[4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes

[4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes

[4 + 2]-Cycloaddition reactions between 2-vinylindoles acting as hetero-dienes and β-acceptor substituted cyclic and acyclic enamines can be induced by formation of 2-vinylindole radical cations either via anodic oxidation or photoelectron transfer (PET) using catalytic amounts of triarylpyrylium te...

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Veröffentlicht in:Journal of organic chemistry 1996-06, Vol.61 (12), p.4136-4143
Hauptverfasser: Gürtler, Christoph F, Steckhan, Eberhard, Blechert, Siegfried
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container_end_page 4143
container_issue 12
container_start_page 4136
container_title Journal of organic chemistry
container_volume 61
creator Gürtler, Christoph F
Steckhan, Eberhard
Blechert, Siegfried
description [4 + 2]-Cycloaddition reactions between 2-vinylindoles acting as hetero-dienes and β-acceptor substituted cyclic and acyclic enamines can be induced by formation of 2-vinylindole radical cations either via anodic oxidation or photoelectron transfer (PET) using catalytic amounts of triarylpyrylium tetrafluoroborates as sensitizers. In this way, pyrido[1,2-a]indoles or indolo[1,2-a]hexahydro-1,8-naphthyridines are formed in one step with complete regio- and stereochemical control.
doi_str_mv 10.1021/jo951551o
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title [4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes
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