Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones

Kenji Sugimoto; Rie Hayashi; Hideo Nemoto; Naoki Toyooka; Yuji Matsuya

doi:10.1021/ol301474g

Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones

Kenji Sugimoto, Rie Hayashi, Hideo Nemoto, Naoki Toyooka, Yuji Matsuya^*

^*この論文の責任著者

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

30 被引用数 (Scopus)

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Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.

本文言語	英語
ページ（範囲）	3510-3513
ページ数	4
ジャーナル	Organic Letters
巻	14
号	13
DOI	https://doi.org/10.1021/ol301474g
出版ステータス	出版済み - 2012/07/06

ASJC Scopus 主題領域

生化学
物理化学および理論化学
有機化学

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10.1021/ol301474g

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title = "Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones",

abstract = "Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.",

author = "Kenji Sugimoto and Rie Hayashi and Hideo Nemoto and Naoki Toyooka and Yuji Matsuya",

year = "2012",

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T1 - Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones

AU - Sugimoto, Kenji

AU - Hayashi, Rie

AU - Nemoto, Hideo

AU - Toyooka, Naoki

AU - Matsuya, Yuji

PY - 2012/7/6

Y1 - 2012/7/6

N2 - Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.

AB - Efficient monocyclic 1,2-diazepine formation via a tandem electrocyclization reaction of cyclobutenones with lithiodiazoacetate is demonstrated. The reaction proceeds through an oxy anion-accelerated 4π-ring opening of cyclobutene followed by an 8π-ring closure of the resultant oxy anion-substituted diazo-diene under mild conditions to furnish a 1,2-diazepine via formal diazomethylene insertion into the C-C bond of cyclobutenone.

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U2 - 10.1021/ol301474g

DO - 10.1021/ol301474g

M3 - 学術論文

C2 - 22721410

AN - SCOPUS:84863615228

SN - 1523-7060

VL - 14

SP - 3510

EP - 3513

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Efficient approach to 1,2-diazepines via formal diazomethylene insertion into the C-C bond of cyclobutenones

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