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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

23 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	8451-8464
頁數	14
期刊	Journal of Organic Chemistry
卷	77
發行號	19
DOIs	https://doi.org/10.1021/jo301313m
出版狀態	已發佈 - 2012 10月 5

ASJC Scopus subject areas

有機化學

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10.1021/jo301313m

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指紋

深入研究「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」主題。共同形成了獨特的指紋。

CCDC 883698: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P.-M. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkdj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkdj&sid=DataCite
資料集: Dataset
CCDC 883696: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P.-M. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkbg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkbg&sid=DataCite
資料集: Dataset
CCDC 883697: Experimental Crystal Structure Determination
Ramesh, C. (Creator), Lei, P.-M. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2013
DOI: 10.5517/ccynkch, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccynkch&sid=DataCite
資料集: Dataset

引用此

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 等.
於: Journal of Organic Chemistry, 卷 77, 編號 19, 05.10.2012, p. 8451-8464.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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, 卷 77, 編號 19, 頁 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 10月 5;77(19):8451-8464. doi: 10.1021/jo301313m

Ramesh, Chintakunta ; Lei, Po Min ; Janreddy, Donala 等. / 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. 於: Journal of Organic Chemistry. 2012 ; 卷 77, 編號 19. 頁 8451-8464.

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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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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

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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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JO - Journal of Organic Chemistry

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ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 883698: Experimental Crystal Structure Determination

CCDC 883696: Experimental Crystal Structure Determination

CCDC 883697: Experimental Crystal Structure Determination

引用此