Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Ming Chang P. Yeh; Cheng Wei Fang; Hsin Hui Lin

doi:10.1021/ol300434m

Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

Ming Chang P. Yeh^*
, Cheng Wei Fang
, Hsin Hui 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

27 引文斯高帕斯（Scopus）

摘要

A simple and efficient FeCl ₃-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl ₃.

原文	英語
頁（從 - 到）	1830-1833
頁數	4
期刊	Organic Letters
卷	14
發行號	7
DOIs	https://doi.org/10.1021/ol300434m
出版狀態	已發佈 - 2012 4月 6

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/ol300434m

其它文件與鏈接

CCDC 881091: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Fang, C.-W. (Creator) & Lin, H.-H. (Creator), Unknown Publisher, 2012
DOI: 10.5517/ccykv9m, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccykv9m&sid=DataCite
資料集: Dataset
CCDC 881090: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Fang, C.-W. (Creator) & Lin, H.-H. (Creator), Unknown Publisher, 2012
DOI: 10.5517/ccykv8l, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccykv8l&sid=DataCite
資料集: Dataset
CCDC 881089: Experimental Crystal Structure Determination
Yeh, M.-C. P. (Creator), Fang, C.-W. (Creator) & Lin, H.-H. (Creator), Unknown Publisher, 2012
DOI: 10.5517/ccykv7k, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccykv7k&sid=DataCite
資料集: Dataset

引用此

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title = "Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols",

abstract = "A simple and efficient FeCl 3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl 3.",

author = "Yeh, \{Ming Chang P.\} and Fang, \{Cheng Wei\} and Lin, \{Hsin Hui\}",

year = "2012",

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doi = "10.1021/ol300434m",

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volume = "14",

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journal = "Organic Letters",

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T1 - Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

AU - Yeh, Ming Chang P.

AU - Fang, Cheng Wei

AU - Lin, Hsin Hui

PY - 2012/4/6

Y1 - 2012/4/6

N2 - A simple and efficient FeCl 3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl 3.

AB - A simple and efficient FeCl 3-promoted cyclization/chlorination of cyclic tosylamine-tethered 8-aryl-2-en-7-yn-1-ols was observed. The reaction proceeded instantaneously at 23 °C in air to afford (Z)-4- (arylchloromethylene)-substituted azaspirocycles in good to excellent yields. This transformation can also be applied to the synthesis of spirocarbocyclic analogues from cyclic 8-aryl-2-en-7-yn-1-ols and FeCl 3.

UR - https://www.scopus.com/pages/publications/84859613811

UR - https://www.scopus.com/pages/publications/84859613811#tab=citedBy

U2 - 10.1021/ol300434m

DO - 10.1021/ol300434m

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AN - SCOPUS:84859613811

SN - 1523-7060

VL - 14

SP - 1830

EP - 1833

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Facile synthesis of azaspirocycles via iron trichloride-promoted cyclization/chlorination of cyclic 8-Aryl-5-aza-5-tosyl-2-en-7-yn-1-ols

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 881091: Experimental Crystal Structure Determination

CCDC 881090: Experimental Crystal Structure Determination

CCDC 881089: Experimental Crystal Structure Determination

引用此