Synthesis of novel 13a-(o-aminoalkyl)-8-oxoberbines by means of reaction of homophthalic anhydride with 1-substituted 3,4-dihydroisoquinolines. An unexpected formation of a pyrrolo[3,4-i]berbindione

Elena Stanoeva, Angelina Georgieva, Stanislava Avramova, Nikola Burdzhiev, L. Lázár

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Abstract

The reaction of 1-[o-(N-acylated amino)alkyl]-3,4-dihydroisoquinolines (7a-e) with homophthalic anhydride (1) leads to the formation of 8-oxo-13a-[(N-acylated amino)alkyl]-8H-dibenzo[a,g]quinolizine- 13-carboxylic acids (8a-e) with predomination of cis diastereomers, together with small amount of trans-8a. cis-13a-[(N-Cbzaminomethyl)]-8-oxo-dibenzoquinolizine-13-carboxylic acid (8a) cyclized to the unknown dibenzo[a,g]pyrrolo[3,4-i]quinolizinedione (10) upon moderate heating in methanol.

Original languageEnglish
Pages (from-to)130-135
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume52
Issue number1
DOIs
Publication statusPublished - 2015

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Anhydrides
Carboxylic Acids
Quinolizines
Methanol
Heating
G 1616

ASJC Scopus subject areas

  • Organic Chemistry

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Synthesis of novel 13a-(o-aminoalkyl)-8-oxoberbines by means of reaction of homophthalic anhydride with 1-substituted 3,4-dihydroisoquinolines. An unexpected formation of a pyrrolo[3,4-i]berbindione. / Stanoeva, Elena; Georgieva, Angelina; Avramova, Stanislava; Burdzhiev, Nikola; Lázár, L.

In: Journal of Heterocyclic Chemistry, Vol. 52, No. 1, 2015, p. 130-135.

Research output: Contribution to journalArticle

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