A convenient approach to the synthesis of dialkyl 5-oxo-1,2-dihydro-5H-chromeno[4,3-b]pyridine-2,3-dicarboxylates

被引:4
|
作者
Glasnov, Toma N. [1 ]
Ivanov, Ivo C. [1 ]
机构
[1] Med Univ Sofia, Fac Pharm, Dept Organ Chem, BG-1000 Sofia, Bulgaria
关键词
annelated ring system; coumarin; enaminoaldehydes; Wittig reaction;
D O I
10.1080/00397910801929465
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Coumarin and its analogs are considered privileged scaffolds in the current synthetic and pharmacological research. The chemical behavior of enaminocarbaldehydes of the coumarin moiety under intramolecular Wittig reaction conditions in the presence of triphenylphosphine and dimethyl or diethyl acetylenedicarboxylates has been studied, resulting in the isolation of a series of dimethyl and diethyl 5-oxo-1,2-dihydro-5H-chromeno[4,3-b]pyridine-2,3-dicarboxylates in good to high yields.
引用
收藏
页码:1579 / 1588
页数:10
相关论文
共 50 条
  • [41] [BMIM][OH]-Mediated One-Pot Synthesis of 2-Amino-5-oxo-4-(1H-pyrazol-5-yl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles as Potential Anticancer Agents
    Srinivas, A.
    Shree, A. Jaya
    Goud, S. Sharath Kumar
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2023, 93 (01) : 227 - 233
  • [42] [BMIM][OH]-Mediated One-Pot Synthesis of 2-Amino-5-oxo-4-(1H-pyrazol-5-yl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles as Potential Anticancer Agents
    A. Srinivas
    A. Jaya Shree
    S. Sharath Kumar Goud
    Russian Journal of General Chemistry, 2023, 93 : 227 - 233
  • [43] Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones
    Maxim R. Demidov
    Anastasiya N. Dobrokvashina
    Dmitry V. Osipov
    Vitaly А. Osyanin
    Yuri N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2021, 57 : 568 - 573
  • [44] Three-component synthesis of 2-acyl-2,3-dihydro-4H-thiochromeno[4,3-b]furan-4-ones and their reductive rearrangement into 4H,5H-thiochromeno[4,3-b]pyran-5-ones
    Demidov, Maxim R.
    Dobrokvashina, Anastasiya N.
    Osipov, Dmitry V.
    Osyanin, Vitaly A.
    Klimochkin, Yuri N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (05) : 568 - 573
  • [45] Synthesis and in vitro evaluation of dihydro-6H-chromeno[4,3-b]isoxazolo[4,5-e]pyridine derivatives as potent antidiabetic agents
    Lingala Suresh
    P. Sagar Vijay Kumar
    P. Onkar
    L. Srinivas
    Y. Pydisetty
    G. V. P. Chandramouli
    Research on Chemical Intermediates, 2017, 43 : 5433 - 5451
  • [46] Synthesis and in vitro evaluation of dihydro-6H-chromeno[4,3-b]isoxazolo[4,5-e]pyridine derivatives as potent antidiabetic agents
    Suresh, Lingala
    Kumar, P. Sagar Vijay
    Onkar, P.
    Srinivas, L.
    Pydisetty, Y.
    Chandramouli, G. V. P.
    RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (10) : 5433 - 5451
  • [47] Efficient Multicomponent Approach to the Medicinally Relevant 5-aryl-chromeno[2,3-b]pyridine Scaffold
    Elinson, Michail N.
    Vereshchagin, Anatoly N.
    Anisina, Yuliya E.
    Egorov, Mikhail P.
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (01) : 108 - 115
  • [48] SYNTHESIS OF 7,7-DIMETHYL-2-PHENYLTETRAHYDROPYRANO(4,3-B)PYRIDINE AND 5,8-DIMETHYL-2-PHENYLTETRAHYDROTIOPYRANO(4,3-B)PYRIDINE
    BARKHUDARYAN, MR
    SAPONDZH.DO
    VARTANYA.SA
    ARMYANSKII KHIMICHESKII ZHURNAL, 1974, 27 (01): : 56 - 60
  • [49] SYNTHESIS OF 2,3-DIHYDRO-5H-OXAZOLO[2,3-B]QUINAZOLIN-5-ONES
    PEET, NP
    ANZEVENO, PB
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (05) : 877 - 880
  • [50] Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
    Jaggavarapu, Satyanarayana Reddy
    Kamalakaran, Anand Solomon
    Jalli, Ventkata Prasad
    Gangisetty, Sravan Kumar
    Ganesh, Munusswamy Ramanujam
    Gaddamanugu, Gopikrishna
    JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (01) : 187 - 195