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 [J].
Akyuz, Mehmet Ali ;
Erdem, Safiye Sag .
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 [J].
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. .
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 [J].
Cakir, Kubra ;
Erdem, Safiye Sag ;
Atalay, Vildan Enisoglu .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (39) :9239-9252
[4]   Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].
Chen, ZF ;
Wannere, CS ;
Corminboeuf, C ;
Puchta, R ;
Schleyer, PV .
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 [J].
Erdem, SS ;
Özpinar, GA ;
Saçan, MT .
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 [J].
FUKUI, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :363-368
[8]   REACTION-PATH FOLLOWING IN MASS-WEIGHTED INTERNAL COORDINATES [J].
GONZALEZ, C ;
SCHLEGEL, HB .
JOURNAL OF PHYSICAL CHEMISTRY, 1990, 94 (14) :5523-5527
[9]   AN IMPROVED ALGORITHM FOR REACTION-PATH FOLLOWING [J].
GONZALEZ, C ;
SCHLEGEL, HB .
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 [J].
Gunal, Sule Erol ;
Gurses, Gulben Sabuncu ;
Erdem, Safiye Sag ;
Dogan, Ilknur .
TETRAHEDRON, 2016, 72 (17) :2122-2131