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Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide

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Abstract

A series of benzyloxybenzaldehyde derivatives (1–3) were prepared by the reactions of 4-nitrobenzyl bromide with 4-hydroxy-3-methoxybenzaldehyde (vanillin), 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and 2-hydroxy-4-methoxybenzaldehyde. When the reaction time is quite long, benzofuran derivatives (4 and 5) were obtained by the reactions of ortho-hydroxyaldehydes with the 4-nitrobenzyl bromide. Condensation reactions among the three benzyloxybenzaldehyde derivatives (1–3) with 2-aminomethylfuran (furfurylamine) yielded the new imine compounds (6–8). The structures of these aldehydes (1–3), benzofuran derivatives (4 and 5) and imine compounds (6–8) were confirmed on the basis of elemental analyses, IR, 1H NMR and 13C NMR and mass spectroscopy. The solid-state structures of compounds 4–6 were determined by single-crystal X-ray crystallography.

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Acknowledgements

The authors gratefully acknowledge the financial assistance of the Scientific and Technical Research Council of Turkey (TUBITAK), Grand No. TBAG 109T034. We also thank Anadolu University and Medicinal Plants and Medicine Research Center of Anadolu University Eskişehir, for allowing us to use the X-ray facility.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ankara University, 06100, Ankara, Turkey

    Zeliha Hayvali, Pinar Köksal & Duygu Şahin

  2. Department of Chemistry, Faculty of Science, Anadolu University, 26470, Eskisehir, Turkey

    Hakan Dal

  3. Department of Physics, Hacettepe University, 06800, Ankara, Turkey

    Tuncer Hökelek

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  1. Zeliha Hayvali
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  2. Hakan Dal
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  3. Pinar Köksal
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  4. Duygu Şahin
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  5. Tuncer Hökelek
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Correspondence to Zeliha Hayvali.

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Hayvali, Z., Dal, H., Köksal, P. et al. Syntheses, spectroscopic and crystallographic characterizations of 4-nitrobenzyloxy derivatives and benzofurans from ortho-substituted benzaldehydes and 4-nitrobenzyl bromide. Struct Chem 21, 837–845 (2010). https://doi.org/10.1007/s11224-010-9618-6

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