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

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(NO 3 ) 2 •3H 2 O and iodine. This reaction ­process involves the I 2 /Cu(NO 3 ) 2 •3H 2 O-assisted transformation of ­arylacetylene...

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Bibliographic Details
Published in:Synlett 2019-04, Vol.30 (6), p.743-747
Main Authors: Wang, Jungang, Cheng, Yan, Xiang, Jiachen, Wu, Anxin
Format: Article
Language:English
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Summary: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(NO 3 ) 2 •3H 2 O and iodine. This reaction ­process involves the I 2 /Cu(NO 3 ) 2 •3H 2 O-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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1612087