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Facile one-pot synthesis of 5-aryl/heterylidene-2-(2-hydroxyethyl- and 3-hydroxypropylamino)-thiazol-4-ones via catalytic aminolysis |
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| Authors: | Sergii Golota Ivan Sydorenko Roman Surma Olexandr Karpenko Andrzej Gzella |
| Institution: | 1. Department of Pharmaceutical, Organic and Bioorganic Chemistry, Danylo Halytsky Lviv National Medical University, Lviv, Ukraine;2. Enamine Ltd, Kyiv, Ukraine;3. Department of Organic Chemistry, Poznan University of Medical Sciences, Poznan, Poland |
| Abstract: | A multicomponent synthetic approach for 5-aryl/heterylidene-2-(2-hydroxyethylamino)- and 2-(3-hydroxypropylamino)-thiazol-4-ones starting from 2-thioxothiazolidin-4-one or 2-methylsulfanylthiazol-4-one was developed. The proposed method involves simultaneous aminolysis of 2-thioxo- or 2-methylsulfanyl groups and Knoevenagel condensation with (hetero)aromatic aldehydes using 2-aminoethanol or 3-aminopropan-1-ol as catalysts. Side-chain prototropic amino–imino tautomerism was observed for target 5-ylidene-2-alkylaminothiazol-4-ones. |
| Keywords: | 2-Amino(imino)thiazol-4-ones 2-thioxothiazolidin-4-one/2-methylsulfanylthiazol-4-one amino alcohols catalytic aminolysis multicomponent reactions |