Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds

Yuji Matsuya; Noriko Ohsawa; Hideo Nemoto

doi:10.1021/ja065277z

Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds

Yuji Matsuya, Noriko Ohsawa, Hideo Nemoto^*

^*この論文の責任著者

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

46 被引用数 (Scopus)

抄録

Efficient transformations of benzocyclobutenones into 2,3-benzodiazepines by a formal insertion of diazomethylene compounds are described. This sequential process includes nucleophilic addition of diazomethylene anion, oxy-anion accelerated o-quinodimethane formation by an electrocyclic ring-opening reaction, and 8π-electrocyclization in one-pot under remarkably mild conditions. Intermediary oxy-anion plays an important role for the efficient transformations.

本文言語	英語
ページ（範囲）	13072-13073
ページ数	2
ジャーナル	Journal of the American Chemical Society
巻	128
号	40
DOI	https://doi.org/10.1021/ja065277z
出版ステータス	出版済み - 2006/10/11

ASJC Scopus 主題領域

触媒
化学一般
生化学
コロイド化学および表面化学

文献へのアクセス

10.1021/ja065277z

フィンガープリント

「Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{df98fc715ffb4599adbcf095e3878c3b,

title = "Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds",

abstract = "Efficient transformations of benzocyclobutenones into 2,3-benzodiazepines by a formal insertion of diazomethylene compounds are described. This sequential process includes nucleophilic addition of diazomethylene anion, oxy-anion accelerated o-quinodimethane formation by an electrocyclic ring-opening reaction, and 8π-electrocyclization in one-pot under remarkably mild conditions. Intermediary oxy-anion plays an important role for the efficient transformations.",

author = "Yuji Matsuya and Noriko Ohsawa and Hideo Nemoto",

year = "2006",

month = oct,

day = "11",

doi = "10.1021/ja065277z",

language = "英語",

volume = "128",

pages = "13072--13073",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "40",

}

Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds. / Matsuya, Yuji; Ohsawa, Noriko; Nemoto, Hideo.
In: Journal of the American Chemical Society, Vol. 128, No. 40, 11.10.2006, p. 13072-13073.

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

TY - JOUR

T1 - Facile transformation of benzocyclobutenones into 2,3-benzodiazepines via 4π-8π tandem electrocyclic reactions involving net insertion of diazomethylene compounds

AU - Matsuya, Yuji

AU - Ohsawa, Noriko

AU - Nemoto, Hideo

PY - 2006/10/11

Y1 - 2006/10/11

N2 - Efficient transformations of benzocyclobutenones into 2,3-benzodiazepines by a formal insertion of diazomethylene compounds are described. This sequential process includes nucleophilic addition of diazomethylene anion, oxy-anion accelerated o-quinodimethane formation by an electrocyclic ring-opening reaction, and 8π-electrocyclization in one-pot under remarkably mild conditions. Intermediary oxy-anion plays an important role for the efficient transformations.

AB - Efficient transformations of benzocyclobutenones into 2,3-benzodiazepines by a formal insertion of diazomethylene compounds are described. This sequential process includes nucleophilic addition of diazomethylene anion, oxy-anion accelerated o-quinodimethane formation by an electrocyclic ring-opening reaction, and 8π-electrocyclization in one-pot under remarkably mild conditions. Intermediary oxy-anion plays an important role for the efficient transformations.

UR - http://www.scopus.com/inward/record.url?scp=33749530710&partnerID=8YFLogxK

U2 - 10.1021/ja065277z

DO - 10.1021/ja065277z

M3 - 学術論文

C2 - 17017785

AN - SCOPUS:33749530710

SN - 0002-7863

VL - 128

SP - 13072

EP - 13073

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 40

ER -