Synthesis of pyrano[3,2-c]quinoline-4-carboxylates and 2-(4-oxo-1,4-dihydroquinolin-3-yl)fumarates

被引：27
|
作者：
El-Sheref, Essmat M. [1 ]
Aly, Ashraf A. [1 ]
Mourad, Aboul-Fetouh E. [1 ]
Brown, Alan B. [2 ]
Braese, Stefan [3 ]
Bakheet, Momtaz E. M. [1 ]
机构：
[1] Menia Univ, Fac Sci, Chem Dept, El Minia 61519, Egypt
[2] Florida Inst Technol, Chem Dept, 150 W Univ Blvd, Melbourne, FL 32901 USA
[3] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany
来源：
CHEMICAL PAPERS | 2018年 / 72卷 / 01期
基金：
美国国家科学基金会;
关键词：
2,4(1H,3H)-Quinolinediones; Dialkyl acetylenedicarboxylates; Pyrano[3,2-c]quinolones; Quinolinofumarates; HIV-1; REVERSE-TRANSCRIPTASE; DRUG-RESISTANCE PROPERTIES; DIMETHYL ACETYLENEDICARBOXYLATE; NONNUCLEOSIDE INHIBITORS; RECEPTOR ANTAGONISTS; DESIGN; HETEROCYCLES; DERIVATIVES; QUINOLINE; ACIDS;
D O I：
10.1007/s11696-017-0269-6
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reaction of equimolar amounts of 2,4(1H,3H)-quinolinediones and diethyl acetylenedicarboxylate in absolute ethanol, containing catalytic triethylamine, gave ethyl 5,6-dihydro-2,5-dioxo-6,9-disubstituted-2H-pyrano[3,2-c]quinoline-4-carboxylates in good yields. In a different manner, reaction of two equivalents of dialkyl acetylenedicarboxylates with one equivalent of 2,4(1H,3H)-quinolinediones afforded dialkyl 2(4-oxo-1,4-dihydroquinolin-3-yl)fumarates in good yields. The structures of the products were elucidated by H-1 NMR, C-13 NMR, two-dimensional NMR, IR, mass spectra and elemental analyses. [GRAPHICS] .
引用
收藏
页码：181 / 190
页数：10
相关论文
共 50 条
  • [41] One-pot synthesis of novel 2-(benzofuran-2-yl)-4-phenylquinoline-3-carboxylates
    Gao, Wentao
    Fu, Xinbo
    Zhao, Yanan
    Wang, Dongfang
    JOURNAL OF CHEMICAL RESEARCH, 2017, (01) : 45 - 49
  • [42] Unusual transformation of 4-hydroxy-6-methyl-3-nitro-2H-pyrano[3,2-c] quinoline-2,5(6H)-dione into 1-methyl-4-substituted amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acids
    Badran, Al-Shimaa
    Ibrahim, Magdy A.
    Mostafa, Mai A.
    TETRAHEDRON, 2025, 175
  • [43] SYNTHESIS AND STRUCTURE OF (R,S)-2-METHYL-4-(4-NITROPHENYL)-PYRANO[3,2-c] CHROMEN-5(4H)-ONE
    Nikolova, Rosica P.
    Shivachev, Boris
    Mikhova, Bozhana
    Stamboliyska, Bistra
    Mladenovska, Kristina
    Panovska, Ana P.
    Popovski, Emil
    MACEDONIAN JOURNAL OF CHEMISTRY AND CHEMICAL ENGINEERING, 2013, 32 (02) : 239 - 250
  • [44] Synthesis and Antimicrobial Evaluation of New Pyrano[4,3-b]pyran and Pyrano[3,2-c]chromene Derivatives Bearing a 2-Thiophenoxyquinoline Nucleus
    Makawana, Jigar A.
    Patel, Manish P.
    Patel, Ranjan G.
    ARCHIV DER PHARMAZIE, 2012, 345 (04) : 314 - 322
  • [45] Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
    Bradiakova, Ivana
    Durcekova, Tatiana
    Pronayova, Nada
    Gatial, Anton
    Krutosikova, Alzbeta
    CHEMICAL PAPERS, 2009, 63 (05): : 586 - 591
  • [46] Synthesis of some novel oxazolopyranoquinolinones from 3-amino-4-hydroxypyrano[3,2-c]quinolinedione
    Hassanin, Hany M.
    Abdou, Ibrahim M.
    Saeed, Abdeltawab M.
    ARKIVOC, 2017, : 172 - 186
  • [47] SYNTHESIS OF DIALKYL 2-(DIALKOXYPHOSPHORYL)-3-(4-OXO-4,5-DIHYDRO-THIAZOLE-2-YL SULFANYL) SUCCINATES
    Hassanabadi, Alireza
    Mosslemin, Mohammad H.
    Salari, Shabnam
    Landi, Mahnoush Momeni
    SYNTHETIC COMMUNICATIONS, 2012, 42 (15) : 2309 - 2317
  • [48] One-pot Two-step Reaction for Synthesis of Poly-substituted Pyrano[3,2-c]pyridones and Spiro[indoline-3,4′-pyrano[3,2-c]pyridine]-2,5′(6′H)-diones in Water
    Xu, Zhenhang
    Du, Yijun
    Wang, Songxiang
    Wu, Zeru
    Lou, Yuhao
    Zhang, Furen
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (09) : 2517 - 2527
  • [49] Thermal, Structural, AC Conductivity, and Dielectric Properties of Ethyl-2-amino-6-ethyl-5-oxo-4-(3-phenoxyphenyl)-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate Thin Films
    M. M. El-Shabaan
    Journal of Electronic Materials, 2018, 47 : 5174 - 5182
  • [50] Synthesis of pyrano[3,2-c]quinolones and furo[3,2-c]quinolones via acid-catalyzed tandem reaction of 4-hydroxy-1-methylquinolin-2(1H)-one and propargylic alcohols
    Yin, Haiting
    Wu, Yunjun
    Gu, Xiaoxia
    Feng, Zhijun
    Wang, Meifang
    Feng, Dexiang
    Wang, Ming
    Cheng, Ziyang
    Wang, Shaoyin
    RSC ADVANCES, 2022, 12 (33) : 21066 - 21078
12345