A convenient synthesis of 3-acylindoles via Friedel Crafts acylation of 1-(phenylsulfonyl) indole. A new route to pyridocarbazole-5, 11-quinones and ellipticine
DM Ketcha, GW Gribble
Index: Ketcha, Daniel M.; Gribble, Gordon W. Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5451 - 5457
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Citation Number: 179
Abstract
A Friedel-Crafts acylation of 1-(phenylsulfony1) indoles (1) with carboxylic acid anhydrides and acid chlorides in the presence of aluminum chloride gives 3-acyl-l-(phenylsulfonyl) indoles (2) in 81-99% yields. Base hydrolysis converts 2 to 3-acylindoles (3) in 79-9670 yields. The reaction of 1-(phenylsdfony1) indole (la) with oxalyl chloride gives acid chloride 2h, which is converted to 3-cyanoindole (7) in three steps (75% yield). Although a similar ...
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