A three-component, one-pot synthesis of 1,8-naphthyridine and isoxazole derivatives and computational elucidation of the mechanism

被引:4
作者
Guleli, Muge [1 ]
Erdem, Safiye S. [2 ]
Ocal, Nuket [1 ]
Erden, Ihsan [3 ]
Sari, Ozlem [4 ]
机构
[1] Yildiz Tech Univ, Dept Chem, Fac Arts & Sci, Davutpasa Campus, TR-34220 Esenler, Turkey
[2] Marmara Univ, Dept Chem, Fac Arts & Sci, TR-34722 Istanbul, Turkey
[3] San Francisco State Univ, Dept Chem & Biochem, 1600 Holloway Ave, San Francisco, CA 94132 USA
[4] Kirsehir Ahi Evran Univ, Dept Chem, TR-40100 Kirsehir, Turkey
基金
美国国家卫生研究院;
关键词
Isoxazoles; 1,8-Naphthyridines; Catalyst; Conjugated heterocycles; Computational studies; PATH; AROMATICITY; CONTINUUM; OXIDATION; KINETICS; ANALOGS;
D O I
10.1007/s11164-018-03721-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and general method for the synthesis of substituted 3,4-dimethylisoxazolo[5,4-b]pyridine-5-carboxamide and benzo[b][1,8]naphthyridine-3-carboxamide derivatives by using 2,2,6-trimethyl-4H-1,3-dioxin-4-one, benzyl amine, aromatic aldehydes, 2-aminoquinoline, or 5-amino-3-methylisoxazole in the presence of a catalytic amount of p-toluenesulfonic acid or iodine is described. The formation of the products was investigated and the results obtained were also supported by theoretical calculations.
引用
收藏
页码:2119 / 2134
页数:16
相关论文
共 25 条
  • [1] Computational modeling of the direct hydride transfer mechanism for the MAO catalyzed oxidation of phenethylamine and benzylamine: ONIOM (QM/QM) calculations
    Akyuz, Mehmet Ali
    Erdem, Safiye Sag
    [J]. JOURNAL OF NEURAL TRANSMISSION, 2013, 120 (06) : 937 - 945
  • [2] Synthesis and evaluation of pyrazolo[3,4-b] pyridines and its structural analogues as TNF-α and IL-6 inhibitors
    Bharate, Sandip B.
    Mahajan, Tushar R.
    Gole, Yogesh R.
    Nambiar, Mahesh
    Matan, T. T.
    Kulkarni-Almeida, Asha
    Balachandran, Sarala
    Junjappa, H.
    Balakrishnan, Arun
    Vishwakarma, Ram A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) : 7167 - 7176
  • [3] ONIOM calculations on serotonin degradation by monoamine oxidase B: insight into the oxidation mechanism and covalent reversible inhibition
    Cakir, Kubra
    Erdem, Safiye Sag
    Atalay, Vildan Enisoglu
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (39) : 9239 - 9252
  • [4] Nucleus-independent chemical shifts (NICS) as an aromaticity criterion
    Chen, ZF
    Wannere, CS
    Corminboeuf, C
    Puchta, R
    Schleyer, PV
    [J]. CHEMICAL REVIEWS, 2005, 105 (10) : 3842 - 3888
  • [5] Investigation on the aromaticity of 1,3,4-thiadiazole-2-thione and its oxygen analogs including their tautomeric forms
    Erdem, SS
    Özpinar, GA
    Saçan, MT
    [J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2005, 726 (1-3): : 233 - 243
  • [6] Frisch M. J., 2010, GAUSSIAN 09 REVISION
  • [7] THE PATH OF CHEMICAL-REACTIONS - THE IRC APPROACH
    FUKUI, K
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) : 363 - 368
  • [8] REACTION-PATH FOLLOWING IN MASS-WEIGHTED INTERNAL COORDINATES
    GONZALEZ, C
    SCHLEGEL, HB
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) : 5523 - 5527
  • [9] AN IMPROVED ALGORITHM FOR REACTION-PATH FOLLOWING
    GONZALEZ, C
    SCHLEGEL, HB
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (04) : 2154 - 2161
  • [10] Synthesis of stable tetrahedral intermediates (hemiaminals) and kinetics of their conversion to thiazol-2-imines
    Gunal, Sule Erol
    Gurses, Gulben Sabuncu
    Erdem, Safiye Sag
    Dogan, Ilknur
    [J]. TETRAHEDRON, 2016, 72 (17) : 2122 - 2131