Two oxindole syntheses are described, both starting from ketones, in which the carbonyl carbon becomes C-3 of the oxindole.The first route uses o-lithioformanilide followed by attack with cyanide ion and hydrolysis.The second uses a pinacol-type rearragement (or the γ-silyl alcohol variation) to create the quaternary centre, and involves an intramolecular displacement of fluoride ion from an unactivated benzene ring by an amide nitrogen to complete the lactam ring.The two routes are stereochemically complementary, giving different spiro-oxindoles from norbornanone.
Fleming, Ian,Loreto, Maria Antonietta,Wallace, Ian H.M.,Michael, Joseph P.
p. 349 - 360
(2007/10/02)
TWO NEW STEREOCHEMICALLY COMPLEMENTARY OXINDOLE SYNTHESES
Two routes have been developed for the conversion of ketones to oxindoles in the general sense (3->4); with norbornanone, the two routes gave different oxindoles (22 and 24).
Fleming, Ian,Loreto, Maria Antonietta,Michael, Joseph P.,Wallace, Ian H. M.
p. 2053 - 2056
(2007/10/02)
More Articles about upstream products of 82757-18-4