The synthesis of substituted 2‐aminothiazoles

Abstract

The preparation of 4‐ and 5‐acyl‐ and aroyl‐2‐substituted aminothiazoles is described. The condensation of thioureas with acyl halides leading to 4,5‐disubstituted‐2‐aminothiazoles and 7‐(4H)benzothiazolones is discussed. A discussion of the isolation of various intermediates and the mechanistic pathway is also included. A number of 2‐anilino or 2‐benzyl‐4‐ or 5‐aroylthiazoles possessed moderate oral antitubercolosis activity (2).

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

“…The Hantzsch thiazole synthesis using the condensation of α-haloketones with thioureas [ 290 , 291 , 292 , 293 , 294 , 295 , 296 , 297 , 298 , 299 , 300 , 301 , 302 , 303 , 304 , 305 ] or thioamides [ 306 , 307 , 308 , 309 , 310 , 311 , 312 , 313 , 314 , 315 , 316 , 317 , 318 , 319 , 320 , 321 ] 129 was es-tablished a century ago [ 290 , 291 ]. It is well-known that during Hantzsch thiazole synthesis an intermediate 130a and/or a cyclic hydroxy isomer 130b is formed ( Scheme 36 ).…”

The Chemistry of α‐Haloketones and Their Utility in Heterocyclic Synthesis

“…The Hantzsch thiazole synthesis using the condensation of α-haloketones with thioureas [290][291][292][293][294][295][296][297][298][299][300][301][302][303][304][305] or thioamides [306][307][308][309][310][311][312][313][314][315][316][317][318][319][320][321] 129 was established a century ago [290,291]. It is well-known that during Hantzsch thiazole synthesis an intermediate 130a and/or a cyclic hydroxy isomer 130b is formed (Scheme 36).…”