KHSO4-Assisted Michael Addition–Elimination Reactions of Indole with 3-Dimethylamino-1-phenylprop-2-en-1-ones in Water: An Environmentally Friendly Synthesis of Novel 3-Indolylchalcones

Abstract

KHSO4-assisted Michael addition–elimination reactions of 2-methylindoles and 1,2-dimethylindoles with 3-dimethylamino-1-phenylprop-2-en-1-ones (2) in water, leading to the formation of 3-(2-methyl-1H-indol-3-yl)-1-arylpropenones (3a–e) and 3-(1,2-dimethy-1H-lindol-3-yl)-1-arylpropenones (3f–j) respectively in good to excellent yields have been reported. However, cyclodehydration of adducts 3a–f to give carbazoles 4 failed to take place under the reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.