM against mutant T790M/L858R EGFR. Compounds 15, 51, 73, 75, 78, 79 and 96 were less potent against A549 (WT EGFR and k-Ras mutation) and HT-29 (non-special gene type) cells, showing a high safety index. The obtained results showed that compounds 15, 51, 73, 75, 78, 79 and 96 could be the promising template to overcome drug resistance mediated by the EGFR T790 Mutant.
- Patel, Harun M.,Pawara, Rahul,Ansari, Azim,Noolvi, Malleshappa,Surana, Sanjay
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p. 2713 - 2723
(2017/04/17)
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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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- Direct oxidative cascade cyclisation of 2-aminobenzoic acid and arylaldehydes to aryl 4H-3,1-benzoxazin-4-ones with oxone
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This paper presents a methodology of oxidative cascade cyclisation of 2-aminobenzoic acids and arylaldehyde using I2as a catalyst and an environmentally benign oxidant oxone. This method displays facile access to a diverse range of substituted aryl 4H-3,1-benzoxazin-4-ones. This synthetic methodology has many advantages such as: (1) easy availability of starting material, (2) transition metal-free condition (3) use of an environmentally benign oxidant.
- Munusamy, Sathishkumar,Muralidharan, Vivek Panyam,Iyer, Sathiyanarayanan Kulathu
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supporting information
p. 520 - 523
(2017/01/16)
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- RETRACTED ARTICLE: Palladium-Catalyzed Decarboxylative Selective Acylation of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with α-Oxo Carboxylic acids via Preferential Cyclic Imine-N-Directed Aryl C-H Activation
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The benzoxazine scaffolds are of much interest as they are found in a large array of natural products and pharmaceutical drugs with diverse activities. We have developed a palladium-catalyzed decarboxylative selective mono- and bis-acylation of 4H-benzo[d
- Majhi, Biju,Kundu, Debasish,Ghosh, Tubai,Ranu, Brindaban C.
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p. 283 - 295
(2016/02/16)
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- Anti-convulsant potential of quinazolinones
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A series of novel quinazoline derivatives were synthesized, virtually screened through different filters and evaluated for their anticonvulsant activity against electrically and chemically induced seizures, compared with that of the standard drugs methaqualone and sodium valproate. Compound 48, 3-(2-aminophenyl)-7-chloro-2-phenylquinazolin-4(3H)-one, was found to be the most potent compound of the series accompanied by relatively low neurotoxicity and low toxicity in the median lethal dose test as compared with the reference drugs. The obtained results showed that compounds 12, 48, 49 and 50 could be useful templates for future design, optimization, and investigation to construct more active analogs.
- Patel, Harun M.,Noolvi, Malleshappa N.,Shirkhedkar, Atul A.,Kulkarni, Abhijeet D.,Pardeshi, Chandrakantsing V.,Surana, Sanjay J.
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p. 44435 - 44455
(2016/06/09)
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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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- Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source
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Various cyclic carbonyl compounds were concisely synthesized by carbonylative cyclization of haloarenes bearing nucleophilic moieties under Pd catalysis. A broad substrate scope and a feasible large-scale synthesis clearly demonstrate the high applicability of the reaction as a general, user-friendly method for access to cyclic carbonyl compounds.
- Konishi, Hideyuki,Nagase, Hiroki,Manabe, Kei
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supporting information
p. 1854 - 1857
(2015/01/30)
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- Copper catalyzed C-N bond formation/C-H activation: Synthesis of aryl 4H-3,1-benzoxazin-4-ones
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We have developed a practical and efficient synthesis of 2-phenyl-4H-benzo[d][1,3]oxazine-4-one derivatives through copper catalyzed tandem reaction of 2-iodobenzoic acid with arylmethanamines under aerobic conditions. Compared to the literature methods toward the synthesis of 2-phenyl-4H-benzo[d][1,3]oxazine-4-one, the synthetic method reported in this Letter has broad substrate scope, mild reaction condition, and uses an inexpensive catalyst.
- Munusamy, Sathishkumar,Venkatesan, Sathesh,Sathiyanarayanan, Kulathu Iyer
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p. 203 - 205
(2015/02/02)
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- Synthesis and characterization of quinazoline derivatives: Search for hybrid molecule as diuretic and antihypertensive agents
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To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derive
- Rahman, Mujeeb Ur,Rathore, Ankita,Siddiqui, Anees A.,Parveen, Gazala,Yar, M. Shahar
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p. 733 - 743
(2014/12/11)
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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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- One-pot approach to 2-arylbenzoxazinone derivatives from 2-alkynylanilines using copper-mediated tandem reactions
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In this study, we describe a one-pot method to obtain a variety of 2-arylbenzoxazinones and N-benzoyl anthranilic acid by using a copper catalyst and molecular oxygen as oxidants. This protocol involves tandem cyclization and oxidative processes of 2-alkynylanilines to afford significant motifs in synthetic and medicinal chemistry with moderate yields. We also demonstrated that combining the Sonogashira coupling and the developed method realized the synthesis of 2-arylbenzoxazinones derivatives from commercially available 2-iodoanilines and terminal acetylenes.
- Yamashita, Mitsuaki,Iida, Akira
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p. 5746 - 5751
(2015/03/30)
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- [bmIm]OH: An efficient basic catalyst for the synthesis of 4H-benzo[d][1,3-]oxazin-4-one derivatives in solvent-free conditions
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Reusable [bmIm]OH was found to be a highly efficient renewable homogenous catalyst for the rapid and convenient synthesis of benzoxazine-4-one derivatives from o-iodobenzoic-acid and benzonitrile at 75 °C in moderate to good yields. This methodology provides a facile and straightforward path to construct other related heterocycles in an eco-compatible fashion.
- Waseem, Malik Abdul,Shireen,Srivastava, Anjali,Srivastava, Arjita,Rahila,Siddiqui
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supporting information
p. 6072 - 6076
(2015/01/08)
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- Copper-mediated oxidative tandem reactions with molecular oxygen: Synthesis of 2-arylbenzoxazinone derivatives from indoles
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We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl an
- Yamashita, Mitsuaki,Iida, Akira
-
supporting information
p. 2991 - 2993
(2014/05/06)
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- Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
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A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
- Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 8196 - 8198
(2013/09/12)
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- Copper-catalyzed C-N bond formation/rearrangement sequence: Synthesis of 4H-3,1-benzoxazin-4-ones
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A facile and efficient copper-catalyzed method for the synthesis of 4H-3,1-benzoxazin-4-one derivatives has been developed. This procedure is based on a tandem intramolecular C-N coupling/rearrangement process. This method would provide a new and useful strategy for construction of N-heterocycles.
- Ge, Zhi-Yuan,Xu, Qiong-Ming,Fei, Xi'Ang-Dong,Tang, Ting,Zhu, Yong-Ming,Ji, Shun-Jun
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p. 4524 - 4529
(2013/06/05)
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- 7-chloro-3-(substituted benzylidene/phenyl ethylidene amino)-2- phenylquinazolin-4(3H)-ones: Synthesis, antimicrobial and antitubercular evaluation
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In this study, a series of 7-chloro-3-(substituted benzylidene/phenyl ethylidene amino)-2-phenyl quinazolin- 4(3H)-ones (1-10) were prepared and evaluated for antitubercular activity against Mycobacterium tuberculosis (MTB). The antitubercular screening results indicated that 7-chloro-3-(4- (dimethylamino)benzylidene amino)-2- phenylquinazolin-4(3H)-one (10) was the most potent one (MIC = 0.78 × 10-3 μM) and exhibited activity equivalent to the standard compound isoniazid (MIC = 0.80 × 10-3 μM). Further, the synthesized compounds were tested for their antibacterial activity against Gram positive and Gram negative bacteria. The comparison of antibacterial and antimycobacterial results indicated that different structural requirements are necessary for a compound to be effective against bacterial and mycobacterial targets.
- Anand, Rajarathinam Vijai,Narasimhan, Balasubramanian,Chandran, Ramachandran Vasanthakumari Pradeep,Jayaveera, Koralakundata Narsimha
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p. 2831 - 2836,6
(2020/07/30)
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- Phl(OAc)2-mediated one-pot synthesis of benzoxazinones from anthranilic acids and aromatic aldehydes
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A novel way to synthesise 2-aryl-4H-benzo[d][1,3]oxazin-4-ones has been developed by the cyclisation of Schiff bases with (diacetoxyiodo)benzene. The salient features of this new protocol which starts from an anthranilic acid and an aromatic aldehyde, are
- Xie, Yuanyuan,Wang, Suping
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p. 123 - 126
(2012/09/22)
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- Synthesis, antimicrobial activity and application of some novel quinazolinone based monoazo reactive dyes on various fibres
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The main target of this paper was to synthesize novel reactive dyes that not only give good dyeing property but also show pharmacological activity i.e. antimicrobial activity (antibacterial and antifungal). In this regard ten novel monoazo quinazolinone based reactive dyes (7a-j) were made by coupling of diazotised 3-{4-[4-amino-2-nitrobenzyl]-3-nitrophenyl}-7-chloro-2- phenylquinazolin-4(3H)-one (4) with various p-chloro anilino cyanurated coupling components (6a-j). The structures of all these synthesized dyes were confirmed by elemental analysis and spectral methods. The antimicrobial activity, colorimetric data, solvent effect and fastness properties of these dyes were also investigated.
- Patel, Divyesh R.,Patel, Keshav C.
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experimental part
p. 1 - 10
(2011/12/02)
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- Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents
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In our effort to identify potent gastric sparing anti-inflammatory agents, a series of methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl quinazolinones were designed by analogue-based design strategy and synthesized for biological evaluation. Subsequ
- Manivannan,Chaturvedi
-
scheme or table
p. 4520 - 4528
(2011/09/19)
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- Synthesis of quinoline-based thieno-seleno-phenylquinazolinones
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The synthesis of quinoline-substituted phenylquinazolinones containing sulfur and selenium is described. These molecules were isolated from a series of reactions of 2-phenyl-4H-3,1-benzoxazin-4-one with 2-chloro, 2-thieno, and 2-selenoquinoline-3-carbalde
- Prakash Naik,Bhojya Naik,Ravikumar Naik,Raghavendra,Aravinda,Lamani
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scheme or table
p. 460 - 470
(2009/11/30)
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- 1H and 13C NMR spectral studies of some 4H-3,1-benzoxazin-4-ones and their 2-acylaminobenzoic acid precursors
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The 1H and 13C NMR spectra of twelve 4H-3,1-benzoxazine-4-ones and of their acylaminobenzoic acid precursors are presented. Differentiation between these two series of compounds is best achieved through the characteristic JCH coupling interactions in the high frequency carbonyl region. Some 4H-pyrido[2,3-d][1,3]oxazin-4-ones have also been studied and some earlier literature assignments revised.
- Osborne, Alan G.,Goolamali, Zia
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p. 1079 - 1100
(2007/10/03)
-