An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2-b]Pyrrole and Indeno[1,2-c]Pyridazine

Vladimir L. Gein, Natalia V. Nosova, Andrei N. Yankin, Alina Y. Bazhina, Maksim V. Dmitriev

Research output

Abstract

A highly efficient and simple synthesis of a number of pharmaceutically interesting functionalized indenopirrole derivatives has been developed via the reaction of ninhydrin and acetoacetic acid amides in ethanol at the absence of catalyst at room temperature. In the case, then N,N-dialkylacetoacetamides were used as the methylene components, novel N,N-dialkyl-3-oxobutanamide derivatives were received. The novel indenopyridazine derivatives were first obtained via the reaction of indenopirroles with hydrazine. Environmental friendliness, mild reaction conditions, simple work-up avoiding chromatographic purification, and excellent yields are the important features of this protocol.

Original languageEnglish
JournalPolycyclic Aromatic Compounds
Early online date17 Apr 2019
DOIs
Publication statusPublished - 2019

Fingerprint

Pyrroles
hydrazine
Derivatives
Ninhydrin
Hydrazine
Amides
Purification
Ethanol
Catalysts
Acids
pyridazine
Temperature

Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

Cite this

Gein, Vladimir L. ; Nosova, Natalia V. ; Yankin, Andrei N. ; Bazhina, Alina Y. ; Dmitriev, Maksim V. / An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2-b]Pyrrole and Indeno[1,2-c]Pyridazine. In: Polycyclic Aromatic Compounds. 2019.
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abstract = "A highly efficient and simple synthesis of a number of pharmaceutically interesting functionalized indenopirrole derivatives has been developed via the reaction of ninhydrin and acetoacetic acid amides in ethanol at the absence of catalyst at room temperature. In the case, then N,N-dialkylacetoacetamides were used as the methylene components, novel N,N-dialkyl-3-oxobutanamide derivatives were received. The novel indenopyridazine derivatives were first obtained via the reaction of indenopirroles with hydrazine. Environmental friendliness, mild reaction conditions, simple work-up avoiding chromatographic purification, and excellent yields are the important features of this protocol.",
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author = "Gein, {Vladimir L.} and Nosova, {Natalia V.} and Yankin, {Andrei N.} and Bazhina, {Alina Y.} and Dmitriev, {Maksim V.}",
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An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2-b]Pyrrole and Indeno[1,2-c]Pyridazine. / Gein, Vladimir L.; Nosova, Natalia V.; Yankin, Andrei N.; Bazhina, Alina Y.; Dmitriev, Maksim V.

In: Polycyclic Aromatic Compounds, 2019.

Research output

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T1 - An Eco-Friendly Stereoselective Synthesis of Novel Derivatives of Indeno[1,2-b]Pyrrole and Indeno[1,2-c]Pyridazine

AU - Gein, Vladimir L.

AU - Nosova, Natalia V.

AU - Yankin, Andrei N.

AU - Bazhina, Alina Y.

AU - Dmitriev, Maksim V.

PY - 2019

Y1 - 2019

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KW - Heterocycles

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KW - N,N-dialkyl-3-oxobutanamides

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KW - ANALOGS

KW - QUATERNARY STEREOCENTERS

KW - CYCLIZATIONS

KW - 1,3-DIPOLAR CYCLOADDITION

KW - CONSTRUCTION

KW - GAMMA-LACTAMS

KW - SYSTEMS

KW - ACETYLCHOLINESTERASE INHIBITORS

KW - LIGAND

KW - TRANSFORMATIONS

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