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

…, Z Wang, M Wang, CR Wilkerson, CD Hall…

Index: Katritzky, Alan R.; Wang, Zuoquan; Wang, Mingyi; Wilkerson, Chavon R.; Hall, C. Dennis; Akhmedov, Novruz G. Journal of Organic Chemistry, 2004 , vol. 69, # 20 p. 6617 - 6622

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Citation Number: 82

Abstract

Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-l 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.

~16%

~96%

~82%

~84%

~56%

~76%

~63%

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