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Structural Chemistry

, Volume 28, Issue 3, pp 773–790 | Cite as

Experimental and theoretical investigation of new furan and thiophene derivatives containing oxazole, isoxazole, or isothiazole subunits

  • Pervin Ünal Civcir
  • Gülbin Kurtay
  • Kübra Sarıkavak
Original Research

Abstract

Herein, we present joint experimental and theoretical studies on newly designed thiophene- or furan-based oxazole, isoxazole, and isothiazole derivatives. Our synthetic approach towards the preparation of target compounds is based on Van Leusen reaction. By following this reaction, oxazoles (1 and 2) containing the pertinent heterocyclic systems were obtained from the reaction of suitable furan or thiophene derivatives with tosylmethyl isocyanide (TOSMIC). Hereby, three ring systems of furan or thiophene, linked to the oxazole rings at their 2- and 5-positions (3 and 4), were also successfully synthesized for the first time. Reaction of the starting materials containing acetyl groups in their 2-position with dimethyl acetal and following the treatment by hydroxylamine hydrochloride, desired isoxazole derivatives (5 and 6), were obtained. Additionally, isothiazole derivatives (7 and 8) were prepared by following the similar approach to the isoxazole synthesis. Whole of these cyclization reactions occurred with good to excellent yields. Structural analyses of the synthesized compounds were performed by appropriate spectroscopic methods (UV-vis, FT-IR, LC-MS, 1H-NMR, 13C-NMR, and elemental analysis). We also carried out theoretical studies for identifying the structure-activity relationship and determining chemical properties of the studied molecules. For this purpose, we obtained information about structural properties (bond lengths, bond angles, dihedral angles, and dipole moments), band gap energies, and spectroscopic characteristics (UV-vis, FT-IR, 1H-NMR, and 13C-NMR) of the target compounds.

Graphical abstract

Keywords

Oxazole Isoxazole Isothiazole Thiophene Furan DFT 

Notes

Acknowledgments

Pervin Ünal Civcir would like to express her gratitude to AU-BAP (Project No: 13H4240002) for financial support. The numerical calculations reported in this research were performed at TUBITAK-ULAKBİM. High Performance and Grid Computing Center (TR-Grid e-Infrastructure).

Supplementary material

11224_2016_863_MOESM1_ESM.pptx (5.8 mb)
ESM 1 (PPTX 5927 kb)
11224_2016_863_MOESM2_ESM.pptx (9 mb)
ESM 2 (PPTX 9202 kb)

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© Springer Science+Business Media New York 2016

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceAnkara UniversityAnkaraTurkey

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