Synthesis of morphinans with diversely functionalized benzoxazole moieties

Levente Girán, Zsuzsanna Gyulai, S. Antus, Sándor Berényi, Attila Sipos

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1135-1143
Number of pages9
JournalMonatshefte fur Chemie
Volume141
Issue number10
DOIs
Publication statusPublished - Oct 2010

Fingerprint

Morphinans
Benzoxazoles
Oxazoles
Aminophenols
Hydroxyl Radical
Electrostatics

Keywords

  • Alkaloids
  • Density functional calculations
  • Heterocycles
  • Opioid receptor
  • Palladium-catalyzed direct vinylation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of morphinans with diversely functionalized benzoxazole moieties. / Girán, Levente; Gyulai, Zsuzsanna; Antus, S.; Berényi, Sándor; Sipos, Attila.

In: Monatshefte fur Chemie, Vol. 141, No. 10, 10.2010, p. 1135-1143.

Research output: Contribution to journalArticle

Girán, Levente ; Gyulai, Zsuzsanna ; Antus, S. ; Berényi, Sándor ; Sipos, Attila. / Synthesis of morphinans with diversely functionalized benzoxazole moieties. In: Monatshefte fur Chemie. 2010 ; Vol. 141, No. 10. pp. 1135-1143.
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