The Chemistry of α,β-Ditosyloxy Ketones: Hypervalent Iodine (III) Mediated Synthesis of Alkynes from α,β-Unsaturated Carbonyl Compounds Containing Pyrazole Moiety
Abstract:
Background: The present study is an effort to extend the utility of the α,β-ditosyloxy chalcone derivatives in establishing the reaction patterns of these compounds which at once was thought that they might behave similar to α,β-dibromo ketones but the results
obtained were quite different and interesting in nature. Methods: In the present methodology, the α,β-chalcone ditosylates containing pyrazoles were prepared from corresponding chalcone derivatives on treatment with [hydroxyl(tosyloxy)iodo]benzene in dichloromethane at room
temperature and that were further allowed to react with potassium hydroxide in methanol. Results: A new series of acetylenic ketones were obtained in the present case in excellent yield. The analytical data of the compounds fully satisfy the structures of the compounds. Conclusions:
In the present case, the α,β-chalcone ditosylates lead to the elimination of ditosyloxy groups and the products isolated are acetylenic ketones which are stable under the reaction conditions. Hence, it offers a facile and convenient route for the synthesis of acetylenic ketones
which are difficult to synthesize otherwise.
Authors:
Ranjan, Pooja; Arora, Loveena; Prakash, Richa; K. Aneja, Deepak; Prakash, Om
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