Synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolines via a one-pot, three-component reaction

被引:9
作者
Maleki, Ali [1 ]
Rezayan, Ali Hossein [2 ]
机构
[1] Iran Univ Sci & Technol, Dept Chem, Tehran 1684613114, Iran
[2] Univ Tehran, Fac New Sci & Technol, Dept Life Sci Engn, Tehran 143951561, Iran
基金
美国国家科学基金会;
关键词
Pyrido[2',1':2,3]imidazo[4,5-c]isoquinoline; Multicomponent reaction; Trimethylsilyl cyanide; Aminopyridine; Phthalaldehyde; MULTICOMPONENT REACTIONS; BINDING-SITE; DERIVATIVES; NANOPARTICLES; INHIBITORS; CHEMISTRY; RECEPTOR; ANALOGS; ACID;
D O I
10.1016/j.tetlet.2014.01.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot, three-component reaction for the synthesis of pyrido[2',1':2,3]imidazo[4,5-c]isoquinolines starting from 2-aminopyridines, phthalaldehyde, and trimethylsilyl cyanide in good to high yields is described. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1848 / 1850
页数:3
相关论文
共 29 条
[1]   A novel class of orally active non-peptide bradykinin B2 receptor antagonists.: 1.: Construction of the basic framework [J].
Abe, Y ;
Kayakiri, H ;
Satoh, S ;
Inoue, T ;
Sawada, Y ;
Imai, K ;
Inamura, N ;
Asano, M ;
Hatori, C ;
Katayama, A ;
Oku, T ;
Tanaka, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (04) :564-578
[2]   One-pot synthesis of quinoline-based tetracycles by a tandem three-component reaction [J].
Che, Chao ;
Xiang, Jing ;
Wang, Guo-Xin ;
Fathi, Reza ;
Quan, Jun-Min ;
Yang, Zhen .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (06) :982-989
[3]   Studies on the synthesis of benzimidazo [2,1-a] isoquinolines [J].
Deady, LW ;
Loria, PM ;
Rodemann, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (10) :941-945
[4]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[5]   Chemistry and Biology Of Multicomponent Reactions [J].
Domling, Alexander ;
Wang, Wei ;
Wang, Kan .
CHEMICAL REVIEWS, 2012, 112 (06) :3083-3135
[6]   Straightforward Bienayme and copper catalyzed N-arylation sequence to access diverse 5H-pyrido[2′,1′:2,3]imidazo[4,5-b]indoles and analogues [J].
El Akkaoui, Ahmed ;
Hiebel, Marie-Aude ;
Mouaddib, Abderrahim ;
Berteina-Raboin, Sabine ;
Guillaumet, Gerald .
TETRAHEDRON, 2012, 68 (44) :9131-9138
[7]   Imidazo[1,2-a]pyrimidines as functionally selective and orally bioavailable GABA-α2/α3 binding site agonists for the treatment of anxiety disorders [J].
Goodacre, SC ;
Street, LJ ;
Hallett, DJ ;
Crawforth, JM ;
Kelly, S ;
Owens, AP ;
Blackaby, WP ;
Lewis, RT ;
Stanley, J ;
Smith, AJ ;
Ferris, P ;
Sohal, B ;
Cook, SM ;
Pike, A ;
Brown, N ;
Wafford, KA ;
Marshall, G ;
Castro, JL ;
Atack, JR .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (01) :35-38
[8]   A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity [J].
Guchhait, Sankar Kumar ;
Chaudhary, Vikas ;
Madaan, Chetna .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) :9271-9277
[9]   Structure-based design of a new class of highly selective aminoimidazo[1,2-a]pyridine-based inhibitors of cyclin dependent kinases [J].
Hamdouchi, C ;
Zhong, B ;
Mendoza, J ;
Collins, E ;
Jaramillo, C ;
De Diego, JE ;
Robertson, D ;
Spencer, CD ;
Anderson, BD ;
Watkins, SA ;
Zhang, FM ;
Brooks, HB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (07) :1943-1947
[10]   Structural Requirements for Eszopiclone and Zolpidem Binding to the γ-Aminobutyric Acid Type-A (GABAA) Receptor Are Different [J].
Hanson, Susan M. ;
Morlock, Elaine V. ;
Satyshur, Kenneth A. ;
Czajkowski, Cynthia .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (22) :7243-7252