Synthesis and Spectral Study of Some Novel Oxime Esters Derived from 3-azabicyclo[3.3.1]nonan-9-one Oxime

Author(s): Kannan Gokula Krishnan , Rajamanickam Sivakumar , Venugopal Thanikachalam .

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 1 , 2015

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Abstract:

Ten substituted 3-azabicyclo[3.3.1]nonan-9-one oxime ester derivatives 3-12 were synthesized from the starting material 3-azabicyclo[3.3.1]nonan-9-one oxime 2 with activated carboxylic acids in POCl3/pyridine. A wide range of carboxylic acids were used to produce the corresponding oxime esters up to 85% yield. The synthesized compounds were confirmed by FT-IR, NMR (1H, 13C and NOESY) and mass spectrometry. The chemical shift values were assigned unambiguously using one- and two-dimensional NMR spectroscopic data. The nuclear overhauser enhancement study suggests that the compounds exist in twin-chair conformation with equatorial orientation of the bulky substituents. The single crystal structure of compound 4 was determined to elucidate the structure unambiguously.

Keywords: Azabicyclo[3.3.1]nonane, carboxylic acid, Mannich reaction, NOESY, ring conformation.

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Article Details

VOLUME: 12
ISSUE: 1
Year: 2015
Page: [31 - 37]
Pages: 7
DOI: 10.2174/1570178611666141016215954

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