85539-57-7

Upstream product

• 79-04-9 chloroacetyl chloride 
• 1521-51-3 rac-3-bromocyclohexene 
• 100-46-9 benzylamine 
• 141330-12-3 N-benzyl-N-(2-cyclohexenyl)amine 
• 105706-89-6 N-benzyl-2-chloro-N-(cyclohex-2-enyl)acetamide 

Downstream Products

• 85539-64-6 1-Benzyl-1,3,3a,6,7,7a-hexahydro-indol-2-one 
• 85539-65-7 1-Benzyl-4-iodo-octahydro-indol-2-one 
• 85539-66-8 N-benzyl-N-(cyclohex-2-enyl)acetamide 
• 1922-83-4 N-benzyl-hexahydro-oxindole 
• 7135-32-2 1-benzylindolin-2-one 

Relevant academic research and scientific papers

Is an iodine atom almighty as a leaving group for Bu3SnH-mediated radical cyclization? The effect of a halogen atom on the 5-endo-trig radical cyclization of N-vinyl-α-halo amides

The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-halo amides was examined. The cyclization of α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of α-halo amides. The cyclizing ability of α-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an α-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.

New synthesis of heterocycles by use of palladium catalyzed cycli zation of α-haloamide with internal double bond

α-Haloamide having internal double bond was allowed to react with a catalytic amount of Pd(PPh3)4 in the presence of base to produce a cyclized product in a fairly good yield possibly through the intermediate of -alkylmetal complex. By use of this method, five and six membered lactams, pyrrolizidine and quinolizidine derivatives were synthesized in fairly good yields.

CYCLIZATION OF α-HALOAMIDE WITH INTERNAL DOUBLE BOND BY USE OF THE LOW-VALENT METAL COMPLEX

The α-haloamide having internal double bond was allowed to react with a catalytic amount of Pd(PPh3)4 in the presence of proton sponge to produce a cyclized product in a fairly good yield possibly through the intermediation of ?-alkylmetal complex althoug