Solid support synthesis of 2,4-disubstituted thiazoles and aminothiazoles

✍ Scribed by Saı̈d El Kazzouli; Sabine Berteina-Raboin; Abderrahim Mouaddib; Gérald Guillaumet

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 244 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00471-9

✦ Synopsis

3-Iodobenzoic acid was loaded on Rink amide resin. Pd(0) coupling reaction with tributyl(1-ethoxyvinyl)tin followed by bromination using NBS gave an a-bromoketone bound to a solid support. Condensation of thioamide or thiourea, followed by TFA cleavage from the resin, gave 2,4-disubstituted thiazoles or 2-aminothiazoles, respectively. The primary amine of aminothiazole was treated with various acyl or sulfonyl chlorides to provide 2-substituted thiazole analogs.