title: 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.
abstract: Synthesis of 2-aminofuran derivatives with an 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 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 through a simple purification procedure. 2-Aminofuran derivatives obtained by this reaction could be converted into 6-aminofulvene derivatives upon reaction with various amines. The structures of 2-aminofuran and 6-aminopentafulvene with a N,N-dimethylanilino substituent were confirmed by single-crystal X-ray structural analysis.
authors.affiliation: Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
authors.forename: Taku
authors.identifier: http://orcid.org/0000-0001-8176-2389
authors.initials: T
authors.lastname: Shoji
authors.affiliation: Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
authors.forename: Daichi
authors.initials: D
authors.lastname: Nagai
authors.affiliation: Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
authors.forename: Miwa
authors.initials: M
authors.lastname: Tanaka
authors.affiliation: Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
authors.forename: Takanori
authors.initials: T
authors.lastname: Araki
authors.affiliation: Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto, 390-8621, Nagano, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Ohta
authors.affiliation: Graduate School of Science and Technology, Hirosaki University, Hirosaki, 036-8561, Aomori, Japan.
authors.forename: Ryuta
authors.initials: R
authors.lastname: Sekiguchi
authors.affiliation: Graduate School of Science and Technology, Hirosaki University, Hirosaki, 036-8561, Aomori, Japan.
authors.forename: Shunji
authors.initials: S
authors.lastname: Ito
authors.affiliation: Advanced Research Support Center, Ehime University, Matsuyama, 790-8577, Ehime, Japan.
authors.forename: Shigeki
authors.initials: S
authors.lastname: Mori
authors.affiliation: Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Ehime, Japan.
authors.forename: Tetsuo
authors.identifier: http://orcid.org/0000-0002-6552-2606
authors.initials: T
authors.lastname: Okujima
keywords: azulene; cycloaddition; nucleophilic addition; oxygen heterocycles; synthetic methods