Atom-Economic Synthesis of Fully Substituted 2-Aminopyrroles via Gold-Catalyzed Formal [3+2] Cycloaddition between Ynamides and Isoxazoles

Xin-Yu Xiao; Ai-Hua Zhou; Chao Shu; Fei Pan; Ting Li; Long-Wu Ye

doi:10.1002/asia.201500447

Atom-Economic Synthesis of Fully Substituted 2-Aminopyrroles via Gold-Catalyzed Formal [3+2] Cycloaddition between Ynamides and Isoxazoles

Chem Asian J. 2015 Sep;10(9):1854-8. doi: 10.1002/asia.201500447. Epub 2015 Jul 14.

Authors

Xin-Yu Xiao¹, Ai-Hua Zhou¹, Chao Shu¹, Fei Pan¹, Ting Li¹, Long-Wu Ye^{2

3}

Affiliations

¹ State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, China.
² State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, China. longwuye@xmu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China. longwuye@xmu.edu.cn.

PMID: 26097238
DOI: 10.1002/asia.201500447

Abstract

A concise and flexible synthesis of fully substituted 2-aminopyrroles via gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles has been developed. Under mild reaction conditions, various 2-aminopyrrole derivatives were obtained in good to excellent yields, thus providing an efficient and atom-economic way for the construction of fully substituted 2-aminopyrroles.

Keywords: 2-aminopyrroles; cycloaddition; gold; homogeneous catalysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemical synthesis
Alkynes / chemistry*
Catalysis
Cycloaddition Reaction
Gold / chemistry*
Isoxazoles / chemical synthesis
Isoxazoles / chemistry*
Models, Molecular
Pyrroles / chemical synthesis*
Pyrroles / chemistry

Substances

Alkynes
Isoxazoles
Pyrroles
Gold