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Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)23H2O-Assisted Domino Sequence

Jungang Wang, Yan Cheng, Jiachen Xiang, Anxin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China, Email: chwuaxmail.ccnu.edu.cn

J. Wang, Y. Cheng, J. Xiang, A. Wu, Synlett, 2019, 30, 743-747.

DOI: 10.1055/s-0037-1612087 (free Supporting Information)



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Abstract

2,5-disubstituted oxazoles can be synthesized from easily available arylacetylenes and α-amino acids in the presence of Cu(NO3)23H2O and iodine. This reaction involves an I2/Cu(NO3)23H2O-assisted generation of α-iodo acetophenones, a Kornblum oxidation to phenylglyoxals, a condensation to imines, and a decarboxylation/annulation/oxidation reaction sequence.

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Key Words

oxazoles, α-amino acids, iodine, DMSO, copper catalysis, cascade reactions, alkynes


ID: J72-Y2019