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Synthesis 2003(10): 1569-1573
DOI: 10.1055/s-2003-40511
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© Georg Thieme Verlag Stuttgart ˙ New York

Poly(ethylene glycol) Supported Liquid-Phase Synthesis of 1,2,4-Oxadiazolines

Xu-Feng Lin, Jian Zhang, Sun-Liang Cui, Yan-Guang Wang*
Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China
Fax: +86(571)87951512; e-Mail: orgwyg@css.zju.edu.cn;
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Publication History

Received 24 March 2003
Publication Date:
08 July 2003 (online)

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Abstract

The liquid-phase synthesis of oxadiazolines via 1,3-dipolar cycloaddition reaction on poly(ethylene glycol) support (PEG) is described. 1,3-Dipolar cycloadditions of nitrile oxide generated in situ on soluble polymer with a variety of imines provided a library of 1,2,4-oxadiazolines in good yields and purity. The reactions were run in the homogeneous phase and the synthetic sequen­ces were performed in parallel one-pot fashion. Quantitative conversion in the 1,3-dipolar cycloaddition reaction was verified by 1H NMR analysis. The polymer bound products were isolated in excellent yields by simple precipitation of the soluble support.

Key words

1,3-dipolar cycloaddition - soluble polymer - liquid-phase synthesis - oxadiazolines - poly(ethylene glycol)