An efficient route to 3-aryl-substituted quinolin-2-one and 1,8-naphthyridin-2-one derivatives of pharmaceutical interest

被引：28
|
作者：
Mitsos, CA [1 ]
Zografos, AL [1 ]
Igglessi-Markopoulou, O [1 ]
机构：
[1] Natl Tech Univ Athens, Sch Chem Engn, Organ Chem Lab, GR-15773 Athens, Greece
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期
关键词：
D O I：
10.1021/jo0340051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of arylacetic ester enolates with 2-alkoxy-4H-3,1-benzoxazin-4-ones offers a short and versatile synthetic route to 3-aryl-4-hydroxyquinolin-2(1H)-ones, through the cyclization of the beta-ketoesters produced. Similar reactions of 4H-pyrido[2,3-d][1,3]oxazin-4-ones with ester enolates afford 1-acyl-4-hydroxy-1,8-naphthyridin-2(1H)-ones in a convenient two-step, one-pot procedure.
引用
收藏
页码：4567 / 4569
页数：3
相关论文
共 50 条
  • [1] SOME REACTIONS OF 3-FORMYL-1,8-NAPHTHYRIDIN-2-ONE
    MOHAMED, EA
    ABDELRAHMAN, RM
    ELGENDY, Z
    ISMAIL, MM
    ANALES DE QUIMICA, 1993, 89 (02): : 246 - 253
  • [2] New route synthesis of some quinolin-2-one derivatives
    Soleiman, HA
    CHEMICAL PAPERS-CHEMICKE ZVESTI, 2004, 58 (05): : 330 - 333
  • [3] Discovery of 1,8-naphthyridin-2-one derivative as a potent and selective sphingomyelin synthase 2 inhibitor
    Yukawa, Takafumi
    Nakahata, Takashi
    Okamoto, Rei
    Ishichi, Yuji
    Miyamoto, Yasufumi
    Nishimura, Satoshi
    Oikawa, Tatsuo
    Kubo, Kazuki
    Adachi, Ryutaro
    Satomi, Yoshinori
    Nakakariya, Masanori
    Amano, Nobuyuki
    Kamaura, Masahiro
    Matsunaga, Nobuyuki
    BIOORGANIC & MEDICINAL CHEMISTRY, 2020, 28 (07)
  • [4] Synthesis and antiproliferative activity of pyrrolo[2,3-b]pyridine derivatives bearing the 1,8-naphthyridin-2-one moiety
    Tang, Qidong
    Duan, Yongli
    Wang, Linxiao
    Wang, Min
    Ouyang, Yiqiang
    Wang, Caolin
    Mei, Han
    Tang, Sheng
    Xiong, Yinhua
    Zheng, Pengwu
    Gong, Ping
    Zhu, Wufu
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 : 266 - 275
  • [5] Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 1,8-naphthyridin-2-one moiety
    Tang, Qidong
    Duan, Yongli
    Xiong, Hehua
    Chen, Ting
    Xiao, Zhen
    Wang, Linxiao
    Xiao, Yueyue
    Huang, Shunmin
    Xiong, Yinhua
    Zhu, Wufu
    Gong, Ping
    Zheng, Pengwu
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 158 : 201 - 213
  • [6] One-pot Synthesis of 3-Aryl-substituted 1-Hydroxy-2-acylindolizines
    Kloubert, Tobias
    Kretschmer, Robert
    Goerls, Helmar
    Krieck, Sven
    Westerhausen, Matthias
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2012, 67 (11): : 1151 - 1158
  • [7] A new approach to the synthesis of polyfunctionally substituted 1,8-naphthyridin-2-one derivatives from 6-azidopyridones: A novel thermal decomposition to 6-aminopyridones
    Mekheimer, RA
    SYNTHESIS-STUTTGART, 2001, (01): : 103 - 107
  • [8] Synthesis and antibacterial activity screening of N-and O-substituted quinolin-2-one acetamide derivatives
    Chand, Karam
    Yadav, Preeti
    Prasad, Suchita
    Sharma, Sunil K.
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2017, 56 (12): : 1243 - 1250
  • [9] Interaction of fluorescent quinolin-2-one and coumarin derivatives including dipeptides with lipid bilayers
    Abreu, Ana S.
    Hermenegildo, Bruno F. C.
    Ferreira, Paula M. T.
    Queiroz, Maria Joao R. P.
    Castanheira, Elisabete M. S.
    RSC ADVANCES, 2016, 6 (76): : 72141 - 72148
  • [10] Synthesis and Biological Activities of Novel Triazolesulfonamide Derivatives Containing Quinolin-2-one Moiety
    Cheng, Hua
    Wang, Wanqiang
    Huang, Lin
    Cui, Ping
    Wu, Qiongyou
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (05) : 1065 - 1072
12345