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^*

^*Corresponding author for this work

Synthetic and Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

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.

Original language	English
Pages (from-to)	13072-13073
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	128
Issue number	40
DOIs	https://doi.org/10.1021/ja065277z
State	Published - 2006/10/11

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja065277z

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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",

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doi = "10.1021/ja065277z",

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journal = "Journal of the American Chemical Society",

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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.

Research output: Contribution to journal › Article › peer-review

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.

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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 -

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

Abstract

ASJC Scopus subject areas

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