biostudies-literatureUnknown14(48)Aggarwal RThe present study reports some fascinating results of Hantzsch's [3 + 2] cyclic condensation of α-bromo-1,3-diketones, a tri-electrophilic synthon generated <i>in situ</i> by bromination of 1,3-diketones using the mild brominating reagent NBS with trinucleophilic <i>N</i>-substituted thioureas. Interestingly, out of a total of 20 combinations, 10 resulted in the exclusive formation of the desired 2-(<i>N</i>-arylamino)-5-acyl-4-methylthiazoles regioselectively, seven led to the formation of unexpected 2-(<i>N</i>-acylimino)-3-<i>N</i>-aryl-4-methylthiazoles through an interesting C-N acyl migration, and three furnished a mixture consisting of both products. The regioselectivity pattern of the two products may be attributed to a greater electrophilicity of the carbonyl carbon of the acetyl RSC advances35585-35600https://www.ebi.ac.uk/biostudies/studies/S-EPMC11544347biostudies-literatureReaction of unsymmetrical α-bromo-1,3-diketones with <i>N</i>-substituted thioureas: regioselective access to 2-(<i>N</i>-arylamino)-5-acyl-4-methylthiazoles and/or rearranged 2-(<i>N</i>-acylimino)-3-<i>N</i>-aryl-4-methylthiazoles.PMC11544347Sanz DAggarwal RSharma SJain NTorralba MCClaramunt RMDelgado PfalseReaction of unsymmetrical α-bromo-1,3-diketones with <i>N</i>-substituted thioureas: regioselective access to 2-(<i>N</i>-arylamino)-5-acyl-4-methylthiazoles and/or rearranged 2-(<i>N</i>-acylimino)-3-<i>N</i>-aryl-4-methylthiazoles.The present study reports some fascinating results of Hantzsch's [3 + 2] cyclic condensation of α-bromo-1,3-diketones, a tri-electrophilic synthon generated <i>in situ</i> by bromination of 1,3-diketones using the mild brominating reagent NBS with trinucleophilic <i>N</i>-substituted thioureas. Interestingly, out of a total of 20 combinations, 10 resulted in the exclusive formation of the desired 2-(<i>N</i>-arylamino)-5-acyl-4-methylthiazoles regioselectively, seven led to the formation of unexpected 2-(<i>N</i>-acylimino)-3-<i>N</i>-aryl-4-methylthiazoles through an interesting C-N acyl migration, and three furnished a mixture consisting of both products. The regioselectivity pattern of the two products may be attributed to a greater electrophilicity of the carbonyl carbon of the acetyl 2024-01-01T00:00:00Z2024 Nov2026-07-16T19:52:56.777Z2026-07-09T13:14:47.926ZS-EPMC115443473952408910.1039/d4ra05436a