Synthesis of some 3-(thiazol- 4-yl)-4-hydroxy coumarines

• Main Authors: Sukdolak Slobodan, Solujić-Sukdolak Slavica, Vuković Nenad, Manojlović Nedeljko, Krstić Ljubomir
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2004-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: hantzsch reaction; 3-(2-bromoacetyl)-4-hydroxychromen-2-one; 3-(thiazol-4-yl)-4-hydroxycoumarins
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390405319S.pdf

In this work, an easy and efficient procedure for the synthesis of eight 3-(thiazol-4-yl)-4-hydroxychromen-2-one derivatives is presented. 3-Acetyl-4-hydroxychromen- 2-one (1) was brominated with phenyltrimethylammonium tribromide to afford 3-(2-bromoacetyl)-4-hydroxychromen-2-one (2). Compound 2 reacts with thiourea, thioacetamide and ammonium dithiocarbamate to afford 3-(2-aminothiazol- 4-yl)-4-hydroxychromen-2-one (3) 4-hydroxy-3-(2-methylthiazol-4-yl)chromen- 2-one (4a) and 4-hydroxy-3-(2-mercaptothiazol-4-yl)chromen-2-one (5), respectively. In a similar manner, compound 2 was treated with four mono-N-substituted thioureas and thiobenzamide to give the corresponding 3-(thiazol-4-yl)-4-hydroxychromen- 2-one derivatives.