Chemistry of indoles carrying a basic function. Part IX. Unexpected cyclizations of diketones derived from Uhle's ketone

István Moldvai, E. Gács-Baitz, Eszter Temesvári-Major, Mária Incze, L. Poppe, Csaba Szántay

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Starting from a tricyclic diketone (14) obtained by Bowman's method, a tetracyclic oxonaphthalene derivative (17) has been prepared through intramolecular aldol condensation followed by indole → naphthalene isomerization. An unexpected formation of a lactol ether (16) was observed as a result of acidic treatment of 14. Two modified reaction sequences starting from N-methyl derivatives have also been presented. The keto ketal (26) gave a macrocyclic lactol (27) with unexpected structure as a result of deketalization with trimethylsilyl iodide. The formation of a tetracyclic lactam (37) was observed while applying the modified Reformatsky reaction to ketone (33).

Original languageEnglish
Pages (from-to)153-175
Number of pages23
JournalHeterocycles
Volume64
DOIs
Publication statusPublished - Dec 31 2004

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Indoles
Lactams
Cyclization
Ketones
Ether
Derivatives
Isomerization
Condensation
3-hydroxybutanal
trimethylsilyl iodide
indole
naphthalene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chemistry of indoles carrying a basic function. Part IX. Unexpected cyclizations of diketones derived from Uhle's ketone. / Moldvai, István; Gács-Baitz, E.; Temesvári-Major, Eszter; Incze, Mária; Poppe, L.; Szántay, Csaba.

In: Heterocycles, Vol. 64, 31.12.2004, p. 153-175.

Research output: Contribution to journalArticle

Moldvai, István ; Gács-Baitz, E. ; Temesvári-Major, Eszter ; Incze, Mária ; Poppe, L. ; Szántay, Csaba. / Chemistry of indoles carrying a basic function. Part IX. Unexpected cyclizations of diketones derived from Uhle's ketone. In: Heterocycles. 2004 ; Vol. 64. pp. 153-175.
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AU - Incze, Mária

AU - Poppe, L.

AU - Szántay, Csaba

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