Study on Proline-Catalyzed Facile Synthesis of Novel 3-(α,β-Unsaturated carbonyl)-4-hydroxy-quinolin-2(1H)-ones and Their Fluorescent Properties

被引:0
|
作者
Ye, Jiahai [1 ]
Wu, Jun [2 ]
Huang, Nianfeng [1 ]
Zhang, Wenchao [1 ]
Yu, Shuyan [2 ]
Qin, Zhichun [1 ]
Wang, Zhiyong [1 ]
Shang, Yongjia [2 ]
机构
[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Peoples R China
[2] Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China
关键词
proline; aldol reaction; 4-hydroxy-quinolin-2-one; fluorescence; HIV-1; REVERSE-TRANSCRIPTASE; DRUG-RESISTANCE PROPERTIES; NONNUCLEOSIDE INHIBITORS; ALDOL CONDENSATION; DERIVATIVES; DESIGN; ACID; ANTIOXIDANT; ALKALOIDS;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol reaction of 3-acetyl-4-hydroxy-2(1H)-ones with aromatic aldehydes catalyzed by L-proline was carried out to give novel 3-(alpha,beta-unsaturated carbonyl)-4-hydroxy-2(1H)-ones which were separated from the solvent as pure compounds efficiently. The yields of products were affected by the properties of substitutes in aromatic aldehydes. This result confirmed a new reaction mechanism. The study on the fluorescent properties of some products revealed that this class of compounds is potential fluorescent probes.
引用
收藏
页码:1548 / 1554
页数:7
相关论文
共 31 条
  • [1] Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX
    Abass, M
    Mostafa, BB
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (22) : 6133 - 6144
  • [2] 4-cyano-6,7-dimethoxycarbostyrils with solvent- and pH-independent high fluorescence quantum yields and emission maxima
    Ahvale, Appasaheb B.
    Prokopcova, Hana
    Sefcovicova, Jana
    Steinschifter, Waltraud
    Taeubl, Anna E.
    Uray, Georg
    Stadlbauer, Wolfgang
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 563 - 571
  • [3] 4-substituted-3-phenylquinolin-2(1H)-ones: Acidic and nonacidic glycine site N-methyl-D-aspartate antagonists with in vivo activity
    Carling, RW
    Leeson, PD
    Moore, KW
    Moyes, CR
    Duncton, M
    Hudson, ML
    Baker, R
    Foster, AC
    Grimwood, S
    Kemp, JA
    Marshall, GR
    Tricklebank, MD
    Saywell, KL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (05) : 754 - 765
  • [4] TOTAL SYNTHESIS OF PHENOLIC BALFOURODENDRON ALKALOIDS
    CORRAL, RA
    ORAZI, OO
    AUTINO, JC
    [J]. TETRAHEDRON LETTERS, 1983, 24 (23) : 2359 - 2360
  • [5] Facile Stereoselective Synthesis of Fluorinated Flavanone Derivatives via a One-Pot Tandem Reaction
    Cui, Haifeng
    Li, Peng
    Chai, Zhuo
    Zheng, Changwu
    Zhao, Gang
    Zhu, Shizheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03): : 1400 - 1402
  • [6] Discovery and structure-activity relationship studies of a unique class of HIV-1 integrase inhibitors
    Dayam, Raveendra
    Sanchez, Tino
    Neamati, Nouri
    [J]. CHEMMEDCHEM, 2006, 1 (02) : 238 - 244
  • [7] Design and synthesis of novel quinolinone-3-aminoamides and their α-lipoic acid adducts as antioxidant and antiiflammatory agents
    Detsi, Anastasia
    Bouloumbasi, Dionysia
    Prousis, Kyriakos C.
    Koufaki, Maria
    Athanasellis, Giorgos
    Melagraki, Georgia
    Afantitis, Antreas
    Igglessi-Markopoulou, Olga
    Kontogiorgis, Christos
    Hadjipavlou-Litina, Dimitra J.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (10) : 2450 - 2458
  • [8] FERRER P, 1995, LIEBIGS ANN, P1895
  • [9] Design of non-nucleoside inhibitors of HIV-1 reverse transcriptase with improved drug resistance properties. 2.
    Freeman, GA
    Andrews, CW
    Hopkins, AL
    Lowell, GS
    Schaller, LT
    Cowan, JR
    Gonzales, SS
    Koszalka, GW
    Hazen, RJ
    Boone, LR
    Ferris, RG
    Creech, KL
    Roberts, GB
    Short, SA
    Weaver, K
    Reynolds, DJ
    Milton, J
    Ren, JS
    Stuart, DI
    Stammers, DK
    Chan, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) : 5923 - 5936
  • [10] A REVERSIBLE CLAISEN REARRANGEMENT OF 3-(3,3-DIMETHYLALLYL)-4-(3,3-DIMETHYLALLYLOXY)QUINOLIN-2-ONE - SYNTHESIS OF BUCHAPSINE AND LOSS OF ITS 1,1-DIMETHYLALLYL GROUP
    GRUNDON, MF
    RAMACHANDRAN, VN
    [J]. TETRAHEDRON LETTERS, 1985, 26 (35) : 4253 - 4256