63838-27-7

Upstream product

• 94893-89-7 N-(4-chloropent-3-enyl)-5-hydroxy-2-pyrrolidone 
• 63838-19-7 1-(3-pentynyl)-5-ethoxy-pyrrolidone-2 
• 20177-02-0 2,5-dichloro-2-pentene 
• 63838-13-1 1-Pent-3-ynyl-pyrrolidine-2,5-dione 
• 10229-10-4 pent-3-yn-1-ol 
• 94893-87-5 N-(4-chloropent-3-enyl)succinimide 
• 24156-99-8 5-bromo-2-chloropent-2-ene 
• 20518-51-8 2-chloropent-2-en-5-ol 
• 5891-21-4 5-chloro-2-pentanone 

Relevant academic research and scientific papers

Use of Chloroalkenylamines for the Synthesis of 1-Azabicyclooctane and 1-Azabicyclononane Derivatives

Various N-(chloroprop-2-enyl)-, N-(3-chlorobut-2-enyl)-, 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-tetrahydropyrroloisoindol-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-tetrahydropyrroloisoindol-5-one (35); N-proline (42) gave 8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrroloisoquinoline (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-tetrahydro-5H-azepinoisoindole-5,10(9H)-dione (51).

α-ACYLIMINIUM ION-ACETYLENE CYCLISATIONS

Cyclisation of acetylenic ethoxylactams 1b-12b leads to bridgehead nitrogen bicyclic ketones in excellent yields.The reaction is weakly acid-catalysed and proceeds at ambient temperature.The observed regioselectivity effect is discussed in terms of stability of exo vs endo vinyl cations and ring strain effects.The high yield conversion of N-(5-hexynyl)-ethoxy lactams 7b and 8b in the 5/8 and 6/8 fused bicyclic ketolactams 7c and 8c deserves special attention.