Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 7, Pages 2924-2927Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702628g
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Reaction of asymmetrical 1,3-disubstituted thioureas with diacetoxyiodobenzene (DIB) produces regioselectively N-acetylurea in shorter time. Regioselectivity is dependent on the pK(a)'s of the amine attached to the thiourea moiety with acylation taking place toward the an-tine having a lower pK(a). This is the first example of DIB being employed as an N-acetylating agent. A mechanism for this novel transformation is also proposed. Mild reaction conditions, shorter reaction times, high efficiencies, environmentally benign methods, and facile isolation of the desired product make the present methodology a most suitable alternative.
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