Amides as precursors of imidoyl radicals in cyclisation reactions
Amides have been successfully used as precursors of imidoyl radicals for radical cyclisation. The amides have been converted to imidoyl selanides via reaction with phosgene to yield imidoyl chlorides followed by reaction with potassium phenylselanide. Imidoyl selanides were reacted with tributyltin hydride (Bu3SnH) as the radical mediator with triethylborane or AIBN as initiators to yield imidoyl radicals for cyclisation reactions. Imidoyl radicals have been cyclised onto alkenes to yield 2,3-substituted-indoles and -quinolines and also onto pyrroles and indoles to give bi- and tricyclic heteroarenes.
Bowman, W. Russell,Fletcher, Anthony J.,Pedersen, Jan M.,Lovell, Peter J.,Elsegood, Mark R.J.,Hernández López, Elena,McKee, Vickie,Potts, Graeme B.S.
p. 191 - 203
(2007/10/03)
Two New Oxindole Syntheses
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)
Cyclodehydration of o-Vinyl Anilides. A General Synthesis of Substituted Quinolines
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Curran, Dennis P.,Kuo, Shen-Chun
p. 2063 - 2065
(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)
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