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Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones via a sequential Ugi–Smiles type/nucleophilic substitution/cyclization reaction

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Abstract

A simple and innovative strategy is described for synthesizing a library of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-one backbones in mild conditions. This approach involves multiple bond-forming events in an Ugi–Smiles type reaction and the post-condensation of the Ugi–Smiles adduct incorporating a series of electron-withdrawing substituted benzaldehydes, primary amines, saccharin, and isocyanides followed by the addition of hydrazine hydrate for the post-condensation step.

Graphical abstract: Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones via a sequential Ugi–Smiles type/nucleophilic substitution/cyclization reaction

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Publication details

The article was received on 05 Aug 2018, accepted on 17 Sep 2018 and first published on 25 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03949F
Citation: New J. Chem., 2018, Advance Article
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    Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones via a sequential Ugi–Smiles type/nucleophilic substitution/cyclization reaction

    S. Ramezanpour, M. N. Rezaei, A. Vaezghaemi and F. Rominger, New J. Chem., 2018, Advance Article , DOI: 10.1039/C8NJ03949F

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