The Michael addition of indoles to alpha,beta-unsaturated ketones catalyzed by CeCl3.7H2O-NaI combination supported on silica gel.
Alkylation of indoles by means of the Michael addition has been the subject of a number of investigation. It is well established that regioselectivity in the additions of indoles to electron-deficient alkenes is strongly controlled by the reaction medium. In a continuation of the work on developing greener and cleaner technologies, the cerium(III) chloride heptahydrate and sodium iodide combination supported on silica gel catalyzes the alkylation of various indoles with alpha,beta-unsaturated ketones giving 3-(3-oxoalkyl)indole derivatives in good yields. The substitution on the indole nucleus occurred exclusively at the 3-position, and N-alkylation products have not been observed.
Bartoli
Giuseppe
G
Dipartimento di Scienze Chimiche, Università di Camerino, via S. Agostino 1, Italy.
Bartolacci
Massimo
M
Bosco
Marcella
M
Foglia
Gioia
G
Giuliani
Arianna
A
Marcantoni
Enrico
E
Sambri
Letizia
L
Torregiani
Elisabetta
E