- Synthesis and Reactions of Some New Quinazoline Derivatives for In Vitro Evaluation as Anticancer and Antimicrobial Agents
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A novel series of N,O,S heterocyclic compounds incorporated at position-3 of a quinazolin-4(3H)-one moiety were synthesized through a p-phenloxy binding including oxadiazolethione pyridazinetrione, thiazolidinedione, benzothiazindione, and quinazolinedione. New carbamates, urea derivatives, and Mannich bases were also prepared for the purpose of in vitro anticancer cell lines evaluation and cytotoxic activity. The key intermediate 2-(4-chlorophenyl)-3-(4-hydroxyphenyl)quinazolin-4(3H)-one was prepared from the reaction of 4H-benzo [d][3,1]oxazin-4-one and a nitrogenous nucleophilic compound, 4-aminophenol. Some of the newly synthesized compounds showed significant cytotoxic activity.
- Gouhar, Rasha S.,Kamel, Mohsen M.
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- Synthesis and Anticancer Evaluation of Some Novel Quinazolin-4(3H)-one Derivatives
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A new series of quinazolinone derivatives bearing pyridine, pyrimidine, pyrazole, or pyran moieties were synthesized for the purpose of anticancer cell line evaluation. Synthesis of these derivatives was achieved by the reaction of the ketone 2 with the appropriate aldehydes in the presence of either ethylcyanoacetate or malononitrile and ammonium acetate in one-pot reaction. Chalcones 6 reacted also with hydrazine hydrate to give the corresponding pyrazolines 7 and reacted with urea or thiourea to give the 2-oxopyrimidines or the 2-thioxopyrimidines 8, respectively. Evaluation of some representative examples of the newly synthesized compounds against cancer cell lines showed promising activity as anticancer agents.
- Gouhar, Rasha S.,Haneen, David S. A.,El-Hallouty, Salwa M.
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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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- 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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- Quinazolinone-schiff's base hybrids as phosphodiesterase 4b inhibitors with dual activity against COPD and lung cancer
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A series of thirty compounds of quinazolinone-Schiff's base hybrids were rationally designed, synthesized, and evaluated for their in vitro Phosphodiesterase 4B inhibition, anti-lung and anti-colon cancer activities. Compounds 9, 16, 23, 29, 30, 31, 32 an
- Mansour, Mostafa A.,El-Saadi, Mohamed T.,Amin, Noha H.,Canzoneri, Joshua C.,Keeton, Adam B.,Piazza, Gary A.,Abdel-Rahman, Hamdy M.
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p. 4851 - 4866
(2020/12/25)
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- Domino synthesis of pyrimido and imidazoquinazolinones
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A simple method for the synthesis of N-alkyl-2-arylquinazolin-4-amines, methyl 4-((2-arylquinazolin-4-yl)amino) butanoates, 6-aryl-2,3-dihydro-4H-pyrimido[1,2-c]quinazolin-4-ones, and 5-arylimidazo[1,2-c]quinazolin-3(2H)-ones has been described. It involves a simple reaction of N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides with alkylamine, γ-aminobutyric acid, β-alanine, l-alanine, and glycine methyl esters hydrochloride in acetonitrile to afford the desired compounds after a series of instantaneous reactions that include Dimroth rearrangement. The reaction involves reflux for 12 hours, simple addition of reagents to an in situ generated benzimidoyl chloride, and simple workup, to form 21 examples of pure compounds in high yields. The active intermediate N-(2-cyanophenyl)-substitutedbenzimidoyl chlorides were formed by the reaction of N-(2-cyanophenyl)-substitutedbenzamides with thionyl chloride in a one-pot strategy. The alternative method described for this preparation deals with an exhausting multistep reactions starting from anthranilic acid.
- Fathalla, Walid,Nofal, Eman Y.,El-Moneim, Mohamed Abd
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p. 1266 - 1274
(2020/01/21)
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- Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
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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
- Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
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supporting information
(2020/02/15)
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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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- Thermo-Promoted Reactions of Anthranils with Carboxylic Acids, Amines, Phenols, and Malononitrile under Catalyst-Free Conditions
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A convenient and atom-economical procedure for the thermo-promoted reactions of anthranil with different substrates was developed. The catalyst-free process affords various useful building blocks with good to moderate yields. This chemistry enables several step- and cost-effective approaches for biologically interesting molecules and provides an efficient platform for the investigation of untapped reactions at high temperature.
- Jiang, Jing,Cai, Xin,Hu, Yanwei,Liu, Xuejun,Chen, Xiaodong,Wang, Shun-Yi,Zhang, Yinan,Zhang, Shilei
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p. 2022 - 2031
(2019/05/16)
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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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- One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant
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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
- Shang, Xian-Xing,Vu, Huu-Manh,Li, Xu-Qin
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supporting information
p. 377 - 383
(2017/10/30)
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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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- Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid
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The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre
- Bharathimohan, Kuppusamy,Ponpandian, Thanasekaran,Jafar, Ahamed A.
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p. 2806 - 2813
(2017/05/29)
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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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- Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine
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A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and
- Pattarawarapan, Mookda,Wet-Osot, Sirawit,Yamano, Dolnapa,Phakhodee, Wong
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p. 589 - 592
(2017/03/11)
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- Pd-Catalyzed regioselective C-H halogenation of quinazolinones and benzoxazinones
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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.
- Dabiri, Minoo,Farajinia Lehi, Noushin,Kazemi Movahed, Siyavash,Khavasi, Hamid Reza
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supporting information
p. 6264 - 6268
(2017/08/02)
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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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- 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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- TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones
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The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.
- Yu, Junchao,Zhang-Negrerie, Daisy,Du, Yunfei
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p. 562 - 568
(2016/02/18)
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- Synthesis, antiphospholipase A2, antiprotease, antibacterial evaluation and molecular docking analysis of certain novel hydrazones
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Some novel hydrazone derivatives 6a-o were synthesized from the key intermediate 4-Chloro-N-(2-hydrazinocarbonyl-phenyl)-benzamide 5 and characterized using IR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis. The inhibitor
- El-Sayed, Nahed N. E.,Alafeefy, Ahmed M.,Bakht, Mohammed A.,Masand, Vijay H.,Aldalbahi, Ali,Chen, Nan,Fan, Chunhai,Bacha, Abir Ben
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- BCL-3 INHIBITORS
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The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.
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Paragraph 000366; 000367; 000368; 000373; 000374
(2016/04/06)
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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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- Carbonylative synthesis of phthalimides and benzoxazinones by using phenyl formate as a carbon monoxide source
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A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source. The present catalytic protocol circumvents the use of an expensive phosphine ligand as well as solvent in the case of the phthalimide synthesis. Moreover, mild reaction conditions and a tolerance of various functional groups enhance the general applicability of this method.
- Chavan, Sujit P.,Bhanage, Bhalchandra M.
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p. 2405 - 2410
(2015/04/22)
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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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- Benzenesulfonamides incorporating bulky aromatic/heterocyclic tails with potent carbonic anhydrase inhibitory activity
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Three series of sulfonamides incorporating long, bulky tails were obtained by applying synthetic strategies in which substituted anthranilic acids, quinazolines and aromatic sulfonamides have been used as starting materials. They incorporate long, bulky diamide-, 4-oxoquinazoline-3-yl- or quinazoline-4-yl moieties in their molecules, and were investigated for the inhibition of four physiologically relevant carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic human (h) hCA I and II, as well as the transmembrane hCA IX and XII. Most of the new sulfonamides showed excellent inhibitory effects against the four isoforms, with KIs of 7.6-322 nM against hCA I, of 0.06-85.4 nM against hCA II; of 6.7-152 nM against hCA IX and of 0.49-237 nM against hCA XII; respectively. However no relevant isoform-selective behavior has been observed for any of them, although hCA II and XII, isoforms involved in glaucoma-genesis were the most inhibited ones. The structure-activity relationship for inhibiting the four CAs with these derivatives is discussed in detail.
- Bozdag, Murat,Alafeefy, Ahmed M.,Vullo, Daniela,Carta, Fabrizio,Dedeoglu, Nurcan,Al-Tamimi, Abdul-Malek S.,Al-Jaber, Nabila A.,Scozzafava, Andrea,Supuran, Claudiu T.
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p. 7751 - 7764
(2015/12/20)
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- Ruthenium(II) Catalyzed Regiospecific C-H/O-H Annulations of Directing Arenes via Weak Coordination
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Ruthenium(II) catalyzed oxidative C-H/O-H annulations have been demonstrated using two different directing arenes viz. 2-arylquinolinone and 2-arylbenzoxazinone with internal alkynes. Regiospecific annulations have been observed for both directing arenes via the assistance of weaker carbonyl oxygen in the presence of a stronger nitrogen-directing site. In this substrate-controlled convergent protocol the weaker directing group dictates the annulation path.
- Banerjee, Arghya,Santra, Sourav Kumar,Mohanta, Prakash Ranjan,Patel, Bhisma K.
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supporting information
p. 5678 - 5681
(2015/12/01)
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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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- 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
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supporting information
p. 2991 - 2993
(2014/05/06)
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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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- Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source
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Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.
- Li, Wanfang,Wu, Xiao-Feng
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p. 10410 - 10416
(2015/02/19)
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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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- 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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- 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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- 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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- 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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- 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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- Pd-carbene catalyzed carbonylation reactions of aryl iodides
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A series of carbene complexes [PdBr2(iPr 2-bimy)L] (C2-C13) with different types of co-ligands (L) have been tested for their catalytic activities in the carbonylative annulation of 2-iodophenol with phenylacetylene in DMF to afford the respective flavone 2a. Complex C12 with an N-phenylimidazole co-ligand showed the best activity and also afforded high yields when the substrate scope was extended to other aryl or pyridyl acetylenes. In addition, catalyst C12 was also efficient in the carbonylative annulation of 2-iodoaniline with acid chlorides giving the desirable 2-substituted 4H-3,1-benzoxazin-4-ones (4) in good yields. Additionally, this Pd-NHC complex also proved to be a very efficient catalyst for the hydroxycarbonylation of iodobenzene derivatives at low catalyst loading and under low CO pressure. These results demonstrate the versatility and efficiency of this phosphine-free Pd(ii)-NHC complex in different types of carbonylations of aryl iodides under mild conditions. The Royal Society of Chemistry 2011.
- Xue, Liqin,Shi, Lijun,Han, Yuan,Xia, Chungu,Huynh, Han Vinh,Li, Fuwei
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experimental part
p. 7632 - 7638
(2011/10/09)
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- Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives
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Two series of some new 2,4,6-trisubstituted-quinazoline derivatives were prepared and screened for their analgesic, anti-inflammatory activity and acute toxicity. Four compounds were more potent analgesic agents than the reference drug Indomethacin and thirteen compounds showed significant anti-inflammatory activity. Seven compounds showed combined ability to inhibit both pain and inflammation. Compounds tested for acute toxicity showed no toxic symptoms or mortality rates 24 h post-administration implying their good safety margin.
- Alafeefy, Ahmed M.,Kadi, Adnan A.,Al-Deeb, Omar A.,El-Tahir, Kamal E.H.,Al-Jaber, Nabila A.
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scheme or table
p. 4947 - 4952
(2010/11/20)
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- Synthesis and anti-inflammatory activity of 2,3-diaryl-4(3H)-quinazolinones
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2,3-Diaryl-4(3H)-quinazolinones containing various substituents on diaryl rings have been synthesized and evaluated for their cyclooxygenase-2 inhibitory activity by the colorimetric COX (ovine) inhibitor screening assay and anti-inflammatory activity by the carrageenan-induced rat paw edema assay. 2-(4-Nitrophenyl)-3-(4-tolyl)-4(3H)-quinazolinone showed a maximum COX-2 inhibition of 27.72% at 22 μM concentration in the present series and exhibited a mild anti-inflammatory activity at a dose of 50 mg/kg in carrageenan-induced rat paw edema assay.
- Yadav,Shirude,Parmar,Balaraman,Giridhar
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p. 1038 - 1045
(2008/09/16)
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- A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids
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A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.
- Khajavi, Mohammad S.,Shariat, Seyed M.
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p. 1159 - 1165
(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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- 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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