Stereochemistry of 1,3-dipolar-cycloaddition of 3,4-dihydroisoquinoline- and 3,4-dihydro-carboline-N-methoxycarbonyl- and N-phenacyl-methylides with maleic and fumaric nitrile

István Kádas, Gábor Szántó, L. Tőke, A. Simon, Gábor Tóth

Research output: Contribution to journalArticle

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Abstract

(Chemical Equation Presented) The 1,3-dipolar-cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7-b]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1H and 13C assignments have been achieved by a combination of various one- and two-dimensional NMR experiments.

Original languageEnglish
Pages (from-to)1373-1381
Number of pages9
JournalJournal of Heterocyclic Chemistry
Volume44
Issue number6
Publication statusPublished - Nov 2007

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Carbolines
Nitriles
Stereochemistry
Cycloaddition
Alkaloids
Nuclear magnetic resonance
Derivatives
Experiments
G 1616
indole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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abstract = "(Chemical Equation Presented) The 1,3-dipolar-cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7-b]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1H and 13C assignments have been achieved by a combination of various one- and two-dimensional NMR experiments.",
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T1 - Stereochemistry of 1,3-dipolar-cycloaddition of 3,4-dihydroisoquinoline- and 3,4-dihydro-carboline-N-methoxycarbonyl- and N-phenacyl-methylides with maleic and fumaric nitrile

AU - Kádas, István

AU - Szántó, Gábor

AU - Tőke, L.

AU - Simon, A.

AU - Tóth, Gábor

PY - 2007/11

Y1 - 2007/11

N2 - (Chemical Equation Presented) The 1,3-dipolar-cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7-b]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1H and 13C assignments have been achieved by a combination of various one- and two-dimensional NMR experiments.

AB - (Chemical Equation Presented) The 1,3-dipolar-cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7-b]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1H and 13C assignments have been achieved by a combination of various one- and two-dimensional NMR experiments.

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