A substituent-controlled general approach to access arylated pyran-2-ones and pyrano[3,4-c]pyran-1,8-diones

Singh, Fateh V. ; Dixit, Manish ; Chaurasia, Sumit ; Raghunandan, Resmi ; Maulik, Prakas R. ; Goel, Atul (2007) A substituent-controlled general approach to access arylated pyran-2-ones and pyrano[3,4-c]pyran-1,8-diones Tetrahedron Letters, 48 (51). pp. 8998-9002. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2007.10.095

Related URL: http://dx.doi.org/10.1016/j.tetlet.2007.10.095

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 pyrano[3,4-c]pyran-1,8-diones in excellent yields.

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