A facile and efficient synthesis of 4H-1,3-benzoxazine-4-one with electron-withdrawing group derivatives

Li, Peng; Zhang, Xinwei; Wu, Yongqi; Cheng, Maosheng; Zhang, Dongfeng; Li, Gang; Lin, Ziyun; Zhang, Xiang; Huang, Huanwei

doi:10.1016/j.tetlet.2015.06.034

Cited by 5 publications

(3 citation statements)

References 14 publications

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“…2-Chloro-3-nitro-5-(trifluoromethyl)benzamide (8) [11] was treated with oxalyl chloride followed by an appropriate amine to afford intermediates 9a-r. Compounds 9a-r were heated in DMF in the presence of K2CO3 to give benzoxazinones 5a-r after purification by column chromatography [20]. Benzothiopyranones 6a-r were prepared by a two-steps process.…”

Section: Chemistrymentioning

confidence: 99%

Identification of novel benzothiopyranone compounds against Mycobacterium tuberculosis through scaffold morphing from benzothiazinones

Wang

Zhang

Batt

et al. 2018

European Journal of Medicinal Chemistry

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In this study, three novel series of benzoxazinone, benzothiopyranone and benzopyranone derivatives were designed and synthesized through scaffold morphing from benzothiazinones targeting DprE1. All compounds were evaluated for their in vitro activities against Mycobacterium tuberculosis (M. tuberculosis) and cytotoxicity against Vero cell line. Among the three series, the benzothiopyranone series displayed excellent antimycobacterial activity and low cytotoxicity. Compound 6b exhibited potent in vitro activity against both drug-susceptible and drug-resistant M. tuberculosis clinical strains with MICs < 0.016 μg/mL. In addition, compound 6b demonstrated excellent ADME/T and PK properties and potent in vivo efficacy with bactericidal activity comparable to human equivalent dose of isoniazid (INH) in an acute mouse model of TB. Compound 6b which exhibits good inhibitory activity against DprE1 is under evaluation as a potential drug candidate for the treatment of tuberculosis. The current study provided new insight into the structural and pharmacological requirements for DprE1 inhibitors as potent antitubercular agents.

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Section: Chemistrymentioning

confidence: 99%

Identification of novel benzothiopyranone compounds against Mycobacterium tuberculosis through scaffold morphing from benzothiazinones

Wang

Zhang

Batt

et al. 2018

European Journal of Medicinal Chemistry

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“…Benzoxazines are of particular interest and have been reported to possess antimicrobial, anticancer, and antiplatelet activities. However, preparation of this valuable heterocycle is limited to a handful of synthetic routes which often require hazardous reagents, cumbersome preparation of starting materials and reagents or, alternatively, are restricted to electron‐withdrawing substituents in the benzene ring (Scheme a–e) . Palladium‐catalyzed carbonylation reactions such as aminocarbonylation and cross‐coupling reactions have become essential tools for synthesizing heterocycles and immense effort has been invested in developing safer methods for handling the toxic carbon monoxide gas .…”

Section: Introductionmentioning

confidence: 99%

“…However,p reparation of this valuableh eterocycle is limited to ah andful of synthetic routes which often require hazardous reagents, cumbersome preparation of starting materials and reagentso r, alternatively, are restricted to electron-withdrawing substituents in the benzene ring (Scheme 1a-e). [7][8][9][10][11][12] Palladium-catalyzed carbonylation reactions such as aminocarbonylation and cross-coupling reactions have become essentialt ools for synthesizingh eterocycles and immense effort has been invested in developing safer methods for handling the toxic carbon monoxide gas. [13][14][15] Over the last decade, several non-gaseous CO sourcesh ave been reported both for in situ and ex situ use, for example, formates, [16,17] formamides, [18] aldehydes, [19] formic acid [20] and metal carbonyls such as Mo(CO) 6 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4H‐Benzo[e][1,3]oxazin‐4‐ones by a Carbonylation–Cyclization Domino Reaction of ortho‐Halophenols and Cyanamide

et al. 2017

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A mild and convenient one‐step preparation of 4H‐1,3‐benzoxazin‐4‐ones by a domino carbonylation–cyclization process is developed. Readily available ortho‐iodophenols are subjected to palladium‐catalyzed carbonylative coupling with Mo(CO)6 and cyanamide, followed by a spontaneous, intramolecular cyclization to afford 4H‐1,3‐benzoxazin‐4‐ones in moderate to excellent yields. Furthermore, the scope of the reaction is extended to include challenging ortho‐bromophenols. Finally, to highlight the versatility of the developed method, Mo(CO)6 is successfully replaced with a wide array of CO‐releasing reagents, such as oxalyl chloride, phenyl formate, 9‐methylfluorene‐9‐carbonyl chloride, and formic acid, making this an appealing strategy for the synthesis of 4H‐benzo[e][1,3]oxazin‐4‐ones.

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ChemInform Abstract: A Facile and Efficient Synthesis of 4H‐1,3‐Benzoxazine‐4‐one with Electron‐Withdrawing Group Derivatives.

Zhang

Cheng

et al. 2015

ChemInform

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A Facile and Efficient Synthesis of 4H-1,3-Benzoxazine-4-one with Electron--Withdrawing Group Derivatives. -Electron-withdrawing substituents on the phenyl ring facilitate the base mediated heterocyclization of o-halobenzoylureas to afford benzoxazinones. -(LI, P.; ZHANG, X.; WU, Y.; CHENG, M.; ZHANG, D.; LI, G.; LIN, Z.; ZHANG, X.; HUANG*, H.; Tetrahedron Lett. 56 (2015) 32, 4683-4685, http://dx.

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A facile and efficient synthesis of 4H-1,3-benzoxazine-4-one with electron-withdrawing group derivatives

Cited by 5 publications

References 14 publications

Identification of novel benzothiopyranone compounds against Mycobacterium tuberculosis through scaffold morphing from benzothiazinones

Identification of novel benzothiopyranone compounds against Mycobacterium tuberculosis through scaffold morphing from benzothiazinones

Synthesis of 4H‐Benzo[e][1,3]oxazin‐4‐ones by a Carbonylation–Cyclization Domino Reaction of ortho‐Halophenols and Cyanamide

ChemInform Abstract: A Facile and Efficient Synthesis of 4H‐1,3‐Benzoxazine‐4‐one with Electron‐Withdrawing Group Derivatives.

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