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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.

Autoren:   Ranjan, Pooja; Arora, Loveena; Prakash, Richa; K. Aneja, Deepak; Prakash, Om
Journal:   Letters in Organic Chemistry
DOI:   10.2174/1570178614666170321121411
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