Facile one-pot synthesis of 5-aryl/heterylidene-2-(2-hydroxyethyl- and 3-hydroxypropylamino)-thiazol-4-ones via catalytic aminolysis

作者：Golota Sergii; Sydorenko Ivan; Surma Roman; Karpenko Olexandr; Gzella Andrzej; Lesyk Roman^*

来源：Synthetic Communications, 2017, 47(11): 1071-1076.

DOI：10.1080/00397911.2017.1309669

• 2-Amino(imino)thiazol-4-ones
• 2-thioxothiazolidin-4-one/2-methylsulfanylthiazol-4-one
• amino alcohols
• catalytic aminolysis
• multicomponent reactions

A multicomponent synthetic approach for 5-aryl/heterylidene-2-(2hydroxyethylamino) -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 aminoimino tautomerism was observed for target 5-ylidene-2-alkylaminothiazol-4-ones.

• 出版日期2017