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IJC-B Vol.46B(04) [April 2007] >


Title: Synthesis and spectral studies of some heteroarylpiperidin-4-ones and their derivatives
Authors: Manimekalai, A
Jayabharathi, J
Porselvi, V M
Prabha, N
Keywords: NMR data
2,6-di-2'-furylpiperidin-4-one derivatives
Issue Date: Apr-2007
Publisher: CSIR
IPC CodeInt. Cl. ⁸ C07D
Abstract: The ¹H and ¹³C NMR spectra have been recorded for t(3)-methyl-r(2),c(6)-di-2'-furylpiperidin- 4-one 1, t(3)-ethyl-r(2),c(6)-di-2'-furylpiperidin-4-one 2, t(3)-isopropyl-r(2),c(6)-di-2'-furylpiperidin-4-one 3, t(3),t(5)-dimethyl-r(2),c(6)-di-2'-furylpiperidin-4-one 4 and their derivatives 5-12 and analysed. The ¹H-¹H COSY and ¹H-¹³C COSY spectra are recorded for t(3),t(5)-dimethyl-r(2),c(6)-di-2'-furylpiperidin-4-one oxime 8 and from the results boat conformation has been proposed for 8. The possible conformations of ethyl group at C-3 in 2, its oxime 6 and its hydrazone 12 have been suggested based on ¹³C spectral data. The spectral data predict that the azine 10 exists as a pair of diastereoisomers in solution. An attempt to synthesise t(3)-carboxyethyl-r(2),c(6)-di-2'-furylpiperidin-4-one 13 using ethyl acetoacetate as the ketone component has yielded an unexpected dihydropyridine namely 3,5-dicarboxyethyl-2,6-dimethyl-4-(2'-furyl)-1,4-dihydropyridine 14 (supported by spectral data) instead of the expected piperidin-4-one 13.
Page(s): 681-689
ISSN: 0376-4699
Source:IJC-B Vol.46B(04) [April 2007]

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