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Synthesis of Indolylquinolines, Indolylacridines, and Indolylcyclopenta[b]quinolines from the Baylis–Hillman Adducts: An in Situ [1,3]-Sigmatropic Rearrangement of an Indole Nucleus To Access Indolylacridines and Indolylcyclopenta[b]quinolines

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journal contribution
posted on 05.10.2012 by Chintakunta Ramesh, Po-Min Lei, Donala Janreddy, Veerababurao Kavala, Chun-Wei Kuo, Ching-Fa Yao
A simple and easy route to the synthesis of a variety of structurally diverse indolylquinolines, indolylacridines, and indolylcyclopenta­[b]­quinoline derivatives via the reductive cyclization of C-alkylated indole derivatives, derived from acyclic as well as cyclic Baylis–Hillman adducts with indoles, is described. An unusual in situ [1,3]-sigmatropic rearrangement of the indole nucleus was observed during the reductive cyclicization of α-regioselective B–H adducts containing indoles to produce indolylacridines and indolylcyclopenta­[b]­quinoline derivatives.