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Novel [3+2] radical annulations of cyano-substituted aryl radicals with alkynes

✍ Scribed by Rino Leardini; Daniele Nanni; Antonio Tundo; Giuseppe Zanardi

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
200 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

New radical annulation reactions are described involving addition of orrho-cyano-substituted aryl radicals to alkynes. Addition of the aryl radical to the C-C triple bond gives rise to a vinyl radical, whose cyclisation onto the carbon atom of the nitrile moiety produces an iminyl radical. The final reaction products derive from the iminyl by hydrogen abstraction -followed by hydrolysis -, dimerisation, or cyclisation onto another aromatic ring. In the last case, new nitrogen heterocycles are formed through a novel application of the radical addition, tandem cyclisation strategy.

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