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水相中微波辐射下铜催化合成苯并噻唑衍生物 被引量:1

Copper-catalyzed Microwave-assisted Synthesis of Benzothiazoles Derivatives in Water
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摘要 目的用微波辐射催化法在水相中合成苯并噻唑化合物。方法在150 W微波辐射条件下,以CuCl2和菲啰啉为催化剂,2-碘芳烃、芳醛和硫化钠在100℃水相中反应30min得到目标苯并噻唑化合物。结果合成得到9个相应的苯并噻唑化合物,均通过1 H NMR、13 C NMR和质谱确认结构,最高收率为94%。结论使用微波辐射法水相中合成目标产物,与传统方法相比,避免使用大量有机溶剂对环境造成污染,且具有时间短、收率高的优点。 Objective Benzothiazoles were synthesized under microwave irradiation in water . Methods A variety of 2-iodoanilines and aldehydes could be reacted with sodium sulfide to give the desired corresponding products in high yields in 100 ℃ water for 30 min using copper catalysts under microwave ir-radiation . Results We have developed an efficient protocol for benzothiazoles ,9 target compounds can be synthesized in good to excellent yields up to 94% , and all of them were further characterized by 1 H NMR ,13C NMR and MS analysis . Conclusion Synthesis of target benzothiazoles compounds under microwave irradiation in water has an advantage of short reaction time and higher the yields compared to the conventional method .
出处 《福建医科大学学报》 2013年第5期301-304,共4页 Journal of Fujian Medical University
基金 福建医科大学博士启动基金(2011BS006)
关键词 微波辅助合成 苯并噻唑 2-碘芳胺 芳醛 硫化钠 microwave-assisted synthesis Benzothiazoles 2-Iodoanilines Aldehydes Sodium sulfide
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参考文献6

  • 1Hofmann A W. Ueber die Einwirkung des Phosphorpentachlo- rids auf Senfo1e und verwandte K6rper[J]. Ber Dtsch Chem Ges, 1879, 12:1126 -1130.
  • 2Joycharat N, Greger H, Hofer O, et al. Flavaglines and triter- penoids from the leaves of aglaia forbesii[J]. Phytochemistry, 2008, 69:206- 211.
  • 3Soni B, Ranawat M S, Sharma R, etal. Synthesis and evalua- tion of some new benzothiazole derivatives as potential antimi- crobial agents [J]. Eur J Med Chem, 2010, 45 (7): 2938-2942.
  • 4Song J H, Huang C S, Nagata K, et al. Differential action of riluzole on tetrodotoxin-sensitive and tetrodotoxin-resistant so- dium channels[J]. J Pharmacol Exp Ther, 1997,282 (2) : 707-714.
  • 5Bahrami K, Khodaei M M, Naali F. H2Oz/Fe(NO3)3promo-ted synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J]. Synlett, 2009, 4:569-572.
  • 6游诚舨,游诚航,王向辉,李华燕,尹学琼,杨建新,林强.微波法合成2-羟乙基苯并[d]异噻唑-3(2H)-酮[J].化学研究与应用,2012,24(5):778-782. 被引量:6

二级参考文献13

  • 1P Borgna, MI Carmellino, M Natangelo, et al. Antiimicrobial activity of N-hydroxyalkyl 1,2-benzisothiazol-3 ( 2H )ones and their thiono analogues [ J ]. Eur J Med Chem , 1996,11 ( 31 ) :919-925.
  • 2Paola Vicini, Matteo Incerti, Paolo La Colla, et al. AntiHIV evaluation of benzo [d] isothiazole hydrazones [J]. Eur J Med ,2009,4(44) : 1801-1807.
  • 3Paola Vicini, Loredana Amoretti ,Vigilio ballabeni, et al. 2- Amino-benzol d ] isothiazol-3-one derivatives : synthesis and assessment of their antiplatelet/spasmolytic effects [ J ]. B/o Med Chem, 2000,9 ( 8 ) :2355-2358.
  • 4Yukihiro Ohno, Kumiko Ishida, Kazuhito Ikeda, et al. Evaluation of bradykinesia induction by SM-9018, a novel 5-HT2 and D2 receptor antagonist, using the mouse pole test [ J ]. Pharmolology Biochemistry and Behavior, 1994, 1 (49) :19-23.
  • 5Giuseppe Pagani, Pietro Borgna, Claudio Piersimoni, et al. In vitro anti-mycobacterium avium activity of N-( 2- hydroxyethyl )-1,2-benzisothiazol-3 ( 2H )-one and-thioneearbamic esters[ J]. Arch Pharm Pharm Med Chem, 1996, 8(329) :421-425.
  • 6Redye Gedye, Frank Smith, Kenneth Westaway, et al. The use of microwave ovens for rapid organic synthesis [ J ]. tetrahedron Lett, 1986,27 ( 3 ) :279-282.
  • 7Ajay K. Bose,Maghar S. Manhas, Malay Ghosh,et al. Microwave-induced organic reaction enhancement chemistry: 2. Simplified techniques [ J ]. J Org Chem, 1991,56 ( 25 ) : 6968-6970.
  • 8Santhosh Sivaramakrishnan, Andrea H Cummings, Kent S Gates. Protection of a single-cysteine redox switch from oxidative destruction: on the functional role of sulfenyl amide formation in the redox-regulated enzyme PTPI B [J]. Bio Med Chem,2010,2(20):444-447.
  • 9Jeno Varga, Denes Szabo, Cecilia P. Sar. et al. Stereospecific synthesis and hydrolysis of optically active diaryl (acylamino) (acyloxy) spiro-X4-sulfanes and related cyclic diaryl(acylamino) sulfonium salts [ J ]. Tetrahedron: Asymmetry ,2001,12( 5 ) ,745-753.
  • 10贺永宁,袁文,王向辉,杨建新,林强.2-(N-苯基甲酰胺基)苯并异噻唑啉-3-酮类化合物的合成及生物活性测试[J].海南大学学报(自然科学版),2007,25(4):345-348. 被引量:7

共引文献5

同被引文献11

  • 1Hofmann A W.Ueber die Einwirkung des Phosphorpentachlorids auf Senfle und Verwandte Krper[J].Ber Dtsch Chem Ges,1879,12(1):1126-1130.
  • 2Joycharat N,Greger H,Hofer O,et al.Flavaglines and Triterpenoids from the Leaves of Aglaia Forbesii [J].Phytochemistry,2008,69:206-211.
  • 3Soni B,Ranawat M S,Sharma R,et al.Synthesis and Evaluation of Some New Benzothiazole Derivatives As Potential Antimicrobial Agents[J].Eur J Med Chem,2010,45:2935-2942.
  • 4Song J H,Huang C S,Nagata K,et al.Differential Action of Riluzole on Tetrodotoxin-sensitive and Tetrodotoxin-resistant Sodium Channels[J].J Pharma-ol Exp Ther,1997,282(2):707-714.
  • 5Bahrami K,Khodaei M M,Naali F.H2 O2/Fe(NO3)3 Promoted Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles [J].Synlett,2009,4:569-572.
  • 6Chanda A.Fokin V V.Orzanic Synthesis "On Water" [J].Chem Rev.2009.109(2):725-748.
  • 7Gonzalez-Arellano C,Luque R,Macquarrie D J,et al.Microwave Efficient S-Arylation of Thiols with Aryl Iodides Using Supported Metal Nanoparticles[J].Chem Commun,2009,23:1410-1412.
  • 8Ma D,Xie S,Xue P,et al.Efficient and Economical Access to Substituted Benzothiazoles:Copper-Catalyzed Coupling of 2-Haloanilides with Metal Sulfides and Subsequent Condensation[J].Angew Chem Int Ed,2009,48(23):4222-4225.
  • 9Deng H,Li Z,Ke F,et al.Cu-Catalyzed Three-Component Synthesis of Substituted Benzothiazoles in Water[J].Chem Eur J,2012,18:4840-4843.
  • 10游诚舨,游诚航,王向辉,李华燕,尹学琼,杨建新,林强.微波法合成2-羟乙基苯并[d]异噻唑-3(2H)-酮[J].化学研究与应用,2012,24(5):778-782. 被引量:6

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