An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

Pankaj V. Khairnar; Tsai Hui Lung; Yi Jung Lin; Chi Yi Wu; Srinivasa Rao Koppolu; Athukuri Edukondalu; Praneeth Karanam; Wenwei Lin

doi:10.1021/acs.orglett.9b01395

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

Pankaj V. Khairnar
, Tsai Hui Lung
, Yi Jung Lin
, Chi Yi Wu
, Srinivasa Rao Koppolu
, Athukuri Edukondalu
, Praneeth Karanam
, Wenwei Lin^*

^*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

54 引文斯高帕斯（Scopus）

摘要

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.

原文	英語
頁（從 - 到）	4219-4223
頁數	5
期刊	Organic Letters
卷	21
發行號	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01395
出版狀態	已發佈 - 2019 6月 7

ASJC Scopus subject areas

生物化學
物理與理論化學
有機化學

存取文件

10.1021/acs.orglett.9b01395

其它文件與鏈接

Link to publication in Scopus

CCDC 1588092: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Lung, T.-H. (Contributor), Lin, Y.-J. (Contributor), Wu, C.-Y. (Contributor), Koppolu, S. R. (Contributor), Edukondalu, A. (Contributor), Karanam, P. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1q9jsb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q9jsb&sid=DataCite
資料集: Dataset
CCDC 1893512: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Lung, T.-H. (Contributor), Lin, Y.-J. (Contributor), Wu, C.-Y. (Contributor), Koppolu, S. R. (Contributor), Edukondalu, A. (Contributor), Karanam, P. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc21kc11, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21kc11&sid=DataCite
資料集: Dataset
CCDC 1588093: Experimental Crystal Structure Determination
Khairnar, P. V. (Contributor), Lung, T.-H. (Contributor), Lin, Y.-J. (Contributor), Wu, C.-Y. (Contributor), Koppolu, S. R. (Contributor), Edukondalu, A. (Contributor), Karanam, P. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1q9jtc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1q9jtc&sid=DataCite
資料集: Dataset

引用此

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title = "An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes",

abstract = "α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.",

author = "Khairnar, \{Pankaj V.\} and Lung, \{Tsai Hui\} and Lin, \{Yi Jung\} and Wu, \{Chi Yi\} and Koppolu, \{Srinivasa Rao\} and Athukuri Edukondalu and Praneeth Karanam and Wenwei Lin",

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doi = "10.1021/acs.orglett.9b01395",

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T2 - Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

AU - Khairnar, Pankaj V.

AU - Lung, Tsai Hui

AU - Lin, Yi Jung

AU - Wu, Chi Yi

AU - Koppolu, Srinivasa Rao

AU - Edukondalu, Athukuri

AU - Karanam, Praneeth

AU - Lin, Wenwei

PY - 2019/6/7

Y1 - 2019/6/7

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AB - α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.

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An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1588092: Experimental Crystal Structure Determination

CCDC 1893512: Experimental Crystal Structure Determination

CCDC 1588093: Experimental Crystal Structure Determination

引用此