Simple synthesis of dialkyl 2-(3-oxo-3H-indol-2-yl)-but-2-enedioates

Triphenylphosphine undergoes a smooth addition reaction with dialkyl acetylenedicarboxylates in the presence of isatin or 5-bromoisatin to produce stable crystalline phosphorus ylides. These products exist as a mixture of two geometrical isomers. Dynamic NMR effects have been observed in the (1)H NM...

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Bibliographic Details
Published inPolish journal of chemistry Vol. 79; no. 5; pp. 845 - 850
Main Authors Yavari, Dehghan, S, Alborzi, AR, Mohtat, B
Format Journal Article
LanguageEnglish
Published WARSAW Polish Chemical Soc 01.05.2005
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
triphenylphosphine
indole derivatives
isatin
intramolecular Wittig reaction
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Summary:Triphenylphosphine undergoes a smooth addition reaction with dialkyl acetylenedicarboxylates in the presence of isatin or 5-bromoisatin to produce stable crystalline phosphorus ylides. These products exist as a mixture of two geometrical isomers. Dynamic NMR effects have been observed in the (1)H NMR spectra of dimethyl 2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene)-succinate. These ylides are converted to dialkyl 2-(3-oxo-3H-indol-2-yl)-but-2-enedioates in boiling toluene.
ISSN:0137-5083