Electrophilic substitution in indoles—II: The formation of 3,3-spirocyclic indole derivatives from tryptamines and their rearrangement to β-carbolines
摘要：
Attempts to isolate 3,3- spiro-cyclicindolenines thought to be intermediates in the cyclization of benzylidenetryptamines to tetrahydro-β-carbolines are described. One such spiro-pyrrolidinoindolenine, prepared by an alternative route from a spirocyclic oxindole derivative, was shown to undergo an extremely facile acid catalysed rearrangement to a tetrahydro-β-carboline. In contrast two piperidino iroindolenines did not rearrange to β-carbolines even under very vigorous acidic treatment. The relevance of these reactions to a new theory of electrophilic substitution in 3-substituted indoles, and the biogenesis of indole alkaloids is discussed.
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DOI：
10.1016/0040-4020(68)89038-6
被引量：
年份：
1968
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