A substituent-controlled general approach to access arylated pyran-2-ones and pyrano[3,4-c]pyran-1,8-diones |
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Authors: | Fateh V Singh Sumit Chaurasia Prakas R Maulik |
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Institution: | a Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow 226 001, India b Division of Molecular and Structural Biology, Central Drug Research Institute, Lucknow 226 001, India |
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Abstract: | 2H-Pyran-2-ones are useful precursors for the synthesis of various aromatic and heterocyclic compounds. In this Letter, we describe substituent-controlled direct access to functionalized 4-(2-oxo-1,2-diarylethyl)-5,6-diaryl-pyran-2-ones by stirring a mixture of 3-cyano-5,6-diaryl-2H-pyran-2-ones and functionalized deoxybenzoins through an unusual decyanation reaction. Under similar reaction conditions, the reactions of 3-carbomethoxy-5,6-diaryl-2H-pyran-2-ones with either substituted acetophenones or deoxybenzoins led to the synthesis of pyrano3,4-c]pyran-1,8-diones in excellent yields. |
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