Synthesis of γ-N-acylamino-β-keto esters and ethyl 5-oxazoleacetates via Ritter reaction and hydration of γ-hydroxy-α,β-alkynoic esters

Rao, K. Srinivasa ; Reddy, D. Srinivasa ; Pal, Manojit ; Mukkanti, K. ; Iqbal, Javed (2006) Synthesis of γ-N-acylamino-β-keto esters and ethyl 5-oxazoleacetates via Ritter reaction and hydration of γ-hydroxy-α,β-alkynoic esters Tetrahedron Letters, 47 (26). pp. 4385-4388. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2006.04.092

Related URL: http://dx.doi.org/10.1016/j.tetlet.2006.04.092

Abstract

The classical Ritter reaction on γ-hydroxy-α,β-alkynoic esters produced γ-N-acylamino-β-keto esters or ethyl 5-oxazoleacetates using alkyl or aryl nitriles, respectively. The γ-N-acylamino-β-keto esters resulting from alkyl nitriles are useful intermediates in the synthesis of a variety of building blocks. We also show that these can be converted into ethyl 5-oxazoleacetates using an additional step involving POCl3.

Item Type:Article
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