Thierry Masquelin

A new general three component solution-phase synthesis of 2-amino-1,3-thiazole and 2,4-diamino-1,3-thiazole combinatorial libraries

Abstract A general procedure for the solution-phase synthesis of amino-1,3-thiazole libraries 9 and 10 is described. Their preparation is based on the condensation of amidines 1 and thiouronium salts 2 with isothiocyanates 3 , affording amidino–thioureas and thioureido-thioureas of types 4 and 5 . Subsequent treatment with α-bromo ketones 6 led to the S -alkylated intermediate, which yielded 1,3-thiazoles of types 9 and 10 via a base-catalysed ring closure process ( Scheme 1 ) Download high-res image (102KB) Download full-size image Scheme 1 . . In addition, this methodology tolerates a diverse range of functionality without recourse to protection.

A novel access to 2,4-substituted quinolines from acetylenic ketones

Abstract 2, 4-Substituted quinolines of type 7 and 8 were synthesized starting from 2-amino thiophenol and acetylenic acetals 5 to yield various substituted benzo[b][1, 4] thiazepine intermediates of type 6 . Subsequent sulfur extrusion in refluxing toluene led to 2, 4-substituted quinoline acetals 7 , which were transformed into the corresponding 2-substituted quinoline-4-carbaldehydes 8 in good to excellent yields.