期刊文献+

Aza-Diels-Alder反应合成四氢喹啉的研究进展

Research Progress on Synthesis of Tetrahydroquinolines by Aza-Diels-Alder Reaction
下载PDF
导出
摘要 四氢喹啉类化合物具有广泛的生物活性,并且也是一类重要的染料中间体。综述了近几年由N-芳基亚胺与亲双烯体经aza-Diels-Alder反应合成四氢喹啉的反应,以及由羰基化合物、胺和烯醇醚"一锅法"合成四氢喹啉的进展。分析比较了路易斯酸催化、阳离子自由基催化、其他酸催化合成等不同合成方法的优缺点。由羰基化合物、胺和烯醇醚"一锅法"构建四氢喹啉骨架更加简便,具有广阔的发展前景。 Tetrahydroquinoline derivatives have a wide range of biological activities,and are also a kind of important dye intermediates. The reactions for the synthesis of tetrahydroquinoline derivatives by aza-Diels-Alder reactions between N- arylimines and dienophiles were reviewed. New developments in the "one- pot " synthesis of tetrahydroquinoline derivatives from the carbonyl compounds,amines,and enol ethers were also reviewed. Different synthetic methods,including Lewis acid catalysis,cation radical catalysis,and other acid catalysis were compared and discussed. Forming tetrahydroquinoline skeletons by "one-pot"synthesis from the carbonyl compounds,amines,and enol ethers is easier,and has broad prospects for development.
出处 《广州化工》 CAS 2015年第21期5-9,共5页 GuangZhou Chemical Industry
基金 国家自然科学基金(51302114) 江苏省自然科学基金(BK20131010)
关键词 四氢喹啉 aza-Diels-Alder反应 环加成反应 tetrahydroquinolines aza-Diels-Alder reaction cycloaddition
  • 相关文献

参考文献17

  • 1Babu G, Perumal P T. Convenient synthesis of pyrano [ 3,2 - c quinolines and indeno [ 2, 1 - c ] quinolines by imino Diels - Alder reactions[ J]. Tetrahedron Letters, 1998,39:3225-3228. 被引量:1
  • 2Crousse B, B6gu6 J, Bonnet - Delpon D. Synthesis of 2 - CF3 - tetrahydroquinoline and quinoline derivatives from CF3 -N- aryl- aldimine[ J]. The Journal of Organic Chemistry ,2000,65:5009-5013. 被引量:1
  • 3Sundararajan G, Prabagaran N, Varghese B. First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Aider reaction using chiral Ti (IV) complex [ J ]. Organic Letters, 2001,3 :1973-1976. 被引量:1
  • 4Lin X, Cui S, Wang Y. A highly efficient synthesis of 1,2,3,4- tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers [ J ]. Tetrahedron Letters, 2006,47 : 4509-4512. 被引量:1
  • 5Cheng D, Zhou J, Saiah E, et al. Ketene dithioacetals in the aza-Diels- Alder reaction with N - arylimines: a versatile approach to tetrahydroquinolines, 2,3 - dihydro- 4 - quinolones, and 4 - quinolones [ J]. Organic Letters,2002,4:4411-4414. 被引量:1
  • 6Stevenson P J, Nieuwenhuyzen M, Osborne D. Three eomponent coupling reactions of N-aectyl-2-azetine- rapid stcreoselective entry to 2,3,4-trisubstituted tetrahydroquinolines [ J ]. Chemical Communieations, 2002, 444-445. 被引量:1
  • 7Jia X, Lin H, Hun C, et al. Cation Radical Imino Diels- AlderReaetion : A new approach for the synthesis of tetrahydroquinolines [ J ]. Synlett, 2003 ( 11 ) : 1707-1709. 被引量:1
  • 8Zhang W, Jia X, Yang L, et al. Photosensitized Diels-Alder reactions of N-arylimines: synthesis of tetrahydroquinnline derivatives [J]. Tetrahedron Letters ,2002,43:9433-9436. 被引量:1
  • 9Zhang W, Gun Y, Liu Z, et al. Photochemically catalyzed Diels-Alder reaction of arylimines with N-vinylpyrrolidinone and N-vinylcarbazole by 2, 4, 6 - triphenylpyrylium salt: synthesis of 4 - heterocycle - substituted tetrahydroquinoline derivatives[J]. Tetrahedron,2005,61 : 1325-1333. 被引量:1
  • 10Nagarajan R, Chitra S, Perumal P T. Triphenyl phosphonium perchlorate-an efficient catalyst for the imino Diels-Alder reaction of imines with electron rich dienophiles. Synthesis of pyranoquinoline,furoquinoline and phenanthridine derivatives [ J ]. Tetrahedron, 2001, 57 : 3419-3423. 被引量:1

相关作者

内容加载中请稍等...

相关机构

内容加载中请稍等...

相关主题

内容加载中请稍等...

浏览历史

内容加载中请稍等...
;
使用帮助 返回顶部