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
2012
Ramesh, Chintakunta | Lei, Po-Min | Janreddy, Donala | Kavala, Veerababurao | Kuo, Chun-Wei | Yao, Ching-Fa
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.
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