Unanticipated Products from Reductive and Oxidative Cleavages of 1-Substituted 3,3-diphenyl-1 '-methylspiro [azetidine-2,3 '-indoline]-2 ',4-diones

[摘要]：Titled spiroazetidinones 1a,b undergo reductive cleavage on treatment with excess lithium aluminum hydride forming 3-benzhydryl-1-methylindole as the main product together with a gamma-amino alcohol depending upon the substituent present on the azetidin-2-one ring. Treatment of 1a with Ce(IV) ammonium nitrate affords 2-hydroxy-N-(4-methoxyphenyl)-2,2-diphenylacetamide besides the anticipated N-unsubstituted 2-azetidinone, whereas a similar treatment of 1-benzhydryl-3,3-diphenyl-2-azetidinone 1b affords the ring expansion product 1,3-oxazolidin-4-one. The products have been characterized on the basis of satisfactory analytical and spectral (IR, (1)H and (13)C-NMR, DEPT, HMBC) data and their formation is discussed.

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