Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

Pin Gao; Hong Xia Li; Xin Hua Hao; Dong Po Jin; Dao Qian Chen; Xiao Biao Yan; Xin Xing Wu; Xian Rong Song; Xue Yuan Liu; Yong Min Liang

doi:10.1021/ol503228x

Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

Pin Gao
, Hong Xia Li
, Xin Hua Hao
, Dong Po Jin
, Dao Qian Chen
, Xiao Biao Yan
, Xin Xing Wu
, Xian Rong Song
, Xue Yuan Liu
, Yong Min Liang

Lanzhou University

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

67 Scopus citations

Abstract

A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H₂O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

Original language	English
Pages (from-to)	6298-6301
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	24
DOIs	https://doi.org/10.1021/ol503228x
State	Published - 19 Dec 2014
Externally published	Yes

Access to Document

10.1021/ol503228x

Cite this

@article{e50ccc9a84b24441b02116167beff85b,

title = "Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation",

abstract = "A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.",

author = "Pin Gao and Li, \{Hong Xia\} and Hao, \{Xin Hua\} and Jin, \{Dong Po\} and Chen, \{Dao Qian\} and Yan, \{Xiao Biao\} and Wu, \{Xin Xing\} and Song, \{Xian Rong\} and Liu, \{Xue Yuan\} and Liang, \{Yong Min\}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = dec,

day = "19",

doi = "10.1021/ol503228x",

language = "英语",

volume = "16",

pages = "6298--6301",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

T1 - Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

AU - Gao, Pin

AU - Li, Hong Xia

AU - Hao, Xin Hua

AU - Jin, Dong Po

AU - Chen, Dao Qian

AU - Yan, Xiao Biao

AU - Wu, Xin Xing

AU - Song, Xian Rong

AU - Liu, Xue Yuan

AU - Liang, Yong Min

PY - 2014/12/19

Y1 - 2014/12/19

N2 - A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

AB - A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C=N bond and C=O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.

UR - https://www.scopus.com/pages/publications/84919621103

U2 - 10.1021/ol503228x

DO - 10.1021/ol503228x

M3 - 文章

AN - SCOPUS:84919621103

SN - 1523-7060

VL - 16

SP - 6298

EP - 6301

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C=N bond formation

Abstract

Access to Document

Other files and links

Fingerprint

Cite this