Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions

Xiaobing Xu; Linfeng Liang; Jun Liu; Jingyu Yang; Lugen Mai; Yanzhong Li

doi:10.1016/j.tetlet.2008.10.080

Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions

Xiaobing Xu
, Linfeng Liang
, Jun Liu
, Jingyu Yang
, Lugen Mai
, Yanzhong Li^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

18 Scopus citations

Abstract

A convenient one-pot synthesis of 1,4-benzoxazines via three-component coupling and subsequent O-cyclization is reported. The present reaction provides an efficient protocol to functionalized 1,4-benzoxazine derivatives in good to high yields from aldehydes, amines and alkynes. Furthermore, the O-annulation process is completely regio- and stereoselective, only the six-membered rings and its Z-isomers were obtained.

Original language	English
Pages (from-to)	57-59
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2008.10.080
State	Published - 7 Jan 2009

Keywords

Benzoxazines
Copper catalyst
One-pot synthesis
Three-component couplings

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10.1016/j.tetlet.2008.10.080

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title = "Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions",

abstract = "A convenient one-pot synthesis of 1,4-benzoxazines via three-component coupling and subsequent O-cyclization is reported. The present reaction provides an efficient protocol to functionalized 1,4-benzoxazine derivatives in good to high yields from aldehydes, amines and alkynes. Furthermore, the O-annulation process is completely regio- and stereoselective, only the six-membered rings and its Z-isomers were obtained.",

keywords = "Benzoxazines, Copper catalyst, One-pot synthesis, Three-component couplings",

author = "Xiaobing Xu and Linfeng Liang and Jun Liu and Jingyu Yang and Lugen Mai and Yanzhong Li",

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T1 - Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions

AU - Xu, Xiaobing

AU - Liang, Linfeng

AU - Liu, Jun

AU - Yang, Jingyu

AU - Mai, Lugen

AU - Li, Yanzhong

PY - 2009/1/7

Y1 - 2009/1/7

N2 - A convenient one-pot synthesis of 1,4-benzoxazines via three-component coupling and subsequent O-cyclization is reported. The present reaction provides an efficient protocol to functionalized 1,4-benzoxazine derivatives in good to high yields from aldehydes, amines and alkynes. Furthermore, the O-annulation process is completely regio- and stereoselective, only the six-membered rings and its Z-isomers were obtained.

AB - A convenient one-pot synthesis of 1,4-benzoxazines via three-component coupling and subsequent O-cyclization is reported. The present reaction provides an efficient protocol to functionalized 1,4-benzoxazine derivatives in good to high yields from aldehydes, amines and alkynes. Furthermore, the O-annulation process is completely regio- and stereoselective, only the six-membered rings and its Z-isomers were obtained.

KW - Benzoxazines

KW - Copper catalyst

KW - One-pot synthesis

KW - Three-component couplings

UR - https://www.scopus.com/pages/publications/56949107723

U2 - 10.1016/j.tetlet.2008.10.080

DO - 10.1016/j.tetlet.2008.10.080

M3 - 文章

AN - SCOPUS:56949107723

SN - 0040-4039

VL - 50

SP - 57

EP - 59

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions

Abstract

Keywords

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