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An Effective Nitrilimine Cycloaddition for the Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazoles from Oximes with Hydrazonoyl Hydrochlorides

Li-Ya Wang, Wen-Che Tseng, Hui-Yi Lin, Fung Fuh Wong*

*Graduate Institute of Pharmaceutical Chemistry, China Medical University, No. Hsueh 91, Shih Rd., Taichung, Taiwan 40402, R. O. C., Email: wongfungfuhyahoo.com.tw

L.-Y. Wang, W.-C. Tseng, H.-Y. Lin, F. F. Wong, Synlett, 2011, 1467-1471.

DOI: 10.1055/s-0030-1260759


Abstract

An effective 1,3-dipolar cycloaddition for the synthesis of 1,3,5-trisubstituted 1,2,4-triazole derivatives by reaction of oximes with hydrazonoyl hydrochlorides using triethylamine as a base gave the desired 1,3,5-trisubstituted 1,2,4-triazoles in good yields. The reaction was applicable to aliphatic, cyclic aliphatic, aromatic and heterocyclic oxime substrates.


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Key Words

1,2,4-triazoles, hydrazonoyl hydrochlorides, nitrilimines, 1,3-dipolar cycloaddition, oximes


ID: J60-Y2011-1810