Dicyclopenta[a,d]cycloocten: ein [14]Annulen mit zwei überbrückenden Einfachbindungen

Synthesis of 2-aminofuran derivatives with azulene or N,N-dimethylanilino substituent was established by the formal [2 + 2] cycloaddition-retroelectrocyclization of 3-(1-azulenyl or N,N-dimethylanilino)-2-propyn-1-ols with tetracyanoethylene, followed by the intramolecular nucleophilic addition to the initially formed tetracyanobutadiene moiety of the internal hydroxyl group that come from 2-propyn-1-ol. The reaction proceeds under mild conditions with short reaction period. The products of the reaction are readily available with simple purification procedure. 2-Aminofuran derivatives obtained by this reaction were revealed to be convertible to 6-aminofulvene derivatives with the treatment of various amines. The structure of 2-aminofuran and 6-aminopentafulvene with N,N-dimethylanilino substituent was confirmed by single crystal X-ray structural analysis.

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Synthesis of 2‐Aminofurans by Sequential [2+2] Cycloaddition–Nucleophilic Addition of 2‐Propyn‐1‐ols with Tetracyanoethylene and Amine‐Induced Transformation into 6‐Aminopentafulvenes

Shoji

Nagai

Tanaka

et al. 2017

Chemistry A European J

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Molecular Transformation to Pyrroles, Pentafulvenes, and Pyrrolopyridines by [2+2] Cycloaddition of Propargylamines with Tetracyanoethylene

Shoji

Takagaki

Ariga

et al. 2020

Chemistry A European J

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In this paper,w ed escribe an efficient and atomeconomicals ynthesis of highly functionalized pyrroles, pentafulvenes, and pyrrolopyridinesb y[ 2 + +2] cycloaddition-retroelectrocyclization of N-substituted propargylamines with tetracyanoethylene,f ollowed by the treatment of the resultingt etracyanobutadiened erivatives with silica gel. In this reaction, silica gel plays an important role to promote the intramolecular cyclization to afford the heterocyclic products from the tetracyanobutadiene intermediates. The products were obtaineds electively depending on the substituent on the nitrogen atom of the starting propargylamines.Scheme1.Our previous study and planneds trategy to access highly functionalized pyrrole derivatives.[a] Prof.

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Dicyclopenta[a,d]cycloocten: ein [14]Annulen mit zwei überbrückenden Einfachbindungen

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References 27 publications

Synthesis of 2‐Aminofurans by Sequential [2+2] Cycloaddition–Nucleophilic Addition of 2‐Propyn‐1‐ols with Tetracyanoethylene and Amine‐Induced Transformation into 6‐Aminopentafulvenes

Synthesis of 2‐Aminofurans by Sequential [2+2] Cycloaddition–Nucleophilic Addition of 2‐Propyn‐1‐ols with Tetracyanoethylene and Amine‐Induced Transformation into 6‐Aminopentafulvenes

Molecular Transformation to Pyrroles, Pentafulvenes, and Pyrrolopyridines by [2+2] Cycloaddition of Propargylamines with Tetracyanoethylene

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