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

doi:10.1021/jo301313m

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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

22 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 language	English
Pages (from-to)	8451-8464
Number of pages	14
Journal	Journal of Organic Chemistry
Volume	77
Issue number	19
DOIs	https://doi.org/10.1021/jo301313m
Publication status	Published - 2012 Oct 5

ASJC Scopus subject areas

Organic Chemistry

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CCDC 883698: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkdj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkdj&sid=DataCite
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CCDC 883696: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkbg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkbg&sid=DataCite
Dataset
CCDC 883697: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkch, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkch&sid=DataCite
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Ramesh, C., Lei, P. M., Janreddy, D., Kavala, V., Kuo, C. W., & Yao, C. F. (2012). 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. Journal of Organic Chemistry, 77(19), 8451-8464. https://doi.org/10.1021/jo301313m

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. / Ramesh, Chintakunta; Lei, Po Min; Janreddy, Donala et al.
In: Journal of Organic Chemistry, Vol. 77, No. 19, 05.10.2012, p. 8451-8464.

Research output: Contribution to journal › Article › peer-review

Ramesh, C, Lei, PM, Janreddy, D, Kavala, V, Kuo, CW & Yao, CF 2012, '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', Journal of Organic Chemistry, vol. 77, no. 19, pp. 8451-8464. https://doi.org/10.1021/jo301313m

Ramesh C, Lei PM, Janreddy D, Kavala V, Kuo CW, Yao CF. 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. Journal of Organic Chemistry. 2012 Oct 5;77(19):8451-8464. doi: 10.1021/jo301313m

Ramesh, Chintakunta ; Lei, Po Min ; Janreddy, Donala et al. / 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. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 19. pp. 8451-8464.

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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.",

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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

Abstract

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CCDC 883698: Experimental Crystal Structure Determination

CCDC 883696: Experimental Crystal Structure Determination

CCDC 883697: Experimental Crystal Structure Determination

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