Issue 19, 1997
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Palladium-catalyzed chemoselective intramolecular cyclization of bromoanilinoalkenenitriles

Chau-Chen Yang,   Huo-Mu Tai  and  Pei-Jiun Sun  

Abstract

α-(o-Bromoanilino)alkenenitriles 1a–f and 2a–e and α-(N-alkenylamino)-β-(o-bromophenyl)propanenitrile 7a–c< and 8a–c undergo palladium-catalyzed conversion into o-(methylamino)benzonitrile 12, o-[(alkenylamino)ethenyl]benzonitriles 24a–c, N-alkenylanilines 26b, 26c, 3-benzazepines 29a, 29c, 31a and 32a, γ-carbolines 36 and pyrrolo[3,2-b]indole 45. The reactions involve intramolecular additions of arylpalladium to the cyano group and subsequent processes such as cyano group transposition, hydrolysis, electrocyclization, ethyl group transfer and oxidative aromatization. A general mechanism for the palladium-catalyzed arylation of a cyano group is proposed.

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Article information

DOI
https://doi.org/10.1039/A702710I
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 2843-2850

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Palladium-catalyzed chemoselective intramolecular cyclization of bromoanilinoalkenenitriles

C. Yang, H. Tai and P. Sun, J. Chem. Soc., Perkin Trans. 1, 1997, 2843 DOI: 10.1039/A702710I

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