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- Title
Synthesis of 5-Phenylthiazolamines by Using Thiourea as an α-Bromination Shuttle.
- Authors
Roslan, Irwan Iskandar; Ng, Kian‐Hong; Chuah, Gaik‐Khuan; Jaenicke, Stephan
- Abstract
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.
- Subjects
CHEMICAL synthesis; PHENYL compounds; RING formation (Chemistry); HALOGENATION; SULFUR
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 3, p704
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601410