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

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

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19 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)8451-8464
Number of pages14
JournalJournal of Organic Chemistry
Volume77
Issue number19
DOIs
Publication statusPublished - 2012 Oct 5

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Quinolines
Indoles
Derivatives
Cyclization
indole
quinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
abstract = "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.",
author = "Chintakunta Ramesh and Lei, {Po Min} and Donala Janreddy and Veerababurao Kavala and Kuo, {Chun Wei} and Yao, {Ching Fa}",
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T1 - Synthesis of indolylquinolines, indolylacridines, and indolylcyclopenta[b] quinolines from the Baylis-Hillman adducts

T2 - An in situ [1,3]-sigmatropic rearrangement of an indole nucleus to access indolylacridines and indolylcyclopenta[b]quinolines

AU - Ramesh, Chintakunta

AU - Lei, Po Min

AU - Janreddy, Donala

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

PY - 2012/10/5

Y1 - 2012/10/5

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AB - 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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