An efficient one-pot synthesis of polyhydroquinoline derivatives through the Hantzsch four component condensation

被引:190
作者
Donelson, James L.
Gibbs, Richard A.
De, Surya K. [1 ]
机构
[1] Purdue Univ, Sch Pharm, Dept Med Chem & Mol Pharmacol, W Lafayette, IN 47907 USA
[2] Purdue Univ, Purdue Canc Ctr, W Lafayette, IN 47907 USA
关键词
polyhydroquinoline; Hantzsch reaction; scandium triflate;
D O I
10.1016/j.molcata.2006.03.079
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 [物理化学]; 081704 [应用化学];
摘要
A straightforward and general method has been developed for the synthesis of polyhydroquinolines derivatives by simply combining aldehyde, ethyl acetoacetate, dimedone, and ammonium acetate in the presence of a catalytic amount of scandium triflate. This method is very easy, rapid, and high yielding reaction for the synthesis of polyhydroquinolines. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:309 / 311
页数:3
相关论文
共 24 条
[1]
4-ARYLDIHYDROPYRIDINES, A NEW CLASS OF HIGHLY-ACTIVE CALCIUM-ANTAGONISTS [J].
BOSSERT, F ;
MEYER, H ;
WEHINGER, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (09) :762-769
[2]
Solid-phase synthesis of 4-aryl-1,4-dihydropyridines via the Hantzsch three component condensation [J].
Breitenbucher, JG ;
Figliozzi, G .
TETRAHEDRON LETTERS, 2000, 41 (22) :4311-4315
[3]
Scandium(III) triflate as an efficient and reusable catalyst for synthesis of 1,5-benzodiazepine derivatives [J].
De, SK ;
Gibbs, RA .
TETRAHEDRON LETTERS, 2005, 46 (11) :1811-1813
[4]
A mild and efficient one-step synthesis of quinolines [J].
De, SK ;
Gibbs, RA .
TETRAHEDRON LETTERS, 2005, 46 (10) :1647-1649
[5]
Bismuth trichloride catalyzed synthesis of α-aminonitriles [J].
De, SK ;
Gibbs, RA .
TETRAHEDRON LETTERS, 2004, 45 (40) :7407-+
[6]
Yttrium triflate as an efficient and useful catalyst for chemoselective protection of carbonyl compounds [J].
De, SK .
TETRAHEDRON LETTERS, 2004, 45 (11) :2339-2341
[7]
Ruthenium(III) chloride-catalyzed chemoselective synthesis of acetals from aldehydes [J].
De, SYK ;
Gibbs, RA .
TETRAHEDRON LETTERS, 2004, 45 (44) :8141-8144
[8]
Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides:: preparation via a polymer-assisted solution-phase approach [J].
Dondoni, A ;
Massi, A ;
Minghini, E ;
Bertolasi, V .
TETRAHEDRON, 2004, 60 (10) :2311-2326
[9]
GODFRAID T, 1986, PHARMACOL REV, V27, P321
[10]
Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines [J].
Gordeev, MF ;
Patel, DV ;
Gordon, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :924-928