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(4 + 3) Cycloaddition Reaction of Sulfonylphthalide with N,N'-Cyclic Azomethine Imines: Synthesis of Pyrimidinone-Fused Naphthoquinones.

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A base-mediated [4 + 3] cycloaddition reaction of sulfonylphthalide with N,N'-cyclic azomethine imines to facilely synthesize novel pyrimidinone-fused naphthoquinones is described. The prepared compounds can be readily converted to isoquinoline-1,4-dione… Click to show full abstract

A base-mediated [4 + 3] cycloaddition reaction of sulfonylphthalide with N,N'-cyclic azomethine imines to facilely synthesize novel pyrimidinone-fused naphthoquinones is described. The prepared compounds can be readily converted to isoquinoline-1,4-dione derivatives via alkaline methanolysis. Alternatively, the isoquinoline-1,4-dione can also be prepared by base-mediated one-pot three-component reaction of sulfonylphthalide with N,N'-cyclic azomethine imines in methanol.

Keywords: cyclic azomethine; reaction sulfonylphthalide; sulfonylphthalide cyclic; azomethine imines

Journal Title: Organic letters
Year Published: 2023

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