Journal of Organic Chemistry 2003-07-25

One-pot route to new alpha,alpha-difluoroamides and alpha-ketoamides.

Rajendra P Singh, Jean'ne M Shreeve

文献索引：J. Org. Chem. 68 , 6063, (2003)

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摘要

New alpha,alpha-difluoroamides (4a-d, 6a-d) and alpha-ketoamides (5a-d, 7a-d) result from one-pot reactions of alpha-ketoacids, RCOCO(2)H (R = C(6)H(5), CH(3), CH(3)CH(2), thienyl) (1a-d) with bis(2-methoxyethyl)aminosulfur trifluoride [(CH(3)OCH(2)CH(2))(2)NSF(3)] (2) (Deoxofluor) or diethylaminosulfur trifluoride [(CH(3)CH(2))(2)NSF(3))] (3) (DAST). Product yields depend on reaction times and the ratio of reagents used. Longer reaction times ( approximately 36 h) with a 1:2 ratio of alpha-ketoacids and 2 or 3 gave major yields of the alpha,alpha-difluoroamides, and shorter reaction times ( approximately l h) produced alpha-ketoamides as the major products. Reactants in a 1:1 ratio resulted in alpha-ketoamides only.