A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.
[reaction--see text] Indoles are selectively acylated at the 3-position in high yields on treatment with a wide variety of acyl chlorides in CH(2)Cl(2) in the presence of diethylaluminum chloride or dimethylaluminum chloride. The reaction proceeds under mild conditions and is applicable to indoles bearing various functional groups without NH protection.
Okauchi
T
T
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1, Sensuicho, Tobata, Kitakyushu, 804-8550, Japan. okauchi@che.kyutech.ac.jp
Itonaga
M
M
Minami
T
T
Owa
T
T
Kitoh
K
K
Yoshino
H
H
D000215:Acylation; D000473:Alkanes; D000535:Aluminum; D002712:Chlorides; D015195:Drug Design; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009942:Organometallic Compounds
D000473:Alkanes; D002712:Chlorides; D007202:Indicators and Reagents; D007211:Indoles; D009942:Organometallic Compounds; D000535:Aluminum