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Diels‐Alder ‐Reaktionen von 2′‐substituierten 3‐Vinyl‐1 H ‐indolen zu neuen anellierten Indol‐und Carbazol‐Derivaten
Author(s) -
Pfeuffer Ludwig,
Pindur Ulf
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700523
Subject(s) - chemistry , methyl acrylate , carbazole , adduct , cycloaddition , diels–alder reaction , michael reaction , methyl vinyl ketone , indole test , bicyclic molecule , acrylate , medicinal chemistry , catalysis , organic chemistry , copolymer , polymer
Diels‐alder Reactions of 2′‐Substituted 3‐Vinyl‐1 H ‐indoles to New Annellated Indole and Carbazole Derivatives New regio‐ and stereoselcctive cycloadditions between 2′‐ substituted 3‐vinyl‐l H ‐indoles and the dienophiles N ‐Phenylmaleimide, dimethyl acetylendicarboxylate, and methyl acrylate are reported. Products include some new carbazole derivatives and Michael adducts. In the presence of AlCl 3 as dicnophile‐activating catalyst, ‘ endo ’ preference for deriving cycloadducts is observed. In some cases, Michael addition competes with[4+2] cycloaddition.