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

doi:10.1021/acs.joc.9b03402

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	2846-2853
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	85
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.9b03402
State	Published - Feb 21 2020

ASJC Scopus subject areas

Organic Chemistry

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title = "Tricyclic Imidazolidin-4-ones by Witkop Oxidation of Tetrahydro-β-carbolines",

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.",

author = "Leas, {Derek A.} and Yuxiang Dong and Garrison, {Jered C.} and Xiaofang Wang and Ezell, {Edward L.} and Stack, {Douglas E.} and Vennerstrom, {Jonathan L.}",

note = "Funding Information: We acknowledge the U.S. National Institutes of Health (AI116723-01) for financial support. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = feb,

day = "21",

doi = "10.1021/acs.joc.9b03402",

language = "English (US)",

volume = "85",

pages = "2846--2853",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "4",

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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

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 4

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

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