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Reactions of 3-vinylindole derivatives with dienophiles

✍ Scribed by Medio-Simon, Mercedes ;Pindur, Ulf

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
327 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Reactions of 3‐(1‐cyclohexenyl)‐1,2‐dimethylindole (1a) and the 1,2‐dihydrocarbazole 1b with some carbo‐ and heterodienophiles are described. Thus, compound 1a reacts to give ene, Michael‐type, and Diels‐Alder adducts, depending on the dienophile and reaction conditions. The 3‐vinylindole 1b reacts with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione or N‐phenylmaleimide in a dehydrogenative reaction to yield the fully aromatized carbazole 8.

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