• Journal of the Korean Chemical Society
• /
• v.47 no.6
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• pp.671-674
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• 2003

• Bulletin of the Korean Chemical Society
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• v.23 no.1
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• pp.19-20
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• 2002

• Bulletin of the Korean Chemical Society
• /
• v.21 no.9
• /
• pp.919-922
• /
• 2000

The cyclization reaction of N-(2-hydroxyethyl)-N'-phenylthioureas 2 containingambident nucleophile was ex-amined in the combination of a variety ofbases and p-toluenesulfonyl chloride (TsCl).N-(2-Hydroxyeth-yl) thioureas 2 were readily obtained in high yields from the reaction of the corresponding 1,2-aminoalcohols with phenyl isothiocyanate, avoiding the need for O-protection.The use of a one-pot reaction (NaOH/TsCl) was found to be most effective in producing the requisite 2-phenylaminothiazolines (S-cyclization) 3 in the case ofthioureas 2a-2e derived from N-unsubstituted aminoalcohols,while in the thioureas 2f and 2g prepared from N-substituted aminoalcohols the combination of Et3N and TsCl led to the S-cyclization products.