Oxygen Atom Transfer as Key to Reverse Regioselectivity in the Gold(I)-Catalyzed Generation of Aminooxazoles from Ynamides

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Abstract

We report on gold(I)-catalyzed oxidative annulation involving ynamides, nitriles, and 2,3-dichloropyridine N-oxide. The application of 2,3-dichloropyridine N-oxide as an oxygen atom transfer reagent reverses the regioselectivity to give 5-amino-1,3-oxazoles, in comparison with the previously reported syntheses of aminooxazoles based on gold-catalyzed nitrene transfers to ynamides to furnish 4-amino-1,3-oxazoles. The developed oxygen atom transfer approach allows the generation of 1,3-oxazoles containing a variety of sulfonyl-protected alkylamino groups in the fifth position of the oxazole ring (29 examples; up to 88% yields). In addition, the use of N-substituted nitriles, namely cyanamides, leads to the facile generation of difficult-to-obtain 2,5-diaminooxazoles. The process is feasible for wide ranges of ynamides or nitriles, and it can be conducted in gram scale.

Original languageEnglish
Pages (from-to)1748-1757
Number of pages10
JournalJournal of Organic Chemistry
Volume86
Issue number2
DOIs
StatePublished - 15 Jan 2021

Scopus subject areas

  • Organic Chemistry

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