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Regioselective Synthesis of Mono‐ and Dispiropyrazoline Derivatives via 1,3‐dipolar Cycloaddition with Nitrilimines

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The 1,3-dipolar cycloaddition reaction of (E,E)-1,3-bis(arylidene)indan-2-one with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides , affords predominantly monospiropyrazolines and as a mixture of diastereoisomers. Also dispiropyrazolines… Click to show full abstract

The 1,3-dipolar cycloaddition reaction of (E,E)-1,3-bis(arylidene)indan-2-one with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides , affords predominantly monospiropyrazolines and as a mixture of diastereoisomers. Also dispiropyrazolines are formed in moderate yields. The structure and stereochemistry of cycloadducts were confirmed by 1H and 13C-NMR spectroscopy, elemental analyses data, and single-crystal X-ray diffraction studies of and .

Keywords: cycloaddition; mono dispiropyrazoline; synthesis mono; dispiropyrazoline derivatives; regioselective synthesis; dipolar cycloaddition

Journal Title: Journal of Heterocyclic Chemistry
Year Published: 2017

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