Synthesis of 5-Phenylthiazolamines by Using Thiourea as an α-Bromination Shuttle

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• 作者：Irwan Iskandar Roslan ; Kian-Hong Ng ; Gaik-Khuan Chuah and Stephan Jaenicke
• 刊名：European Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 18, 2017
• 年：2017
• 卷：2017
• 期：3
• 页码：704-709
• 全文大小：1018K
• ISSN：1099-0690

文摘

A straightforward synthesis of 5-phenylthiazolamines by coupling thiourea with phenylacetones, phenylacetophenones, and β-tetralone has been developed. Thiourea acts as a substrate and an α-bromination shuttle by transferring a Br atom from CBrCl₃ to the α-carbon of the carbonyl moiety. A series of steps are then triggered to reach the final product. Isolated yields from 80 to 95 % were obtained. Key features of this protocol include its minimal use of reagents (i.e., substrates, CBrCl₃, and CsHCO₃), its short reaction times under mild conditions (at 80 °C for 2–3 h), and its ease of scale up to prepare gram quantities of product.