Efficient One-Pot Synthesis of Substituted 4,7-Phenanthroline, Pyrano-[3,2-f]quinoline and Pyrano[3,2-g]quinoline Derivatives by Aza-Diels-Alder Reaction

被引:39
作者
Majumdar, K. C. [1 ]
Ponra, Sudipta [1 ]
Ghosh, Debankan [1 ]
Taher, Abu [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
关键词
multicomponent reaction; BF3 center dot OEt2; 4,7-phenanthroline; pyrano[3,2-f]quinoline; pyrano[3,2-g]quinoline; aromatic aldehyde; phenyl acetylene; FACILE SYNTHESIS; CONJUGATED POLYQUINOLINES; OPTICAL-PROPERTIES; PHASE SYNTHESIS; SOLID-PHASE; IN-VITRO; QUINOLINE; PYRANOQUINOLINE; PYRANO; DOMINO;
D O I
10.1055/s-0030-1259105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient method for the synthesis of pyrano[3,2-f] quinoline and 4,7-phenanthroline derivatives via three-component domino reaction of heterocyclic amines, aldehydes, and terminal alkyne using BF3 center dot OEt2 as Lewis acid catalyst is described. The features of this procedure are mild reaction conditions, good to high yields, and operational simplicity.
引用
收藏
页码:104 / 110
页数:7
相关论文
共 95 条
[71]   In vivo and in vitro production of alkaloids by Haplophyllum patavinum [J].
Puricelli, L ;
Innocenti, G ;
Delle Monache, G ;
Caniato, R ;
Filippini, R ;
Cappelletti, EM .
NATURAL PRODUCT LETTERS, 2002, 16 (02) :95-100
[72]   Quinoline alkaloids: Synthesis of pyrano[2,3-b]quinolines, khaplofoline, lunacrine, and demethoxylunacrine [J].
Sekar, M ;
Prasad, KJR .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (02) :294-296
[73]   An efficient one-pot synthesis of pyrano- and furoquinolines employing two reusable solid acids as heterogeneous catalysts [J].
Srinivas, KVNS ;
Das, B .
SYNLETT, 2004, (10) :1715-1718
[74]   POLYQUINOLINES [J].
STILLE, JK .
MACROMOLECULES, 1981, 14 (03) :870-880
[75]  
Takahashi K, 1986, Oyo Yakuri, V32, P233
[76]   Domino reactions in organic synthesis [J].
Tietze, LF .
CHEMICAL REVIEWS, 1996, 96 (01) :115-136
[77]   2,4,5-Trisubstituted thiazole building blocks by a novel multi-component reaction [J].
Umkehrer, M ;
Kolb, J ;
Burdack, C ;
Hiller, W .
SYNLETT, 2005, (01) :79-82
[78]   An efficient protocol for the liquid-phase synthesis of furanoquinolines and pyranoquinolines [J].
Wang, YG ;
Lin, XF ;
Cui, SJ .
SYNLETT, 2004, (07) :1175-1178
[79]   Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors [J].
Wang, Zhen ;
Zhou, Luyuan ;
El-Boubbou, Kheireddine ;
Ye, Xin-Span ;
Huang, Xuefei .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6409-6420
[80]   Discovery of new multi component reactions with combinatorial methods [J].
Weber, L ;
Illgen, K ;
Almstetter, M .
SYNLETT, 1999, (03) :366-374