Novel aryloxy-8-azabicyclo[3.2.1]oct-3-enes with 5-HT transporter and 5-HT1A affinity

Gilbert, Adam M.; Coleman, Thomas R.; Kodah, Jason; Mewshaw, Richard E.; Scerni, Rosemary; Schechter, Lee E.; Smith, Deborah L.; Andree, Terrance H.

doi:10.1016/j.bmcl.2004.08.030

Cited by 9 publications

(2 citation statements)

References 16 publications

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“…To our knowledge, none of the organic γ-substituted cyclohexenones reported in this paper have been previously synthesized. However, 33 closely resembles an advanced synthetic intermediate patented for use as an antidepressant . In most cases, naphthalene undergoes electrophilic addition reactions preferentially at the 1-position.…”

Section: Resultsmentioning

confidence: 99%

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Friedel–Crafts Ring-Coupling Reactions Promoted by Tungsten Dearomatization Agent

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The complexes TpW(NO)(PMe 3 )(L), where L = phenol, N,N-dimethylanilinium, or naphthalene, undergo protonation followed by addition of an aromatic nucleophile. The addition of aromatic molecules occurs at the para carbon of the phenol or aniline ring or the beta carbon of the naphthalene. The addition occurs anti to the metal fragment, as determined by X-ray crystallography. In the case where L = phenol or N,N-dimethylanilinium, treatment of the bound arene with an electrophilic heteroatom followed by an aromatic nucleophile sets two stereocenters, with both additions occurring anti to the metal. The resultant ligands have been removed from the metal by oxidative decomplexation using ceric ammonium nitrate.

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Section: Resultsmentioning

confidence: 99%

“…However, 33 closely resembles an advanced synthetic intermediate patented for use as an antidepressant. 28 In most cases, naphthalene undergoes electrophilic addition reactions preferentially at the 1-position. However, under thermodynamic control or in the presence of a bulky electrophile, 2substitution is preferred.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Friedel–Crafts Ring-Coupling Reactions Promoted by Tungsten Dearomatization Agent

et al. 2013

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