Solution-phase Synthesis of a Combinatorial Library of 3-[4-(Coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid Amides

• Main Authors: V. Chernykh, S. Vlasov, S. Kovalenko, I. Zhuravel
• Format: Article
• Language: English
• Published: MDPI AG 2005-02-01
• Series: Molecules
• Subjects: Coumarin derivatives; 2-aminothiazole derivatives; dicarboxylic acids; combinatorial synthesis.
• Online Access: http://www.mdpi.com/1420-3049/10/2/444/

The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks – 3- [4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 – by the reaction of 3-(É-bromacetyl)coumarins 1 with 3-amino(thioxo)methylcarbamoylpropanoic acid (5); 2) the synthesis of the corresponding 3-[4-(coumarin-3-yl)-1,3-thiazol-2-yl- carbamoyl]propanoic acids amides 9 using 1,1’-carbonyldimidazole as a coupling reagent. The advantages of the method compared to existing ones are discussed.