期刊
SYNLETT
卷 -, 期 14, 页码 2135-2138出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2003-42074
关键词
alkaloid; amino acid; arylation; nucleophilic aromatic substitution; steric hindrance; oxindole
A new method for the synthesis of 3-alkyl-3-amino-2-oxindoles is reported. These compounds are prepared in a 3-step procedure using a base-mediated nucleophilic addition of benzylidene-imine protected alpha-aminoesters to 2-nitrofluorobenzene as the key step. The process provides a variety of 3-alkyl-3-amino-2-oxindole analogs in yields of 1-24%. Yields are highest with alanine, phenylalanine and 2-pyridylalanine as the amino acid starting materials, while 3-pyridylalanine and O-methyltyrosine are less efficiently arylated. Sterically hindered amino acids such as valine and phenylglycine are for all practical purposes, not substrates for the key nucleophilic substitution reaction. The resulting 3-alkyl-3-amino- 2-oxindoles are important intermediates for the preparation of drug-like substances. The conversion of alanine ethyl ester to 3-amino-3-methyl-2-oxindole is described.
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