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1 Polish Journal of Chemistry

1 2004

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Synthesis of 2-Oxa-4,6,8-triazabicyclo[3.3.0]octanes

Kakanejadifard A., Kargar K., Farnia M., Bahrami Ziabari M., Todaro L.

Polish Journal of Chemistry

2004

Vol. 78 / nr 1

45-51

4,6,8-Triaryl-2-oxa-4,6,8-triazabicyclo[3.3.0]octanes (4) and 6,8-diaryl-2,4-dioxa-6,8- diazabicyclo[3.3.0]octanes (5) were synthesized by condensation of arylamines with glyoxal and formaldehyde in CH3CN. Change of the reaction solvent to CH3OH leads to dimethoxy imidazolidine (7). Depending on the reaction conditions, intermediates with different configuration are formed. The X-ray crystal structure determination of 5 shows a cis fusion of the two five-membered rings, in line with two anomeric effect; a strong nN_óC-O * interaction and a weak nO_óC-N * . The compound5 is a rare molecule containing N-C-N and O-C-O units adjacent to N-C-O anomeric moiety. The results show, that in the presence of anomeric unit of N-C-O, the anomeric effect of N-C-N and O-C-O moieties are negligible.