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

Journal of the American Chemical Society

Volumn 128, Issue 40, 2006, Pages 13072-13073

  Matsuya, Yuji ^a   Ohsawa, Noriko ^a   Nemoto, Hideo ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKADIENE; ANION; AROMATIC COMPOUND; AZO COMPOUND; BENZENE DERIVATIVE; BENZOCYCLOBUTENONE; BENZODIAZEPINE DERIVATIVE; CARBENOID; CYCLOBUTANE DERIVATIVE; CYCLOBUTANONE DERIVATIVE; DIAZEPINE DERIVATIVE; DIAZOMETHYLENE; INDANONE DERIVATIVE; KETONE; LEWIS ACID; METHANE; NITROGEN; OXIDE; PYRAZOLE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DECOMPOSITION; DESILYLATION; DIELS ALDER REACTION; ELECTRON; LITHIATION; MOLECULAR STABILITY; ORGANIC CHEMISTRY; RING OPENING; SYNTHESIS; THERMAL EXPOSURE; TRANSITION TEMPERATURE;

BENZODIAZEPINES; DIAZOMETHANE; KETONES; POLYCYCLIC COMPOUNDS;

EID: 33749530710     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065277z     Document Type: Article

References (22)

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22. A retroreaction to release the diazomethylene anion is responsible for the somewhat lower yield of 6b (69%) than that expected, which is supported by the isolation of the ketone 1b (30% yield) from the reaction medium. This implies that the initial nucleophilic addition step is in equilibrium, and therefore, 3.0 equiv of lithiodiazoacetate was used to increase the adduct form.