Synthesis of Annulated [gamma]-Lactams via Intramolecular 1,3-Dipolar Cycloadditions of Functionalized N-Allyl [alpha]-Diazo Amides

N-Allyldiazoacetamides containing a phosphinyl group at the α-position underwent the intramolecular 1,3-cycloaddition, followed by 1,3-hydrogen shift to afford 6a-diethoxyphosphinyl-3a,4,5,6a-tetrahydropyrrolo[3,4-c]pyrazol-6(1H)-ones in 74--78% yields, while the corresponding α-phenylthio amide pro...

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Published inBulletin of the Chemical Society of Japan Vol. 66; no. 5; p. 1496
Main Authors Minami, Toru, Kamitamari, Masashi, Utsunomiya, Tomohisa, Tanaka, Tetsuya, Ichikawa, Junji
Format Journal Article
LanguageEnglish
Published Tokyo Chemical Society of Japan 01.05.1993
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Abstract N-Allyldiazoacetamides containing a phosphinyl group at the α-position underwent the intramolecular 1,3-cycloaddition, followed by 1,3-hydrogen shift to afford 6a-diethoxyphosphinyl-3a,4,5,6a-tetrahydropyrrolo[3,4-c]pyrazol-6(1H)-ones in 74--78% yields, while the corresponding α-phenylthio amide produced 1-phenylthio-3-azabicyclo[3.1.0]hexan-2-one in 74% yield via extrusion of N2 from the intramolecular 1,3-cycloadduct. In the application of these compounds to the conversion of functionality, the former gave a fused tricyclic heterocycle and the latter gave deallylated compounds.
AbstractList N-Allyldiazoacetamides containing a phosphinyl group at the α-position underwent the intramolecular 1,3-cycloaddition, followed by 1,3-hydrogen shift to afford 6a-diethoxyphosphinyl-3a,4,5,6a-tetrahydropyrrolo[3,4-c]pyrazol-6(1H)-ones in 74--78% yields, while the corresponding α-phenylthio amide produced 1-phenylthio-3-azabicyclo[3.1.0]hexan-2-one in 74% yield via extrusion of N2 from the intramolecular 1,3-cycloadduct. In the application of these compounds to the conversion of functionality, the former gave a fused tricyclic heterocycle and the latter gave deallylated compounds.
Author Ichikawa, Junji
Tanaka, Tetsuya
Minami, Toru
Kamitamari, Masashi
Utsunomiya, Tomohisa
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Title Synthesis of Annulated [gamma]-Lactams via Intramolecular 1,3-Dipolar Cycloadditions of Functionalized N-Allyl [alpha]-Diazo Amides
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