Abstract
The formation of 1-aryl-2,3,4,5-tetrahydro-1H-3-benzazepine can be carried out by condensation between a phenethylamine and aryl and/or hetaryl-oxiranes, followed by cyclisation of the formed alcohol. Several classical methods allow the preparation of aryl oxiranes but when applied to benzo-fused heterocycles, the results are dramatically different clearly showing the lack of comparative studies on this topic. The versatility of the use of trimethylsulfonium chloride, under basic conditions, for the formation of aryl and/or hetaryl-oxiranes has been clearly demonstrated in this work.
Highlights
Dopamine receptors have been implicated in neuropsychiatric disorders and it has been established[1] that SCH-23390 and related benzazepine derivatives are highly selective D1 dopamine antagonists
Several synthetic preparations of aryl-oxiranes are given in the literature and can be classified in two main groups : - the oxidation of a vinyl aromatic compound, and - the methylene addition to an aromatic aldehyde or ketone
The most generally described method for the formation of aryl oxiranes consists of reacting an aldehyde or a ketone with Corey’s reagent 3a formed from a trimethylsulfoxonium salt, or its equivalent 3b (Corey−Chaykovsky’s reagent), which was prepared from a trimethylsulfoxonium salt
Summary
Dopamine receptors have been implicated in neuropsychiatric disorders and it has been established[1] that SCH-23390 and related benzazepine derivatives are highly selective D1 dopamine antagonists. We decided to prepare such benzazepines bearing a heterocycle, instead of a phenyl group, in order that they could be labeled in a final step for in vivo imaging experiments: benzo[b]furan and thiophene rings, linked to the benzazepine at the seven-membered ring, were chosen. One of the well documented synthetic methods[1−3] used for the preparation of these 1-aryl2,3,4,5-tetrahydro-1H-3-benzazepines 1 is based on the condensation of the appropriate phenethylamine with an aryl oxirane 2
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