Synthesis of 1-azabicyclo〔x,y,O〕alkanediones

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  • Synthesis of 1-Azabicyclo [x, y, 0] alkanediones.
  • Synthesis of 1-azabicyclo x , y , O alkanediones

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4-Phenyl-3-butenyl-and 5-phenyl-4-pentenyl-amine were acylated with chloride of methyl hydrogen succinate, glutarate and adipate yielding six kinds of ester amide (VIIa, b, c, d, e, f), all of which except (VIId) were cyclized with ease on being treated with POCl3 in boiling benzene, giving three pyrrolines (VIIIa, b, c) and two hydropyridines (VIIIe, f). These were reduced and each were converted into the corresponding lactams (Xa, b, c, e, f), from which benzylidene group was removed by ozonization furnishing 5 kinds of title compounds (XIa, b, c, e, f). Their structures were supported by converting one (XIe) of them to the known 1-quinolizidinone, which was identified with the authentic specimen.

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