Synthesis 2014; 46(18): 2499-2505
DOI: 10.1055/s-0034-1378316
paper
© Georg Thieme Verlag Stuttgart · New York

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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Received: 17. März 2014

Accepted after revision: 20. Mai 2014

Publikationsdatum:
24. Juni 2014 (online)


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.

Supporting Information