Iodine mediated rearrangement of tetraarylpiperidin-4-ones: Synthesis, structure analysis and biological studies of 5-aryl-2-methoxy-2,4-diphenyl-1H-pyrrole-3-ones.

An interesting iodine/methanol mediated rearrangement of tetraaylpiperidin-4-ones to 2-methoxy-2,4,5-triaryl-1 H -pyrrole-3-ones is described. The structural features of the products are investigated by spectral data and single crystal X-ray analysis. The antifungal, antibacterial and antioxidant characteristics of the synthesized compounds have been studied. Image 1 • Conversion of tetraarylpiperidin-4-ones to 5-aryl-2-methoxy-2,4-diphenyl-pyrrole-3-ones in presence of I 2 /MeOH is reported. • The mechanism for the ring contraction rearrangement is proposed. • Synthesized new compounds have been characterized by 1D, 2D NMR and SC-XRD techniques. • Synthesized new compounds exhibit good antimicrobial, antifungal and antioxidant properties. [ABSTRACT FROM AUTHOR]