TY - JOUR
T1 - Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines
AU - Leas, Derek A.
AU - Dong, Yuxiang
AU - Garrison, Jered C.
AU - Wang, Xiaofang
AU - Ezell, Edward L.
AU - Stack, Douglas E.
AU - Vennerstrom, Jonathan L.
PY - 2020/2/21
Y1 - 2020/2/21
N2 - 1-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.
AB - 1-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.
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U2 - 10.1021/acs.joc.9b03402
DO - 10.1021/acs.joc.9b03402
M3 - Article
C2 - 31904963
AN - SCOPUS:85078470154
VL - 85
SP - 2846
EP - 2853
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -