Use of chloroalkenylamines for the synthesis of 1-azabicyclo[3.3.0]octane and 1-azabicyclo[4.3.0]nonane derivatives

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Abstract
Various N-(chloroprop-2-enyl)-, N-(3-chlorobut-2-enyl)-, and N-(4-chloropent-3- and -4-enyl)-proline derivatives, -succinimides, and -phthalimides have been synthesised and subjected to Lewis acid treatment. The following gave fruitful results: N-(4-chloropent-3-enyl)-5-hydroxy-2-pyrrolidone (25) gave 1-acetyl-1,2,3,6,7,7a-hexahydropyrrolizin-5-one (28); N-(4-chloropent-3-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (30) gave 1-endo-acetyl-1,2,3,9b-tetrahydropyrrolo[2,1-a] isoindol-5-one (31) which was isomerised to the exo-isomer; N-(4-chloropent-3-enyl)-3-methylene-2,3-dihydro-1H-isoindol-1-one (34) and N-(4-chloropent-3-enyl)-3-hydroxy-3-methyl-2,3-dihydro-1H-isoindol-1-one (33) gave 1-endo-acetyl-9b-methyl-1,2,3,9b-tetrahydropyrrolo[2,1-a]isoindol-5-one(35); N-[-2-(3,4-dimethoxyphenyl)ethyl]proline (42) gave 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinoline (43), N-(2-chloroprop-2-enyl)-2-(2-hydroxy-2-propyl)pyrrolidine (44) gave 6-chloro-8,8-dimethyl-1,2,3,5,8,8a-hexahydroindolizine (47) and 8,8-dimethyl-1,2,3,7,8,8a-hexahydroindolizin-6(5H)-one (48) which were reduced to the corresponding alcohols; N-(4-chloropent-4-enyl)-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (50) gave 7,8,11,11a-hexahydro-5H-azepino[2,1-a]isoindole-5,10(9H)-dione (51).

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