Azetidin-2-ones: structures of anti-mitotic compounds based on the 1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one core.

A series of related substituted 1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-ones have been characterized: 3-(4-fluoro-phen-yl)-4-(4-meth-oxy-phen-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one, C(25)H(24)FNO(5) (1), 3-(furan-2-yl)-4-(4-meth-oxy-phen-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one, C(23)H(23)NO(6) (2), 4-(4-meth-oxyphen-yl)-3-(naphthalen-1-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one, C(29)H(27)NO(5) (3), 3-(3,4-di-meth-oxy-phen-yl)-4-(4-meth-oxy-phen-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one, C(27)H(29)NO(7) (4) and 4,4-bis-(4-meth-oxy-phen-yl)-3-phenyl-1-(3,4,5-tri-meth-oxy-phen-yl)azetidin-2-one, C(32)H(31)NO(6) (5). All of the compounds are racemic. The lactam and 3,4,5-tri-meth-oxy-phenyl rings are approximately co-planar and the orientation of the lactam and the 4-meth-oxy-phenyl substituent is approximately orthogonal. The chiral centres, although eclipsed by geometry, have torsion angles ranging from -7.27 to 13.08° for the 3 position, and -8.69 to 13.76° for the 4 position of the β-lactam. The structures display intra-molecular C-H⋯O bonding between the 3,4,5-tri-meth-oxy-phenyl ring and the lactam ketone. Further C-H⋯O inter-actions are observed and form either an opposing meth-oxy 'buckle' to join two mol-ecules together or a cyclic dimer.