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

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

Volume: 12 Issue: 1

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

Affiliation:

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

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.

Cite this article as:

Krishnan Gokula Kannan, Sivakumar Rajamanickam and Thanikachalam Venugopal, Synthesis and Spectral Study of Some Novel Oxime Esters Derived from 3-azabicyclo[3.3.1]nonan-9-one Oxime, Letters in Organic Chemistry 2015; 12 (1) . https://dx.doi.org/10.2174/1570178611666141016215954