Author:
Bell Stephanie E. V.,Brown Roger F. C.,Eastwood Frank W.,Horvath Julianna M.
Abstract
3-Methylideneindolin-2-one (3-methylideneoxindole) (1) was prepared in
60–89% yield by flash vacuum pyrolysis of the acetate or methyl
carbonate of 3-hydroxy-3-methylindolin-2-one, and was fully characterized, but
application of the same procedure to 3-hydroxy-5-methoxyindolin-2-one did not
give useful yields. Cycloaddition reactions of
CH2=
+NR–CH2
– and of the related ylide (25) (from
1-(trimethylsilylmethyl)piperidine-2-carbonitrile and AgF) to
3-methylideneindolin-2-one (1) gave 4–20% yields of spiro
oxindoles, but yields were markedly below those achieved in cycloadditions to
the more electrophilic N-phenylmaleimide (70–79%). Attempted
alkylation of weakly basic secondary amines, e.g. piperidine-2-carbonitrile,
with Me3SiCH2Cl in dimethyl
sulfoxide/K2CO3 gave only
carbamates
Me3SiCH2OOCNR2.
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20 articles.
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