Synthesis, Characterization, and Antimicrobial Evaluation of Some Novel 4-Hydroxyquinolin-2(1H)-ones

被引:19
作者
Ibrahim, Magdy A. [1 ]
Hassanin, Hany M. [1 ]
Alnamer, Youssef A. [1 ]
机构
[1] Ain Shams Univ, Fac Educ, Dept Chem, Cairo 11711, Egypt
关键词
RORC; Cyclocondensation; pyrano[3,2-c]quinolinone; Vilsmeier-Haack reaction; 4-hydroxyquinolin-2(1H)-one; CHEMICAL BEHAVIOR; NUCLEOPHILIC-REAGENTS; SERIES; ACID; DERIVATIVES;
D O I
10.1080/00397911.2014.949775
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vilsmeier-Haack formylation of 3-acetyl-1-methyl-4-hydroxyquinolin-2(1H)-one (2) produced the novel 6-methyl-4,5-dioxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxaldehyde (3). Reactions of carboxaldehyde 3 with a diversity of nucleophilic reagents were studied and a variety of products were obtained via ring-opening, ring-closing (RORC) sequence. Also, some novel heteroannulated pyrano[3,2-c]quinolines were prepared. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.
引用
收藏
页码:3470 / 3482
页数:13
相关论文
共 23 条
[1]   Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX [J].
Abass, M ;
Mostafa, BB .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (22) :6133-6144
[2]   Substituted quinolinones. Part 17: Some nucleophilic reactions with 4-hydroxy-1-methyl-3-[(2-oxo-2H-chromen-3-yl)carbonyl]quinolin-2(1H)-one [J].
Abass, Mohamed ;
Mohamed, El-Hussain A. ;
Mayas, Aisha S. ;
Ibrahim, Akram H. .
JOURNAL OF CHEMICAL SCIENCES, 2012, 124 (05) :1033-1041
[3]   4-cyano-6,7-dimethoxycarbostyrils with solvent- and pH-independent high fluorescence quantum yields and emission maxima [J].
Ahvale, Appasaheb B. ;
Prokopcova, Hana ;
Sefcovicova, Jana ;
Steinschifter, Waltraud ;
Taeubl, Anna E. ;
Uray, Georg ;
Stadlbauer, Wolfgang .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) :563-571
[4]   Synthesis, Characterization and Biological Activities of Cu(II), Co(II), Mn(II), Fe(II), and UO2(VI) Complexes with a New Schiff Base Hydrazone: O-Hydroxyacetophenone-7-chloro-4-quinoline Hydrazone [J].
Al-Shaalan, Nora H. .
MOLECULES, 2011, 16 (10) :8629-8645
[5]   New polycyclic pyrimidine derivatives with antiplatelet in vitro activity: Synthesis and pharmacological screening [J].
Bruno, O ;
Schenone, S ;
Ranise, A ;
Bondavalli, F ;
Barocelli, E ;
Ballabeni, V ;
Chiavarini, M ;
Bertoni, S ;
Tognolini, M ;
Impicciatore, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :629-636
[6]   Multivariate SAR/QSAR of 3-aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase (FAS) inhibitors [J].
de Melo, Eduardo Borges .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) :5817-5826
[7]   Selective 15N-Labeling and Analysis of 13C-15N J Couplings as an Effective Tool for Studying the Structure and Azide-Tetrazole Equilibrium in a Series of Tetrazolo[1,5-b][1,2,4]triazines and Tetrazolo[1,5-a]pyrimidines [J].
Deev, Sergey L. ;
Shenkarev, Zakhar O. ;
Shestakova, Tatyana S. ;
Chupakhin, Oleg N. ;
Rusinov, Vladimir L. ;
Arseniev, Alexander S. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8487-8497
[8]   Design and synthesis of novel quinolinone-3-aminoamides and their α-lipoic acid adducts as antioxidant and antiiflammatory agents [J].
Detsi, Anastasia ;
Bouloumbasi, Dionysia ;
Prousis, Kyriakos C. ;
Koufaki, Maria ;
Athanasellis, Giorgos ;
Melagraki, Georgia ;
Afantitis, Antreas ;
Igglessi-Markopoulou, Olga ;
Kontogiorgis, Christos ;
Hadjipavlou-Litina, Dimitra J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (10) :2450-2458
[9]   Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries [J].
Gorobets, NY ;
Yousefi, BH ;
Belaj, F ;
Kappe, CO .
TETRAHEDRON, 2004, 60 (39) :8633-8644
[10]   Synthesis and antimicrobial activity of some novel 4-hydroxyquinolin-2(1H)-ones and pyrano[3,2-c]quinolinones from 3-(1-ethy1-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-3-oxopropanoic acid [J].
Hassanin, Hany Mohamed ;
Ibrahim, Magdy Ahmed ;
Alnamer, Youssef Abdel-Salam .
TURKISH JOURNAL OF CHEMISTRY, 2012, 36 (05) :682-699