Studies on diazepines. XVIII. Photochemical synthesis of 3H-1,3-benzodiazepines from quinoline N-acylimides.

Tsuchiya, Takashi; Okajima, Shunzo; Enkaku, Michiko; Kurita, Jyoji

doi:10.1248/cpb.30.3757

Cited by 6 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The mechanism of ring expansion is proposed to involve initial formation of a 3membered diazirane by attack of the exocyclic nitrogen onto C(2) of the quinoline, followed by NÀ N cleavage, aziridine formation and finally CÀ C cleavage to give the benzodiazepine. [83] Subsequent treatment of the benzodiazepine with aqueous HCl afforded the ring opened amido-enamine (Scheme 11,D); further Scheme 8. Ring expansion of benzisoxazoles through Rh-catalyzed cycloaddition with 2-azidoketones.…”

Section: Ring Contractionmentioning

confidence: 99%

“…Tsuchiya and co‐workers reported that good yields were obtained for quinoline N ‐amides bearing electron‐donating substituents at the 6‐ or 8‐position, whereas electron‐poor substrates suffered from deleterious N−N bond cleavage. The mechanism of ring expansion is proposed to involve initial formation of a 3‐membered diazirane by attack of the exocyclic nitrogen onto C(2) of the quinoline, followed by N−N cleavage, aziridine formation and finally C−C cleavage to give the benzodiazepine [83] . Subsequent treatment of the benzodiazepine with aqueous HCl afforded the ring opened amido‐enamine ( Scheme 11 ,D ); further treatment with HCl and heating at 80 °C resulted in the formation of the 1‐acyl indole.…”

Section: Ring Contractionmentioning

confidence: 99%

See 1 more Smart Citation

Skeletal Editing: Interconversion of Arenes and Heteroarenes

Joynson

Ball

2023

Helvetica Chimica Acta

View full text Add to dashboard Cite

Skeletal editing involves making specific point‐changes to the core of a molecule through the selective insertion, deletion or exchange of atoms. It thus represents a potentially powerful strategy for the step‐economic modification of complex substrates and is a perfect complement to methods such as C−H functionalization that target the molecular periphery. Given their ubiquity in biologically active compounds, the ability to perform skeletal editing on – and therefore interconvert between – aromatic heterocycles is especially valuable. This review summarizes both recent and key historical examples of skeletal editing as applied to interconversion of aromatic rings; we anticipate that it will serve to highlight not only the innovative and enabling nature of current skeletal editing methods, but also the tremendous opportunities that still exist in the field.

show abstract

Section: Ring Contractionmentioning

confidence: 99%

Section: Ring Contractionmentioning

confidence: 99%