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Untergehrer, Martin; Bracher, Franz (2020): A short divergent approach to highly substituted carbazoles and beta-carbolines via in situ-generated diketoindoles. In: Tetrahedron Letters, Vol. 61, No. 12, 151597
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Abstract

Based on an aza-alkylation/Michael addition cascade reaction developed by Kim and co-workers we have developed divergent cascade reactions leading to either highly substituted 1-hydroxycarbazoles, 3-hydroxycarbazoles or beta-carbolines, starting from readily accessible ortho-arylsulfonylaminobenzaldehydes. Olefination of the aldehyde functionality by aldol condensation or Wittig olefination gave reactive enone intermediates, which underwent the cascade reactions, either in two steps or in one-pot conversions, to give hydroxycarbazoles or complex beta-carbolines. (C) 2020 Elsevier Ltd. All rights reserved.