Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I2/Cu(NO3)2•3H2O-Assisted Domino Sequence

Jungang Wang; Yan Cheng; Jiachen Xiang; Anxin Wu

doi:10.1055/s-0037-1612087

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(06): 743-747
DOI: 10.1055/s-0037-1612087

letter

Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an I₂/Cu(NO₃)₂•3H₂O-Assisted Domino Sequence

Jungang Wang

^aSchool of Chemical Engineering, Guizhou Minzu University, Guiyang 550025, P. R. of China

,

Yan Cheng

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China eMail: chwuax@mail.ccnu.edu.cn

,

Jiachen Xiang

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China eMail: chwuax@mail.ccnu.edu.cn

,

Anxin Wu*

^bKey Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. of China eMail: chwuax@mail.ccnu.edu.cn

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Abstract

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Abstract

A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO₃)₂•3H₂O and iodine. This reaction process involves the I₂/Cu(NO₃)₂•3H₂O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.

Key words

oxazoles - α-amino acids - copper catalysis - cascade reactions - alkynes

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Referenzen

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26 General procedure for synthesis of 3 (3ac as an example) The mixture of phenylacetylene 1a (1.0 mmol), 2-amino-4-methylpentanoic 2c (1.0 mmol) was mixed with Cu(NO₃)₂•3H₂O (0.5 mmol), and I₂ (1.0 mmol). The mixture was heated at 60 °C in 4 mL of DMSO in a sealed vessel for 5 h till almost completed conversion of the substrates monitored by TLC analysis. Then 50 mL water was added to the mixture, which was extracted with EtOAc three times (3 × 50 mL). The extract was washed with Na₂S₂O₃ solution, dried over anhydrous Na₂SO₄ then the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc = 50/1) to afford the product 3ac” here

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