An Improved Synthetic Protocol and Plausible Mechanism in Forming Acetylpyridines from 2,6-Dicarbethoxypyridine

Author(s): Maliha Asma, Sheriff Adewuyi, Xiaofei Kuang, Amin Badshah, Wen-Hua Sun

Journal Name: Letters in Organic Chemistry

Volume 5 , Issue 4 , 2008

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2-Carbethoxy-6-acetylpyridine and 2,6-diacetylpyridine were transformed in good yields from the reaction of 2,6-dicarbethoxypyridine and EtOAc in the presence of sodium along with/without an equivalent of ethanol to sodium in toluene. The β-keto esters, the intermediates in the transformation of β-keto carboxylate into acetyl group, were isolated for understanding the plausible mechanism.

Keywords: 2-Carbethoxy-6-acetylpyridine, 2,6-diacetylpyridine, 2,6-dicarbethoxypyridine, Claisen Ester Condensation, anti-Claisen reaction

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Article Details

Year: 2008
Page: [296 - 299]
Pages: 4
DOI: 10.2174/157017808784049515
Price: $65

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