Copper-Catalyzed Domino Strategy Construction of Fused Benzopyrroloazepinone through the Reaction of Allenyloximes and Arylboronic Acids

Ejiyeh, Negah; Amiri, Kamran; Bijarkani, Fatemeh; Hosseini, S.; Fouladi, Vahid; Fathi, Azar; Bijanzadeh, Hamid; Rominger, Frank; TANYELİ, CİHANGİR; Balalaie, Saeed

doi:10.1021/acs.orglett.6c01767

Copper-Catalyzed Domino Strategy Construction of Fused Benzopyrroloazepinone through the Reaction of Allenyloximes and Arylboronic Acids

Ejiyeh N. E., Amiri K., Bijarkani F. H., Hosseini S. S., Fouladi V., Fathi A., ...Daha Fazla

Organic Letters, cilt.28, sa.24, ss.7641-7644, 2026 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Kısa Makale
Cilt numarası: 28 Sayı: 24
Basım Tarihi: 2026
Doi Numarası: 10.1021/acs.orglett.6c01767
Dergi Adı: Organic Letters
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
Sayfa Sayıları: ss.7641-7644
Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

Herein, we present a novel strategy for the efficient synthesis of fused azepinone frameworks from allene-tethered oximes and arylboronic acids through a domino effect comprising a Chan–Lam coupling, [3 + 2] cycloaddition, [3,3]-sigmatropic rearrangement, and imine–enamine tautomerization with good to excellent yields. This straightforward reaction proceeds through the consecutive formation of a C–N, C–O, and two C–C bonds. This approach exhibits a broad substrate scope, excellent functional group tolerance, and scalability to gram quantities.