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New Reactions of 3‐Vinyl‐ and 3‐(2‐Propenyl)Indoles with N ‐Phenylmaleimide: [4 + 2] Cycloaddition, ene reaction, and dimerization
Author(s) -
Pfeuffer Ludwig,
Pindur Ulf
Publication year - 1988
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.19880710220
Subject(s) - chemistry , ene reaction , stereospecificity , cycloaddition , lewis acids and bases , propenyl , medicinal chemistry , catalysis , organic chemistry , stereochemistry
Depending on the substitution pattern of the aminobutadiene subunit in the selected 3‐vinylindoles 1, 3, 6 , and 9 , stereospecific [4 + 2] cycloadditions (‘ endo ’‐preference) and dimerizations take place on reaction with N ‐phenylmaleimide. In the reaction of 9 with N ‐phenylmaleimide in the absence of a Lewis ‐acid catalyst, a competing ene reaction occurs in addition to the Diels ‐ Alder reaction.