Synthesis of New Dihydropyrimido[4,5-b]quinolinetrione Derivatives Using a Four-Component Coupling Reaction

被引:37
作者
Khalafi-Nezhad, A. [1 ]
Panahi, F. [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
来源
SYNTHESIS-STUTTGART | 2011年 / 06期
关键词
multicomponent reaction; pyrimidine; dihydropyridine; barbituric acid; dimedone; DIVERSITY-ORIENTED SYNTHESIS;
D O I
10.1055/s-0030-1258446
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient and one-pot method for the efficient synthesis of the novel 8,9-dihydro-8,8-dimethyl-5,10-diphenylpyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H,7H,10H)-trione derivatives via a four-component condensation reaction of aldehydes, amines, dimedone, and barbituric acid in the presence of tungestophosphoric acid (H3PW12O40) as catalyst is described. This new approach proceeded smoothly in good to excellent yields and the pure products are separated from the reaction mixture by simple filtration.
引用
收藏
页码:984 / 992
页数:9
相关论文
共 28 条
[1]   Selective cleavage of isopropyl aryl ethers by aluminium trichloride (vol 63, pg 9139, 1998) [J].
Banwell, MG ;
Flynn, BL ;
Stewart, SG .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6118-6118
[2]   Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones [J].
Bonne, Damien ;
Dekhane, Mouloud ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2485-2488
[3]   5-SUBSTITUTED PYRIMIDINE NUCLEOSIDES AND NUCLEOTIDES [J].
BRADSHAW, TK ;
HUTCHINSON, DW .
CHEMICAL SOCIETY REVIEWS, 1977, 6 (01) :43-62
[4]  
Brown J.D., 1984, COMPREHENSIVE HETERO, V3, P57
[5]   THE BIOCHEMISTRY AND MOLECULAR-BIOLOGY OF THE DIHYDROPYRIDINE-SENSITIVE CALCIUM-CHANNEL [J].
CAMPBELL, KP ;
LEUNG, AT ;
SHARP, AH .
TRENDS IN NEUROSCIENCES, 1988, 11 (10) :425-430
[6]   HIV-1-SPECIFIC RT INHIBITORS - HIGHLY SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 THAT ARE SPECIFICALLY TARGETED AT THE VIRAL REVERSE-TRANSCRIPTASE [J].
DECLERCQ, E .
MEDICINAL RESEARCH REVIEWS, 1993, 13 (03) :229-258
[7]   Electrochemically induced chain transformation of salicylaldehydes and alkyl cyanoacetates into substituted 4H-chromenes [J].
Elinson, Michail N. ;
Dorofeev, Alexander S. ;
Feducovich, Sergey K. ;
Gorbunov, Sergey V. ;
Nasybullin, Ruslan F. ;
Stepanov, Nikita O. ;
Nikishin, Gennady I. .
TETRAHEDRON LETTERS, 2006, 47 (43) :7629-7633
[8]   Heteropoly acids, their salts and polyoxometalates as heterogenous, efficient and eco-friendly catalysts in organic reactions: Some recent advances [J].
Firouzabadi, H. ;
Jafari, A. A. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2005, 2 (02) :85-114
[9]   Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction [J].
Ghahremanzadeh, Ramin ;
Fereshtehnejad, Fatemeh ;
Bazgir, Ayoob .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (04) :516-520
[10]  
GULLIYA KS, 1997, Patent No. 943385