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Synfacts 2009(7): 0724-0724  
DOI: 10.1055/s-0029-1217388
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Substituted Oxazoles

Contributor(s): Victor Snieckus, Toni Rantanen
Y.-m. Pan, F.-j. Zheng, H.-x. Ling, Z.-p. Zhan*
Xiamen University, P. R. of China
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

Reported is a one-pot PTSA-mediated version of the sequential propargylation-­cycloisomerization reaction to generate substituted oxazoles. Starting materials for this process are propargyl alcohols and primary amides. Solvent effects as well as catalytic amounts of various Lewis and equimolar amounts of some Brønsted acids were tested with one equivalent of PTSA being the catalyst and toluene the solvent of choice. Attempts to use catalytic amounts (50 mol%) of acid led to decreased yields (78% vs. 90%) and increased reaction times (24 h vs. 1 h). The substrate scope was well studied and the yields range from good to very good.