- Expedient Pd-Catalyzed α-Arylation towards Dibenzoxepinones: Pivotal Manske's Ketone for the Formal Synthesis of Cularine Alkaloids
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The general synthesis of diversely substituted dibenzoxepinones by a combined Pd-catalyzed α-arylation and SNAr strategy is reported and applied to the synthesis of Manske's ketone, a key intermediate en route to the total synthesis of cularine alkaloids. In the course of this work, an unanticipated ring contraction reaction to a xanthone was observed and serves as a caveat for the conditions of the widely used α-arylation reaction.
- Deichert, Julie A.,Mizufune, Hideya,Patel, Jignesh J.,Hurst, Timothy E.,Maheta, Ashish,Kitching, Matthew O.,Ross, Avena C.,Snieckus, Victor
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p. 4693 - 4697
(2020/05/08)
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- Affinity of 10-(4-Methylpiperazino)dibenzoxepins for Clozapine and Spiroperidol Binding Sites in Rat Brain
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10-(4-Methylpiperazino)dibenzoxepins were prepared and evaluated as potential antipsychotic agents using specific clozapine diazepine> binding sites in rat forebrain that are noncholinergic and nondopaminergic in nature and from which clozapine is displaced by known antipsychotic agents. Clozapine binding in the presence of atropine represents nonmuscarinic binding, while binding in the absence of atropine represents muscarinic (cholinergic) plus nonmuscarinic binding.The relative affinity for dopamine binding sites was determined by displacement of spiroperidol from binding sites in rat caudate nuclei.Thus, clozapine, its 2-chloro isomer, its dechloro analogue, and their 5H-dibenzocycloheptene and dibenzoxepin analogues have about the same relative affinity for the nonmuscarinic clozapine binding sites.At the spiroperidol (dopaminergic) sites, both the nature of the tricyclic system and the presence of chlorine atom on the tricyclic system have a substantial effect on the binding affinity.Within each series, shift of a chlorine atom from the position distal to the piperazino group to the proximal position increases the binding affinity by a factor of about nine, but removal of the chlorine atom substantially decreases the binding affinity.Nevertheless, 10-(4-methylpiperazino)dibenzoxepin has a threefold greater affinity for the dopaminergic binding sites than does clozapine itself.
- Harris, Terry W.,Smith, Howard E.,Mobley, Philip L.,Manier, D. Hal,Sulser, Fridolin
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p. 855 - 858
(2007/10/02)
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- Coated 1-(2-chlorodibenzo[b,f]oxepin-10-yl)-4-methylpiperazine compositions
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A coated 1-(2-chlorodibenzo[b,f]oxepin-10-yl)-4-methylpiperazine composition, suitable for pharmaceutical use.
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- Dibenz[b,f]oxepin derivatives
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Dibenz[b,f]oxepins of the formula STR1 wherein R, R1, R2, R3 and R4 are as hereinafter described. The foregoing compounds exhibit strong central depressant and neuroleptic properties, and are useful, for example
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