The Chemistry of α,β-Ditosyloxy Ketones: Hypervalent Iodine (III) Mediated Synthesis of Alkynes from α,β-Unsaturated Carbonyl Compounds Containing Pyrazole Moiety

Title:The Chemistry of α,β-Ditosyloxy Ketones: Hypervalent Iodine (III) Mediated Synthesis of Alkynes from α,β-Unsaturated Carbonyl Compounds Containing Pyrazole Moiety

Volume: 14 Issue: 4

Author(s): Pooja Ranjan, Loveena Arora, Richa Prakash, Deepak K. Aneja*Om Prakash*

Affiliation:

• Department of Chemistry, Faculty of Science, Chaudhary Bansi Lal University, P.O. Box: 127021, Bhiwani,India

• Department of Chemistry, Faculty of Science, Kurukshetra University, Kurukshetra, P.O. Box: 136119,India

Keywords: Alkynes, α, β-chalcone ditosylates, α, β-chalcone dibromides, desoxybenzoin, [hydroxy(tosyloxy)iodo]benzene.

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.

Cite this article as:

Ranjan Pooja , Arora Loveena , Prakash Richa , Aneja K. Deepak *, Prakash Om *, The Chemistry of α,β-Ditosyloxy Ketones: Hypervalent Iodine (III) Mediated Synthesis of Alkynes from α,β-Unsaturated Carbonyl Compounds Containing Pyrazole Moiety, Letters in Organic Chemistry 2017; 14 (4) . https://dx.doi.org/10.2174/1570178614666170321121411

DOI https://dx.doi.org/10.2174/1570178614666170321121411	Print ISSN 1570-1786
Publisher Name Bentham Science Publisher	Online ISSN 1875-6255