Synthesis of a novel tripyrrindione and its thio analog

ORGN 372

Sanjeev K. Dey, deys@unr.nevada.edu and David A. Lightner. Department of Chemistry MS 216, University of Nevada, 1664 North Virginia Street, Reno, NV 89557-0216
Tripyrrindiones are a rare class of tripyrrolic compounds that are typically red-violet pigments. They were first reported in the synthetic work of Fischer and Alder in 1931 directed toward the synthesis of mesobilirubin XIIIα. Very little work has been done involving the synthesis of this class of compounds. Since 1931 there are only 5-6 additional tripyrrindiones appeared in the literature.

Therefore, we were attracted to further investigate simple tripyrrindiones. The synthesis and physical properties of one such tripyrrindione containing methoxy groups will be presented alongwith its crystal structure. Also the change in its physical properties by replacing lactams with thiolactams will be presented.