The Diels-Alder reactions of quinone imine ketals: a versatile synthesis of highly substituted 5-methoxyindoles.
[reaction: see text]. N-benzoylated quinone imine ketals undergo smooth cycloadditions in a [4 + 2] sense to yield the expected cycloadducts. The crude cycloadducts, when subjected to a short series of simple transformations, produce synthetically useful quantities of 5-methoxyindoles in excellent overall yields.
Banfield
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SC
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
England
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DB
Kerr
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MA
D000447:Aldehydes / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D007097:Imines / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*
D000447:Aldehydes; D016227:Benzoquinones; D007097:Imines; D007211:Indoles; C004532:quinone