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Synthesis of 5‐Phenylthiazolamines by Using Thiourea as an α‐Bromination Shuttle
Author(s) -
Roslan Irwan Iskandar,
Ng KianHong,
Chuah GaikKhuan,
Jaenicke Stephan
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601410
Subject(s) - chemistry , thiourea , halogenation , moiety , reagent , substrate (aquarium) , combinatorial chemistry , coupling reaction , organic chemistry , catalysis , oceanography , geology
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 CBrCl 3 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, CBrCl 3 , and CsHCO 3 ), 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.