N-烷基-1,2-苯并异噻唑啉-3-酮化合物的合成
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摘要
N-烷基-1,2-苯并异噻唑啉-3-酮类化合物具有优异的杀菌防腐性能,其不使用卤素的清洁合成方法尚未见文献报道。以二硫化二苯甲酸为起始原料,通过酰氯化、酰胺化制得两个N-烷基二硫化二苯酰胺,然后在强碱性溶液中将上述酰胺与双氧水进行氧化合环反应,得到两个N-烷基苯并异噻唑啉酮化合物。产物结构经红外和核磁表征。
N-Alkyl-1,2-benzisothiazdin-3-one is a kind of fungicides with efficient performance, but the green synthetic method of N-alkyl-1,2-benzisothiazdin-3-one without halogen has not been reported until now. Two N-alkyl-benzisothiazdin-3-ones were prepared from 2,2-dithiobis-benzoic acid by chloridization, acylation and oxidation with hydrogen peroxide in alkaline solution. The structure of products was identified by IR and ~1H NMR spectroscopy.
N-Alkyl-1,2-benzisothiazdin-3-one is a kind of fungicides with efficient performance, but the green synthetic method of N-alkyl-1,2-benzisothiazdin-3-one without halogen has not been reported until now. Two N-alkyl-benzisothiazdin-3-ones were prepared from 2,2-dithiobis-benzoic acid by chloridization, acylation and oxidation with hydrogen peroxide in alkaline solution. The structure of products was identified by IR and ~1H NMR spectroscopy.
引文
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[2] Yang J W,Zhang K Q,Li H,et al.Research Progress of Characterization and Synthesis of Benzisothiazolinone [J].Fine Spec Chem,2013,3:41-45 (in Chinese).(杨俊伟,张可青,李辉,等.苯并异噻唑啉酮类化合物的性质及合成进展[J].精细与专用化学品,2013,3:41-45.)
[3] Xu F L,Lin Q,Hou B R,et al.Synthesis and Bioactivity of Novel Benzisothiazolone Derivatives as Potential Microbiocides [J].J Heterocycl Chem,2009,46:320-323.
[4] Dou D F,Alex D,Du B F,et al.A Ntifungal Activity of a Series of 1,2-Benzisothiazol-3-one Derivatives [J].Bioorg Med Chem,2011,19:5 782-5 787.
[5] Li Y L,Li S L,Li Z Y,et al.Synthesis of N-Octyl-1,2-benisothiazolin-3-one [J].J South China Norm Univ (Nat Sci),1997,4:53 (in Chinese).(李育麟,李淑琏,李志勇.N-正辛基-1,2-苯并异噻唑啉-3-酮的合成研究[J].华南师范大学学报(自然科学版),1997,4:53.)
[6] Fang Y Q,Zhang Y.Synthesis of N-Methyl-benzisothiazolin-3-one [J].Chem World,2009,50(6):361 (in Chinese).(方永勤,张雁.N-甲基-1,2-苯并异噻唑啉-3-酮的合成研究[J].化学世界,2009,50(6):361.)
[7] Ni Y,Yan W C,Geng J Y,et al.Preparation of New Industrial Anti-mildew Bactericide:1,2-Benzisothiazdin-3-one [J].Fine Spec Chem,2004,12(20):21 (in Chinese).(倪越,严万春,耿金懿,等.新工业防霉杀菌剂1,2-苯并异噻唑啉-3-酮的研制[J].精细与专用化学品,2004,12(20):21.)
[8] Zhao S Y,Liu S C,Xu Y J,et al.The Synthesis and Platelet Aggregation Inhibitory Activities of 2,2-Dithiodibenzoic Acid Derivatives [J].Chin J Med Chem,1999,9(3):167 (in Chinese).(赵圣印,刘少诚,许佑军,等.2 ,2-二硫代双苯甲酸衍生物的合成及其抗血小板聚集作用[J].中国药物化学杂志,1999,9(3):167.)
[9] Fang Y Q,Zhang Y.Synthesis of N-Methyl-benzisothiazolin-3-one [J].Chem World,2009,50(6):361 (in Chinese).(方永勤,张雁.N-甲基-1,2-苯并异噻唑啉-3-酮的合成研究[J].化学世界,2009,50(6):361.)
[10] Zhang K Q,Ren R,Yang J W,et al.Synthesis of 1,2-Benzisothiazolin-3-one by Oxidation [J].Appl Chem Ind,2014,43(9):90-92 (in Chinese).(张可青,任蕊,杨俊伟,等.氧化法制备1,2-苯并异噻唑啉-3酮[J].应用化工,2014,43(9):90-92.)
[11] Tong G T,Weng J Q.Study on Synthesis of 1,2-Benzisothiazolin-3-one [J].Chem World,2013,4:231-240 (in Chinese).(童国通,翁建全.抑菌1,2-苯并异噻唑啉-3-酮 (BIT) 的合成研究[J].化学世界,2013,4:231-240.)
[12] Li H,Liu X Y,Wang W,et al.Theoretical Study on the Reaction of N-(4-Dehydrophenyl) Pyridiniumion with Nitroxides Within the Steric Effects [J].J Mol Sci,2012,28(3):192-196 (in Chinese).(李慧,刘翔宇,汪伟,等.位阻效应对N-(4-脱氢苯基)吡啶离子与氮氧自由基反应的理论计算研究[J].分子科学学报,2012,28(3):192-196.)
[13] Wang Y.Study on the Catalytic Oxidation Performance of Quinone [D].Zhengzhou:Zhengzhou University,2010 (in Chinese).(王瀛.醌类化合物催化氧化性能的研究[D].郑州:郑州大学,2010.)