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Synthesis of morphinans with diversely functionalized benzoxazole moieties

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Abstract

Three independent strategies have been established for the synthesis of morphinans with oxazole moieties derived from the aminophenol function of 2-aminomorphine. All the procedures possess the ability to furnish diversely substituted 2′-oxazole moieties which are considered significant in view of the presented density functional studies on the spatial and electrostatic properties of the proximal functions of the 3-hydroxyl of the morphinan backbone. These data are considered important for neuropharmacological development of potential kappa antagonist morphinans. The second strategy was extended to the direct vinylation of oxazoles to form more complex benzoxazole-type morphinans.

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Acknowledgments

The authors are grateful to the National Science Foundation (Grant OTKA reg. no. K81701) for the financial support.

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Author notes

  1. Attila Sipos

    Present address: Department of Pharmaceutical Chemistry, University of Debrecen, P.O. Box 70, Debrecen, 4010, Hungary

Authors and Affiliations

  1. Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary

    Levente Girán, Zsuzsanna Gyulai, Sándor Antus, Sándor Berényi & Attila Sipos

  2. Research Group for Carbohydrates of the Hungarian Academy of Sciences, P.O. Box 55, Debrecen, 4010, Hungary

    Sándor Antus

Authors
  1. Levente Girán
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  2. Zsuzsanna Gyulai
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  3. Sándor Antus
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  4. Sándor Berényi
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  5. Attila Sipos
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Corresponding author

Correspondence to Attila Sipos.

Additional information

Dedicated to Prof. Sándor Makleit to mark his 80th birthday.

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Girán, L., Gyulai, Z., Antus, S. et al. Synthesis of morphinans with diversely functionalized benzoxazole moieties. Monatsh Chem 141, 1135–1143 (2010). https://doi.org/10.1007/s00706-010-0380-7

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  • DOI: https://doi.org/10.1007/s00706-010-0380-7

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