Preparation of 2-vinylindoline derivatives by oxidative cyclization of 2-alkenylanilines

Derivatives of 4,4 a ,9,9 a -tetrahydrocarbazole, 1,3 a ,4,8 b -tetrahydrocyclopenta[ b ]indoline, (2 R *,3 S *)-1-acetyl-3-methyl-2-vinylindoline, and also a mixture of (2 R *,3 S *)- and (2 R *,3 R *)-3-methyl-2-vinyl-indolines were obtained by refluxing N -acyl-2-(cycloalk-2-en-1-yl)- or N -acyl-...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2013-08, Vol.49 (5), p.689-697
Main Authors: Mazgarova, G. G., Skladchikov, D. A., Nikolaev, V. P., Gataullin, R. R.
Format: Article
Language:English
Subjects:
Acetates
Chemistry
Chemistry and Materials Science
Organic Chemistry
Palladium
Pharmacy
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Summary:Derivatives of 4,4 a ,9,9 a -tetrahydrocarbazole, 1,3 a ,4,8 b -tetrahydrocyclopenta[ b ]indoline, (2 R *,3 S *)-1-acetyl-3-methyl-2-vinylindoline, and also a mixture of (2 R *,3 S *)- and (2 R *,3 R *)-3-methyl-2-vinyl-indolines were obtained by refluxing N -acyl-2-(cycloalk-2-en-1-yl)- or N -acyl-2-(1-methylbut-2-en-1-yl)anilines with Pd(OAc) 2 in a toluene–pyridine mixture bubbled with air. From 2-(cyclopent-2-en-1-yl)-4-methylaniline under these conditions, 7-methyl-1,3 a ,4,8 b -tetrahydrocyclopenta[ b ]indole was formed. Its reaction with allyl bromide gave 4-allyl-7-methyl-1,3 a ,4,8 b -tetrahydrocyclopenta[ b ]indole in good yield.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-013-1299-9