Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Ring Closure of N-(2-Hydroxyethyl)-N'-phenylthioureas:One-Pot Synthesis of 2-Phenylaminothiazolines

  • Published : 20000900
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Abstract

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.

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Cited by

  1. Investigation of the Cyclization of N-(2-Hydroxyethyl)-N'-phenylthioureas:Mitsunobu Conditions vs TsCl/NaOH System vol.23, pp.1, 2000, https://doi.org/10.5012/bkcs.2002.23.1.019
  2. Synthesis and spectroscopic analysis of substituted 2-aminothiazolines vol.1037, pp.None, 2000, https://doi.org/10.1016/j.molstruc.2012.12.031