A direct access to 3-(2-Oxoalkyl)indoles via aluminum chloride induced C-C bond formation.
3-Methylindole is acylated regioselectively at the methyl group when treated with a variety of acyl chlorides in 1,2-dichloroethane in the presence of AlCl(3), affording a mild and direct method for the synthesis of 3-(2-oxoalkyl)indoles. The product formation in this one-pot reaction largely depends on the conditions of the reaction employed. The methodology does not require protection-deprotection steps and is amenable for the scale-up synthesis of these indole derivatives.
Pal
Manojit
M
Chemistry-Discovery Research, Dr. Reddy's Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500049, India manojitpal@drreddys.com
Dakarapu
Rambabu
R
Padakanti
Srinivas
S
D000215:Acylation; D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012862:Skatole / Q000138:chemical synthesis / Q000737:chemistry
D017607:Aluminum Compounds; D002712:Chlorides; D006843:Hydrocarbons, Chlorinated; D007211:Indoles; D000077410:Aluminum Chloride; D002244:Carbon; D012862:Skatole