Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles

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Abstract

Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-1 are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylation of acetylacetone and benzoylacetone affords β-diketones 10a-d and 13a-c, respectively.

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Katritzky, A. R., Wang, Z., Wang, M., Wilkerson, C. R., Hall, C. D., & Akhmedov, N. G. (2004). Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles. Journal of Organic Chemistry, 69(20), 6617–6622. https://doi.org/10.1021/jo049274l

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