New alkaloid derivatives by the reaction of 3,4-dihydro-β-carbolines with 1,3- dipoles; synthesis and a theoretical study[1]

Mátyás Milen, Péter Ábrányi-Balogh, Zoltán Mucsi, András Dancsó, T. Körtvélyesi, G. Keglevich

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The reaction of 3,4-dihydro-β-carboline derivatives with 1,3-dipoles, such as a nitrile imine and a nitrile oxide led to triazolopyridoindole and oxadiazolo-pyridoindole derivatives, respectively, that are novel synthetic alkaloids. Stereostructure, stability and further reactions of the pyridoindoles were also investigated. The oxadiazolo-pyridoindoles underwent reaction with a second unit of nitrile oxide to afford the corresponding trisubstituted 1,2,4-triazole 2-oxides. The mechanisms of the above reactions were studied in detail by high level quantum chemical calculations. It was found that the reaction of the 1,3-dipoles is not an expected 1,3-cycloaddition, but rather a stepwise addition reaction. The exact mechanism was found to be dependent on the substitution pattern.

Original languageEnglish
Pages (from-to)1811-1825
Number of pages15
JournalCurrent Organic Chemistry
Volume15
Issue number11
Publication statusPublished - Jun 2011

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Carbolines
Nitriles
Alkaloids
Derivatives
Oxides
Lead oxide
Addition reactions
Imines
Cycloaddition
Substitution reactions

Keywords

  • β-carbolines
  • Cycloaddition
  • Mechanism
  • Nitrile imine
  • Nitrile oxide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

New alkaloid derivatives by the reaction of 3,4-dihydro-β-carbolines with 1,3- dipoles; synthesis and a theoretical study[1] . / Milen, Mátyás; Ábrányi-Balogh, Péter; Mucsi, Zoltán; Dancsó, András; Körtvélyesi, T.; Keglevich, G.

In: Current Organic Chemistry, Vol. 15, No. 11, 06.2011, p. 1811-1825.

Research output: Contribution to journalArticle

Milen, Mátyás ; Ábrányi-Balogh, Péter ; Mucsi, Zoltán ; Dancsó, András ; Körtvélyesi, T. ; Keglevich, G. / New alkaloid derivatives by the reaction of 3,4-dihydro-β-carbolines with 1,3- dipoles; synthesis and a theoretical study[1] In: Current Organic Chemistry. 2011 ; Vol. 15, No. 11. pp. 1811-1825.
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AU - Körtvélyesi, T.

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