Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement

Synthesis of 6-Alkyl Analogues of the 1-Azabicyclo[4.3.0]nonan-2-one System by a Strategy of Geminal Acylation and Beckmann Rearrangement.-As result of several exploratory reactions a route to title compounds (V) and (XIII) is presented involving three key steps: formation of the cyclopentadione ring by geminal acylation of ketone (I) or acetal (VIII) with cyclobutenes (II) or (IX), ring expansion of the cyclopentadione moiety of derivatives (III) and (XI) to keto lactams (IV) and (XII) by Beckmann rearrangement, and the cyclization of the amidic nitrogen onto the terminal double bond of the lactams to give diastereomeric mixtures of the target compounds. The iodine of product (V) is replaced by a hydroxy group via the corresponding propionate to give hydroxymethyl derivative (VII) in quantitative yield.-(ELLIOTT, CHRISTINE E.; MILLER, DAVID O.; BURNELL, D. JEAN; J. Chem. Soc., Perkin Trans. 1 (2002) 2, 217-226; Dep. Chem., Memorial Univ., St. John's, Newfoundland A1B 3X7, Can.; EN)

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ChemInform Abstract: Synthesis of 6‐Alkyl Analogues of the 1‐Azabicyclo[4.3.0]nonan‐2‐one System by a Strategy of Geminal Acylation and Beckmann Rearrangement.

Elliott

Miller

Burnell

2002

ChemInform

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Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement

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ChemInform Abstract: Synthesis of 6‐Alkyl Analogues of the 1‐Azabicyclo[4.3.0]nonan‐2‐one System by a Strategy of Geminal Acylation and Beckmann Rearrangement.

ChemInform Abstract: Synthesis of 6‐Alkyl Analogues of the 1‐Azabicyclo[4.3.0]nonan‐2‐one System by a Strategy of Geminal Acylation and Beckmann Rearrangement.

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