邻氨基苯甲酰胺一锅法合成喹唑啉酮类化合物研究进展

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英文篇名：One-pot Synthesis of Quinazolinones with 2-Aminobenzamide 作者：许航线 英文作者：XU Hang-xian;Department of Chemical Engineering,Shaan Institute of Technology; 关键词：邻氨基苯甲酰胺 ; 一锅法 ; 合成 ; 喹唑啉酮 英文关键词：o-aminobenzamide;;one-pot;;synthesis;;quinazolinone 中文刊名：合成材料老化与应用 英文刊名：Synthetic Materials Aging and Application 机构：陕西国防工业职业技术学院化学工程学院; 出版日期：2019-08-15 出版单位：合成材料老化与应用 年：2019 期：04 语种：中文; 页：140-143 页数：4 CN：44-1402/TQ ISSN：1671-5381 分类号：O626

摘要

喹唑啉酮类化合物是一类具有良好生物活性的含氮杂环化合物,例如抗炎[1]、抗菌[2]、抗高血压[3]及抗癌[4]活性等,引起了科学研究人员的极大兴趣。该文对近些年以邻氨基苯甲酰胺为原料一锅法合成喹唑啉酮类化合物的方法进行了综述,并对未来的发展进行了展望。
        Quinazolinones are a class of nitrogen-containing heterocyclic compounds with good biological activity,such as anti-inflammatory,antibacterial,antihypertensive and anti-cancer abilities,and aroused great interest from scientific researchers. This artical reviews the methods on one-pot synthesis of quinazolinones with o-aminobenzamide,and the future development is looked forward too.

引文

[1]Halova-Lajoie B,Brumas V,Fiallo M M L,et al.Copper(II)interactions with non-steroidal antiinflammatory agents. 3-methoxyanthranilic acid as a potential OH-inactivating ligand:a quantitative invevestigation of its copper handling role in vivo[J]. J. Inorg. Biochem.,2006,100:362-373.
    [2] Pereira M de F,Chevrot R,Rosenfeld E,et al.Synthesis and evaluation of the antimicrobial activity of novel quinazolinones[J]. J. EnzInhib.Med. Chem.,2007,22:577-583.
    [3]Ram V J,Farhanullah,Tripathi B K,et al. Synthesis andantihyperglycemic activity of suitably functionalized 3H-quinazolin-4-ones[J]. Bioorg.Med. Chem.,2003,11(11):2439-2444.
    [4]Berman E M,Werbel L M. The renewed potential for folate antagonists in contemporary cancer chemotherapy[J]. J. Med. Chem.,1991,34(2):479-485.
    [5]许航线.喹唑啉酮及其衍生物的催化合成研究新进展[J].化学工程师,2016,10:48-53.
    [6]王伟立. SbCl3促进的喹唑啉酮衍生物和喹喔啉衍生物的合成[D].山东济南:山东轻工业学院,2012.
    [7]王树良,杨科,王香善.离子液体中Yb(OTf)3催化下喹唑啉酮衍生物的绿色合成[J].有机化学,2011,31(8):1235-1239.
    [8]FANG J,ZHOU J. One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers[J].J. Org. Chem.,2011,76(19):7730-7736.
    [9] Durgareddy G,Vikumar R,Ravi S,et al. A Cu(NO3)2·3H2O catalysed facile synthesis of substituted 4(3H)-quinazolinones and benzimidazoles[J]. J. Chem. Sci.,2013,125(1):175-182.
    [10]王敏,高晶晶,向刚伟,等. 2-取代-2,3-二氢-4(1H)-喹唑啉酮衍生物合成方法[J].石油化工高等学校学报,2011,24(3):13-16.
    [11] Gutiérrez-Bonetálvaro,Remeur Camille,Matsui Jennifer K,et al. Late-stage C-H alkylation of heterocycles and 1,4-quinones via oxidative homolysis of 1,4-dihydropyridines[J]. J. Am.Chem. Soc.,2017,139(35):12251-12258.
    [12]孙佳婧,周利凯,谭官海,等.喹唑啉-4-酮衍生物的合成及抗肿瘤活性[J].有机化学,2017,37:455-461.
    [13]罗文锋,姚舜,柳加兵,等.新型离子液体催化合成喹唑啉酮衍生物的研究[J].华西药学杂志,2012,27(1):061-063.
    [14]Rahimjzadeh M,Tavallai Z,Bakavoli M. Microwave irradiation in solvent-free conditions:Preparation of 2-substituted-4(3H)quinazolinones by heterocyclisation of 2-aminobenzamide with carboxylic acids[J]. Indian journal of Chemistry,2004,438:679-681.
    [15]Baker B R,Almaula P I. Nonclassical Antimetabolites. X. 1,2A Facile Synthesis of 4-Quinazolone-2-carboxylic Acidand the Structure of Bogert's AmmoniumSalt[J]. J. Org. Chem.,1962,27:4672-4674.
    [16]Hour M J,Huang L J,Kuo S C,et al. 6-Alkylamino-and 2,3-Dihydro-3'-methoxy-2-phenyl-4-quinazolinones and Related Compounds:Their Synthesis,Cytotoxicity,and Inhibition of Tubulin Polymerization[J]. J. Med. Chem.,2000,43(23):4479-4483.
    [17]Kim N Y,Cheon C H. Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO[J]. Tetrahedron. Lett.,2014,55(19):2340-2344.
    [18]Bashir A,Bhat D,Sahu P. One Pot Synthesis of4(3H)-Quinazolinones[J]. Synthetic. Commun.,2004,34(12):2169-2176.
    [19]Bakavoli M,Li Shiri A,Ebra Z,et al. Clean heterocyclic synthesis in water:I2/KI catalyzed onepot synthesis of quinazolin-4(3H)-ones[J].Chinese. Chem. Lett.,2008,19(12):1403-1406.