溴化金催化醛及芳香胺串联反应合成2,3-二取代喹啉
AuBr_3-catalyzed tandem reaction of aldehydes and arylamines to synthesize 2,3-disubstituted quinolines
作者:马俊雨;郭娜;成明;杜锋田;姬建新;张强;
Author:
收稿日期: 年卷(期)页码:2015,30(05):-525-527
期刊名称:华西药学杂志
Journal Name:WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字:溴化金;催化;串联反应;醛;芳香胺;合成;喹啉
Key words:
基金项目:国家自然科学基金资助项目(批准号:21172213,2140020768)
中文摘要
目的建立简单、快捷合成喹啉类化合物的方法。方法以溴化金为催化剂,THF为溶剂,在60℃下,催化芳香胺和脂肪醛合成喹啉类化合物。结果和讨论合成了一系列2,3-二取代喹啉类化合物,结构经1HNMR、13CNMR和HR-MS表征。该反应具有操作简便、原料易得、条件温和、时间短等优点。
英文摘要
[1]Micheal JP.Quinoline,quinazoline and acridone alkaloids[J].Nat Prod Rep,1999,16(6):697-709.
[2]Kumar S,Bawa S,Gupta S.Biological activities of quinolone derivatives[J].Mini-Rev Med Chem,2009,9(14):1648-1654.
[3]Manske RHF.The chemistry of quinolines[J].Chem Rev,1942,30(2):113-114.
[4]Marco-Contelles J,Pérez-Mayoral E,Samadi A,et al.Recent advances in the Friedlnder reaction[J].Chem Rev,2009,109(6):2652-2671.
[5]Denmark SE,Venkatraman S.On the mechanism of the SkraupDoebner-Von Miller quinoline synthesis[J].J Org Chem,2006,71(4):1668-1676.
[6]Arcadi A.Alternative synthetic methods through new developments in catalysis by gold[J].Chem Rev,2008,108(8):3267-3289.
[7]Waldmann H,Karunaker GV,Kumar K.Gold(Ⅲ)-mediated aldol condensations provide efficient access to nitrogen heterocycles[J].Org Lett,2008,10(11):2159-2162.
[8]Arcadi A,Chiarini M,Giuseppe SD,et al.A new green approach to the Friedlnder synthesis of quinolines[J].Synlett,2003,1(2):203-206.
[9]So MH,Liu YG,Ho CM,et al.Silica-supported gold nanoparticles catalyzed one-pot tandem aerobic oxidative cyclization reaction for nitrogen-containing polyheterocyclic compounds[J].Chem Cat Chem,2011,3(3):386-393.
[10]Zhang Q,Cheng M,Hu XY,et al.Gold-catalyzed three-component tandem process:An efficient and facile assembly of complex butenolides from alkynes,amines,and glyoxylic acid[J].J Am Chem Soc,2010,132(21):7256-7257.
[11]Cheng M,Zhang Q,Hu XY,et al.Gold-catalyzed direct intermolecular coupling of ketones,secondary amines,and alkynes:A facile and versatile access to propargylic amines containing a quaternary carbon center[J].Adv Synth Catal,2011,353(8):1274-1278.
[12]Nakajama T,Inada T,Igarashi T,et al.Facile three-component synthesis of substituted quinolines catalyzed by Iridium(Ⅲ)complex[J].Bull Chem Soc Jpn,2006,79(12):1941-1949.
【关闭】