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Mannich反应合成新型4-甲基-2-芳胺甲基苯酚类化合物 被引量：1

Synthesis of novel 2-arylaminomethyl-4-methyl phenols by Mannich reaction
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摘要 以对甲酚、多聚甲醛和取代苯胺为原料,利用Mannich反应法和"分步反应法"合成了一系列新型4-甲基-2-芳胺甲基苯酚,实验结果表明除苯环上没有取代基的产物(4a)外,其余产物经Mannich反应合成的产率均高于经"分步法"合成的产率.特别是经Mannich反应合成目标产物,减少了实验步骤、溶剂的使用和废物的排放,从而减少了环境污染,符合绿色化学的要求.用IR,1H NMR,13C NMR等对产物的结构进行了确证. A series of novel 2 - arylaminomethyl - 4 - methyl phenols were synthesized using p - cresol, paraformaldehyde and substituted anilines as materials by ＂fractional step methond＂ and Mannich reaction, respectively. The results showed the yields of the products prepared by Mannich reaction except for compound 4a without substituent on the benzen ring are higher than those obtained by ＂fractional step methond＂. In particular, the procedure through Mannich reaction is greatly simplified, and reduce the use of solvent and the release of the waste substance, and hence reduce the enviroment pollution. It is a green procedure for the preparation of this kind of products. The structures of the target compounds are characterized by IR, 1H NMR and 13 CNMR spectra.
作者 夏赞稳 颜林 唐子龙 唐瑞仁 李丽 黄勇 刘汉文
机构地区 湖南科技大学化学化工学院 理论化学与分子模拟省部共建教育部重点实验室 中南大学化学化工学院
出处 《湖南科技大学学报（自然科学版）》 CAS 北大核心 2012年第3期102-106,共5页 Journal of Hunan University of Science And Technology：Natural Science Edition
基金 国家自然科学基金(21042011) 湖南省教育厅重点项目(10A034) 湖南省博士后基金(2010RS4033) 理论化学教育部重点实验室开放基金课题(LKF0906)
关键词 分步法 MANNICH反应 4-甲基-2-芳胺甲基苯酚 合成 fractional step methond Mannich reaction 2 - arylaminomethyl - 4 - methyl phenol synthesis
分类号 O621 [理学—有机化学]
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参考文献15

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同被引文献21

  • 1Stokker G E, Deana A A, deSolms D S, et al. 2- (Aminomethyl) phenols, a new class of saluretie agents. Effects of nuclear substitution[J]. J Med Chem, 1980, 23:1 414-1 427.
  • 2Breckenridge R, Nicholson S, Nicol A, et al. Inhibition og neuronal gaba uptake and glial fl-alanine uptake by synthetic gaba analogues [J] . Biochem Pharmacol, 1981, 30:3 045-3 049.
  • 3Kragler A, Hofner G, Wanner K T. Synthesis and biological evaluation of aminomethylphenol derivatives as inhibitors of the murine GABA transporters mGATIemGAT4 [J ]. Eur J Med Chem, 2008, 43: 2404-2411.
  • 4Lee C H, Jin G F, Joung J G, ct al. New types of potential BNCT agents, o-carboranyl aminoalcohols [J ]. Tetrahedron Lett, 2009, 50: 2 960-2 963.
  • 5Lawrence R M, Dennis K C, Neill P M, et al. Development of a scalable synthetic route to GSK369796 (N-tert-Butyl Isoquine), a novel 4-aminoquinoline antimalarial drug[J ]. Org Proc Res Devel, 2008, 12: 294-297.
  • 6Cimarelli C, Palmieri G. Alkylation of dianions derived from 2- ( 1 -iminoalkyl)phenols : synthesis of functionalized 2 -acyl phenols[J].Tetrahedron, 1998, 54:15 711-15 720.
  • 7Waisser K, Gregor K, Kubicova L. et al. New groups of antimycobacterial agents : 6 -chloro -3 -pheny -4 -thioxo -2H - 1,3-benzoxazine-2 (3H)-ones and 6-Chloro-3-pheny|-4-2H- 1 , 3 -benzoxazine -2,4 ( 3H ) -dithiones [ J ]. Eur J Med Chem, 2000, 35: 733-741.
  • 8Waisser K, Gregor K, Dostal Ft, et al. Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-ary1-6,8-dichloro-2//-1,3- benzoxazine- ,4 (3H)-diones mad 3-Arylquinazoline-2,4 ( 1H, 3H)-diones[J].IlFarmaco, 2001, 56: 803-807.
  • 9Pasternak A, Goble S D, Struthers M, et al. Discovery of a potent and orally bioavailable CCR2 and CCR5 dual antagonist [J ]. ACS Med Chem Lett, 2010, 1 : 14-18.
  • 10TangZ, Chen W, Zhu H, et al. Synthesis of 2,3-diaryl-3,4- dihydro-2H-1,3-benzoxazines and their fungicidal activities [J ]. J Heterocyelic Chem, 2011, 48: 255-260.

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湖南科技大学学报（自然科学版）
2012年 第3期

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