Convergent multicomponent assembly of 2-acyloxymethyl thiazoles

The Discovery of New Isocyanide‐Based Multicomponent Reactions

“…Thus we asked, is there nevertheless a way to use this interesting highly chemoselective Ugi reaction for a multicomponent thiazole synthesis? Several variants of this useful and novel MCR thiazole synthesis have since been reported, including complexity-oriented syntheses of thiazolo-b-lactams [18], in which two ring systems and five heavy atom bonds are newly formed (2 CaN, 2 CaS, 1 CaC), solid phase synthesis [19], and a Passerini variant of this reaction leading to 2-hydroxymethyl thiazoles [20]. Scheme 3.13 illustrates some of the possibilities [21].…”

A Facile Synthesis of 6,7-Fused Steroidal Thiazoles via 1,3-Intramolecular Migration of Bromine/Allylic Displacement of Bromine

“…10 Due to the significance of thiazole derivatives in medicinal chemistry, considerable effort has been devoted to develop alternate routes for their synthesis. [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Although several strategies with variable yields have been reported for the synthesis of steroidal as well as non-steroidal thiazoles, the Hantzsch's protocol [29][30][31] continues to be a method of choice involving the reaction of α-halocarbonyl compound with an appropriate thiourea or thioamide. Thus, we have also selected the Hantzsch's protocol for this purpose, 5-bromosteroidal ketones, [32][33] are selected instead of 7-bromosteroidal ketones because both lead to the same product but preparation of 7-bromocholestan-6-one [20][21] is much more tedious leading to a mixture of products.…”

Structural analysis of photo-degradation in thiazole-containing compounds by LC–MS/MS and NMR

“…This importance is reflected by the large number of marketed drugs containing the thiazole group, such as the anticonvulsant riluzole, the antiparkinsonian talipexole, the antibacterial sulfathiazole, the antiviral ritonavir [9], and the novel drug substances being developed as the large conductance calcium-activated potassium channel openers for overactive bladder indications [11]. In addition, the thiazole ring has also been widely used in the synthesis of natural products [12], polymers [13], fluorescent dyes [14], and insecticides [15]. Like other conjugated fivemembered heterocycles (such as furans, thiophenes, pyrroles, indoles, oxazoles, and imidazoles), thiazoles can undergo photo-oxygenation involving singlet oxygen ( 1 g ) under photoirradiation in solution [16] and in the solid state [17].…”