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Synthesis 1996; 1996(2): 242-248
DOI: 10.1055/s-1996-4190
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Mononitroalkylations of Butane-2,3-dione

Giuliana Pitacco* , Alessandro Pizzioli, Ennio Valentin
  • *Dipartimento di Scienze Chimiche, Università di Trieste, Via L. Giorgieri 1, I-34127 Trieste, Italy, Fax +39(40)6763903; E-mail VALENNIO@UNIV.TRIESTE.IT
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Publication Date:
31 December 2000 (online)

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The morpholino enamine of monoprotected butane-2,3-dione reacts with cyclic and acyclic conjugated nitroalkenes in a Michael-type reaction to yield nitro-substituted α-diketones, after acidic hydrolysis of the mononitroalkylated enamine adducts. Cyclopentanone, hexahydro-1H-pentalen-2-one and octahydro-2H-inden-2-one derivatives are readily obtained by base-catalyzed intramolecular nitroaldol reaction of the acyclic hydrolysis products.

ketalized α-ketoenamines - nitroolefins - Stork reaction - 1,2-oxazine N-oxides - heptane-2,3,6-trione

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