Abstract
A new strategy for solid-phase synthesis of 4,5-disubstituted 2,4-dihydro-3H-1,2,4-triazol-3-ones has been developed. The 4-substituted 5-(4-hydroxyphenyl)-1,2,4-triazol-3-one derivatives were synthesised from resin-bound acylhydrazines in several steps, in good overall yields and purity.
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