Synthesis of New Functionalized 1,4-Dihydroquinolines and Pyrimido[4,5-b]quinolines

被引:6
作者
Khoramdelan, F. [1 ]
Davoodnia, A. [1 ]
Bozorgmehr, M. R. [1 ]
Ebrahimi, M. [1 ]
机构
[1] Islamic Azad Univ, Mashhad Branch, Dept Chem, Mashhad 9175687119, Iran
关键词
dihydroquinoline; pyrimido[4,5-b]quinoline; POCl3; carboxylic acids; ONE-POT SYNTHESIS; MICROWAVE-ASSISTED SYNTHESIS; QUINOLINE DERIVATIVES; ANTIVIRAL ACTIVITY; ANTIOXIDANT; ULTRASOUND; GLYCOSIDES; FACILE;
D O I
10.1134/S1070363217120386
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of N-alkylisatoic anhydrides with malononitrile in pyridine led to formation of new 2-amino-1-alkyl-4-oxo-1,4-dihydroquinoline-3-carbonitriles. Following treatment of these compounds with an excess of aliphatic carboxylic acids in the presence of POCl3 under reflux gave novel 2,10-dialkylpyrimido[4,5-b]quinoline-4,5(3H,10H)-diones with high yields. It is probable that synthesis of the latter products proceed via the tandem intramolecular Pinner-Dimroth rearrangement. All synthesized compounds were characterized by spectral and microanalytical data.
引用
收藏
页码:2961 / 2965
页数:5
相关论文
共 29 条
[1]   Design, synthesis and biological evaluation of new 4-(4-substituted-anilino)quinoline derivatives as anticancer agents [J].
Abdellatif, Khaled R. A. ;
Abdelall, Eman K. A. ;
Abdelgawad, Mohamed A. ;
Amin, Dina M. E. ;
Omar, Hany A. .
MEDICINAL CHEMISTRY RESEARCH, 2017, 26 (05) :929-939
[2]   Synthesis of New Imino Containing Tetrahydrochromeno[2,3-d]pyrimidines [J].
Ameli, Shohreh ;
Davoodnia, Abolghasem ;
Pordel, Mehdi ;
Behmadi, Hossein .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (02) :1437-1441
[3]   Ultrasound- and microwave-assisted synthesis of (E)-1-aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1-ones and (E)-1-aryl-3-[2-(pyrrolidin-1-yl)quinolin-3-yl]prop-2-en-1-ones, and their antimicrobial activity [J].
Ashok, D. ;
Ganesh, Arram ;
Lakshmi, B. Vijaya ;
Ravi, S. .
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2014, 84 (06) :1237-1242
[4]   Antitumor activity of novel pyrrolo[2,3-d]pyrimidin-4-ones [J].
Atapour-Mashhad, Hoda ;
Tayarani-Najaran, Zahra ;
Davoodnia, Abolghasem ;
Moloudi, Raheleh ;
Mousavi, Seyed Hadi .
DRUG AND CHEMICAL TOXICOLOGY, 2011, 34 (03) :271-276
[5]   Copper-catalyzed tandem N-arylation/condensation: synthesis of quinazolin-4(3H)-ones from 2-halobenzonitriles and amides [J].
Chai, Hongxin ;
Li, Jiarong ;
Yang, Liupan ;
Lu, Hongyan ;
Qi, Zhang ;
Shi, Daxin .
RSC ADVANCES, 2014, 4 (84) :44811-44814
[6]   Synthesis, antifungal activity and CoMFA analysis of novel l,2,4-triazolo[1,5-a]pyrimidine derivatives [J].
Chen, Qiong ;
Zhu, Xiao-Lei ;
Jiang, Li-Li ;
Liu, Zu-Ming ;
Yang, Guang-Fu .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :595-603
[7]   1,3-Dipolar Cycloaddition-Decarboxylation Reactions of an Azomethine Ylide with Isatoic Anhydrides: Formation of Novel Benzodiazepinones [J].
D'Souza, Asha M. ;
Spiccia, Nadia ;
Basutto, Jose ;
Jokisz, Pawel ;
Wong, Leon S. -M. ;
Meyer, Adam G. ;
Holmes, Andrew B. ;
White, Jonathan M. ;
Ryan, John H. .
ORGANIC LETTERS, 2011, 13 (03) :486-489
[8]   Microwave-assisted synthesis of new pyrimido[4′,5′:4,5]thiazolo[3,2-a] benzimidazol-4(3H)-one derivatives in solvent-free condition [J].
Davoodnia, A. ;
Roshani, M. ;
Saleh-Nadim, E. ;
Bakavoli, M. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2007, 18 (11) :1327-1330
[9]   A facile one-pot synthesis of new thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione derivatives [J].
Davoodnia, A. ;
Behmadi, H. ;
Zare-Bidaki, A. ;
Bakavoli, M. ;
Tavakoli-Hoseini, N. .
CHINESE CHEMICAL LETTERS, 2007, 18 (10) :1163-1165
[10]   Synthesis of pyrido[3′,2′:4,5]thieno[2,3-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-one derivatives [J].
Davoodnia, Abolghasem ;
Bakavoli, Mehdi ;
Mohseni, Sharare ;
Tavakoli-Hoseini, Niloofar .
MONATSHEFTE FUR CHEMIE, 2008, 139 (08) :963-965