Tributyltin hydride-mediated cyclisations of cinnamic enamides to piperidin-2-ones or pyrrolidin-2-ones. Indolizidinone ring formation by tandem radical cyclisation

Efficient 6- endo- trig free radical cyclisations of various 3-phenyl-acryl enamides to piperidin-2-ones, by using Bu 3SnH and AIBN in boiling toluene, are reported. A different result has been observed for related enamide system without phenyl substituent at the 3-position of an acrylic moiety, as...

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Bibliographic Details
Published in:Tetrahedron 2004-09, Vol.60 (37), p.8181-8188
Main Authors: Flisińska-Łuczak, Joanna, Leśniak, Stanisław, Nazarski, Ryszard B.
Format: Article
Language:English
Subjects:
Enamides
Indolizine
Lactams
Tandem radical cyclisation
Tributyltin hydride
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Summary:Efficient 6- endo- trig free radical cyclisations of various 3-phenyl-acryl enamides to piperidin-2-ones, by using Bu 3SnH and AIBN in boiling toluene, are reported. A different result has been observed for related enamide system without phenyl substituent at the 3-position of an acrylic moiety, as such a reaction of 3-methyl-butenoic acid cyclohex-1-enyl-methyl-amide afforded only the 5- exo- trig product. The difference in the cyclisation mode has been explained in terms of a reversible process leading to the thermodynamically more stable product. An application of this method for the tandem cyclisation permits to obtain idolizidine derivatives. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.06.095