jo9b03402_si_001.pdf (4.08 MB)
Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines
journal contribution
posted on 2020-01-10, 16:43 authored by Derek
A. Leas, Yuxiang Dong, Jered C. Garrison, Xiaofang Wang, Edward L. Ezell, Douglas E. Stack, Jonathan L. Vennerstrom1-Substituted
and 1,1-disubstituted tetrahydro-β-carbolines
undergo sodium periodate oxidative ring expansion in the presence
of formaldehyde and other aldehydes to form 5,6-dihydro-7H-1,4-methanobenzo[e][1,4]diazonine-2,7(3H)-diones in 30–81% yield. In most cases, the reaction
to form this new 6/8/5-tricyclic ring system proceeds with high diastereoselectivity.
These benzannulated medium-ring keto imidazolidin-4-ones expand the
menu of tetrahydro-β-carboline oxidation products.