Research Article

Facile Iodine-Catalyzed Michael Addition of Indoles to , -Bis(arylmethylene)cyclopentanones: An Efficient Synthesis of E-2-(3-Indolylphenylmethyl)-5-phenylmethylenecyclopentanones

Table 2

Results of Michael addition of indoles to α,α′-bis(arylmethylene)cyclopentanones catalyzed by iodine.

674629.table.002

EntryArRProductTime (h)Yielda (%)M.p. (°C)

1C6H5H3a460
215-216
24-CH3-C6H4H3b465
202-203
34-Cl-C6H4H3c375
208-209
44-Br-C6H4H3d3.570
209-210
5C6H5CH33e468
70–72
64-CH3-C6H4CH33f575
170–172
74-Cl-C6H4CH33g4.580
94-95
84-CH3O-C6H4H or CH310b
93,4-(CH3O)2-C6H3H or CH310b
102-furylH or CH310b

aYield after column chromatography.
bThe resulting crude material obtained after this time was mainly the starting compounds.