STUDIES ON THE ALKYLATION OF QUINOLIN-2(1H)-ONE DERIVATIVES

被引：3
|
作者：
Chen, Chia-Ling [1 ]
Chen, I-Li [2 ]
Chen, Jih-Jung [2 ]
Wei, Dau-Chang [2 ]
Hsieh, Han-Jie [2 ]
Chang, Ken-Ming [3 ]
Tzeng, Cherng-Chyi [3 ]
Wang, Tai-Chi [2 ]
机构：
[1] KUO Gen Hosp, Dept Pharm, Tainan 700, Taiwan
[2] Tajen Univ, Dept Pharm, Pingtung 907, Taiwan
[3] Kaohsiung Med Univ, Coll Life Sci, Dept Med & Appl Chem, Kaohsiung 807, Taiwan
来源：
JOURNAL OF THE CHILEAN CHEMICAL SOCIETY | 2015年 / 60卷 / 01期
关键词：
N-Alkylation; O-Alkylation; Quinolin-2(1H)-one; METHYLIDENE-GAMMA-BUTYROLACTONES; N-ALKYLATION; O-ALKYLATION; 2-PYRIDONE; INHIBITORS; AGENTS; CATALYSIS;
D O I：
10.4067/S0717-97072015000100008
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkylation of quinolin-2(1H)-one (1) and its C(6) and C(7) substituted dervatives (OMe, OBn, and Cl) with 2-bromoacetophenone or chloroacetone under basic condition (K2CO3 in DMF) gave a mixture of N-1-and O-2-alkylated products with the former one as a major product. However, alkylation of 8-methoxy-, 8-benzyloxy-, and 8-chloro-quinolin-2(1H)-ones under the same reaction conditions gave exclusively O-2-alkylated products.
引用
收藏
页码：2812 / 2816
页数：5
相关论文
共 50 条
  • [31] Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines
    Zaugg, Cornelia
    Schmidt, Gunther
    Abele, Stefan
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (07) : 1003 - 1011
  • [32] A CONVENIENT ONE-STEP SYNTHESIS OF 3-(2-HYDROXYETHYL)-QUINOLIN-2(1H)-ONES
    RAJENDRAN, SP
    ARISVARAN, V
    RAMESH, M
    SHANMUGAM, P
    SYNTHESIS-STUTTGART, 1982, (02): : 160 - 162
  • [33] Spectral characterization and computational studies of some new synthesized 3-arylazo-4-hydroxybenzo[h]quinolin-2(1H )-one dyes
    Mirsadeghi, Fatemeh Ashouri
    Rufchahi, Enayatollah Moradi
    Zarrabi, Saeid
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1268
  • [34] Design, synthesis and pharmacological evaluation of new 3-(1Hbenzimidazol-2-yl)quinolin-2(1H)-one derivatives as potential antitumor agents
    Kuang, Wen-Bin
    Huang, Ri-Zhen
    Qin, Jiao-Lan
    Lu, Xing
    Qin, Qi-Pin
    Zou, Bi-Qun
    Chen, Zhen-Feng
    Liang, Hong
    Zhang, Ye
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 157 : 139 - 150
  • [35] Synthesis and crystal structure of 3-[1-hydroxy-3-oxo-3-(4-methylphenylpropyl)]quinolin-2(1H)-one derivatives
    Lobo, Gricela
    Gonzalez, Teresa
    Briceno, Alexander
    Charris, Jaime
    JOURNAL OF CHEMICAL RESEARCH, 2011, (09) : 509 - 512
  • [36] Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases
    Creaven, Bernadette S.
    Duff, Brian
    Egan, Denise A.
    Kavanagh, Kevin
    Rosair, Georgina
    Thangella, Venkat Reddy
    Walsh, Maureen
    INORGANICA CHIMICA ACTA, 2010, 363 (14) : 4048 - 4058
  • [37] 4-(4-fluorophenyl)-3-(4-pyridyl)quinolin-2(1H)-one
    Peifer, Christian
    Schollmeyer, Dieter
    Selig, Roland
    Laufer, Stefan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O2648 - O2650
  • [38] Studies towards 4-C-Alkylation of Pyridin-2(1H)-one Derivatives
    Tetrahedron, 37 (12505):
  • [39] Synthesis of Trans-4a,12b/3,4-Dihydrodibenzo[f,h]quinolin-2(1H)-Ones and Dibenzo[f,h]quinolin-2(1H)-Ones via Irradiation of 6-Biphenylpyridine-2(1H)-Ones
    Sui, Jingzhi
    He, Yun
    Wang, Tao
    Liang, Yong
    Zhang, Zunting
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (14) : 3554 - 3559
  • [40] 3-(4-fluorophenyl)-4-(4-pyridyl)quinolin-2(1H)-one
    Peifer, C
    Schollmeyer, D
    Laudage, S
    Laufer, S
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2006, 62 : O2475 - O2477
12345