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Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-?-carbolines.

ABSTRACT: 1-Substituted and 1,1-disubstituted tetrahydro-?-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-?-carboline oxidation products.

SUBMITTER: Leas DA

PROVIDER: S-EPMC7092372 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines.

Leas Derek A DA Dong Yuxiang Y Garrison Jered C JC Wang Xiaofang X Ezell Edward L EL Stack Douglas E DE Vennerstrom Jonathan L JL

The Journal of organic chemistry 20200110 4

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 produ ...[more]

PMID: 31904963

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