Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines†
Alexander V.
Aksenov, 
*a
Dmitrii A.
Aksenov,
a
Georgii D.
Griaznov,
ab
Nicolai A.
Aksenov,
a
Leonid G.
Voskressensky
c
and
Michael
Rubin
*ab
*a
Dmitrii A.
Aksenov,
a
Georgii D.
Griaznov,
ab
Nicolai A.
Aksenov,
a
Leonid G.
Voskressensky
c
and
Michael
Rubin
*ab
Abstract
The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered.
![Graphical abstract: Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines](/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=C8OB00588E&imageInfo.ImageIdentifier.Year=2018)
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