Transition-Metal-Free Heterocyclization of 1,3-Diynes with Nitriles in the Presence of Aqueous Potassium Hydroxide: Synthesis of 2,4-Disubstituted 5-[(E)-2-Phenylethenyl]-1,3-oxazoles

Ling Ming; Jialiang Tang; Xiaoming Zhao

doi:10.1055/s-0034-1378316

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(18): 2499-2505
DOI: 10.1055/s-0034-1378316

paper

Transition-Metal-Free Heterocyclization of 1,3-Diynes with Nitriles in the Presence of Aqueous Potassium Hydroxide: Synthesis of 2,4-Disubstituted 5-[(E)-2-Phenylethenyl]-1,3-oxazoles

Ling Ming

Department of Chemistry, State Key Laboratory of Pollution Control and Resource Reuse, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China Fax: +86(21)65981376 eMail: xmzhao08@mail.tongji.edu.cn

,

Jialiang Tang

Department of Chemistry, State Key Laboratory of Pollution Control and Resource Reuse, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China Fax: +86(21)65981376 eMail: xmzhao08@mail.tongji.edu.cn

,

Xiaoming Zhao*

Department of Chemistry, State Key Laboratory of Pollution Control and Resource Reuse, Tongji University, Siping Road 1239, Shanghai 200092, P. R. of China Fax: +86(21)65981376 eMail: xmzhao08@mail.tongji.edu.cn

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Abstract

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Abstract

A transition-metal-free heterocyclization of 1,3-diynes and nitriles in the presence of either aqueous potassium hydroxide or cesium hydroxide in 1,4-dioxane at 100 °C was realized. This method provided stereoselectively 2,4-disubstituted 5-[(E)-2-phenylethenyl]-1,3-oxazoles in moderate to good yields.

Key words

1,3-diyne - nitrile - heterocyclization - cesium hydroxide - potassium hydroxide

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