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

Department of Chemistry

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

24 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1830-1833
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol300434m
Publication status	Published - 2012 Apr 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol300434m

Cite this

@article{be233607873e4ef3ae2fb380b5a91a35,

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",

month = apr,

day = "6",

doi = "10.1021/ol300434m",

language = "English",

volume = "14",

pages = "1830--1833",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=84859613811&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84859613811&partnerID=8YFLogxK

U2 - 10.1021/ol300434m

DO - 10.1021/ol300434m

M3 - Article

C2 - 22455465

AN - SCOPUS:84859613811

VL - 14

SP - 1830

EP - 1833

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this