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

Derek A. Leas, Yuxiang Dong, Jered C. Garrison, Xiaofang Wang, Edward L. Ezell, Douglas E. Stack, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2846-2853
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number4
DOIs
StatePublished - Feb 21 2020

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ASJC Scopus subject areas

  • Organic Chemistry

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