Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement

Lithiation of 2-bromo-4-(1,3-dioxolan-2-yl)-1,3-thiazole

“…For the introduction of an aldehyde group, morpholin-4-carbaldehyde was used, and N-methoxy-N-methylacetamide was used to introduce an acetyl group, which led to 2-bromo-4-(1,3-dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde 4 ( [21][22][23] To confirm the structure of compounds (2-6) and to study a possibility of the Halogen Dance Reaction, we performed lithiation of 1,3-thiazole 1 in the above conditions using water as the electrophile. As a result, we obtained the starting compound 1 with a quantitative yield.…”

Polyarylated Thiazoles via a Combined Halogen Dance – Cross‐Coupling Strategy

“…Both, the Stille [19][20][21] [Pd(PPh 3 ) 4 , CsF, toluene] and Suzuki-Miyaura [22] protocols [Pd(PPh 3 ) 4 , NaHCO 3 , DME, H 2 O] gave the same result (product 9 in 60 % and 61 %, respectively). Additionally, we also investigated the effect of different substituents on the benzene ring on the outcome of Suzuki-Miyaura cross-coupling reactions.…”

A Rapid, Four-Component Synthesis of Functionalized Thiazoles

“…Thus the thiazole nucleus has been much studied in the field of organic and medicinal chemistry [6]. Several methods for the synthesis of thiazole derivatives have been developed [7][8][9][10][11], the most widely used method *Address correspondence to this author at the Chemistry Department, Faculty of Sciences, Shahid Rajaee Teacher Training University, P.O. Box 16785-163, Tehran, Iran; Tel: +98-21-22970003; Fax: +98-21-22970033; E-mail: sabbaghan@srttu.edu, msaba16us@yahoo.com being the Hantzsch's synthesis, in which an -halocarbonyl compound is condensed with a thioamides, thioureas, thiocarbamic acids, or dithiocarbamic acids [12][13][14].…”