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Synfacts 2005(3): 0359-0359  
DOI: 10.1055/s-2005-921617
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Alkylamino-4,5-disubstituted-1,2,4-triazoles on PEG6000

Contributor(s): Yasuhiro Uozumi, Ray Kawade
Y.-X. Zong, J.-K. Wang, G.-R. Yue, L. Feng, Z.-E. Song, H. Song, Y.-Q. Han
Hexi University, Zhangye, P. R. of China
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Publikationsdatum:
22. November 2005 (online)

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Significance

3-Arylamino-4,5-disubstituted-1,2,4-triazoles 4 were prepared via several steps starting from amines 1 anchored on the 3-methoxy-4-formylphenyl poly(ethylene glycol) (soluble polymer). Thus, amines 1 reacted with several isothiocyanates to give the corresponding thioureas 2. The reaction of thioureas 2 with arylacryl hydrazides followed by treatment with Hg(OAc)2 gave the desired triazoles 3, bound to a soluble polymer, with high purity. 4-Benzyl-1,2,4-triazoles 4a-c (3 varieties, 56-96% yield), and 4-butyl-1,2,4-triazoles 4d-f (3 varieties, 77-81% yield), were readily isolated via TFA-mediated cleavage from the corresponding PEG-supported triazoles 3 in high yields with high purity.