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|Title:||Synthesis of macrocycles derived from vanillin and isovanillin|
Mashraqui, Sabir H
|Abstract:||Readily available vanillin 1 and isovanillin 2 have been exploited for the first time to synthesise thia and aza-bridged macrocycles. Utilising a common approach, 1 and 2 are first converted into the corresponding key intermediates, dicholoro compounds 5 and 10. Cyclocondensations of these molecules with Na2S under high di lution provide thia-bridged macrocycles 6 and 11 and with p-toluenesulphonamide under basic condition, the aza- bridged macrocycles 7 and 12, respectively are obtained. The structures are fully supported by elemental analysis, mass and high resolution NMR data. Variable NMR measurements on 6 and 11 suggest that these macrocycles are conformationally mobile even at -55°C on the NMR time scale.|
|Appears in Collections:||IJC-B Vol.40B(01) [January 2001]|
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