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

  • Muge Guleli
  • Safiye S. ErdemEmail author
  • Nuket OcalEmail author
  • Ihsan ErdenEmail author
  • Ozlem Sari
Article
  • 25 Downloads

Abstract

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.

Keywords

Isoxazoles 1,8-Naphthyridines Catalyst Conjugated heterocycles Computational studies 

Notes

Acknowledgements

N. Ocal gratefully acknowledges financial support of this work by the Scientific and Technological Research Council of Turkey (TUBITAK, project no. 112T880). I. Erden acknowledges financial support of this work by funds from the National Institutes of Health (grant no. SC1GM082340). The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

Supplementary material

11164_2018_3721_MOESM1_ESM.pdf (3.3 mb)
Supplementary material 1 (PDF 3384 kb)

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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Faculty of Arts and Sciences, Department of ChemistryYildiz Technical UniversityEsenler-IstanbulTurkey
  2. 2.Faculty of Arts and Sciences, Chemistry DepartmentMarmara UniversityGoztepe, IstanbulTurkey
  3. 3.Department of Chemistry and BiochemistrySan Francisco State UniversitySan FranciscoUSA
  4. 4.Department of ChemistryKırsehir Ahi Evran UniversityKırsehirTurkey

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