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Reactions of 3‐vinylindole derivatives with dienophiles
Author(s) -
MedioSimon Mercedes,
Pindur Ulf
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199119910162
Subject(s) - chemistry , adduct , yield (engineering) , carbazole , medicinal chemistry , organic chemistry , michael reaction , catalysis , materials science , metallurgy
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 .