A photoredox-promoted approach for the synthesis of [1,4]diazepino[1,7-a]indol-6(7H)-ones starting from N-indolyl phenylacrylamides and aroyl chlorides as radical source is reported. This method, that involves a cascade radical addition on C−C double bond followed by intramolecular cyclization at indole C2-position, affords two diastereomeric indole-fused 1,4-diazepinones characterized by a N−C(aryl) axial chirality in yields ranging from 51 to 99%.
Synthesis of Indole‐Fused 1,4‐Diazepinones via Photoredox‐Catalyzed Cascade Cyclization Reaction / E. Brambilla, S. Meraviglia, E. Moneta, D. Nava, S. Rizzato, G. Abbiati, V. Pirovano. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - (2023), pp. 1-10. [Epub ahead of print] [10.1002/adsc.202300708]
Synthesis of Indole‐Fused 1,4‐Diazepinones via Photoredox‐Catalyzed Cascade Cyclization Reaction
E. Brambilla
Primo
;S. MeravigliaSecondo
;D. Nava;S. Rizzato;G. AbbiatiPenultimo
;V. Pirovano
Ultimo
2023
Abstract
A photoredox-promoted approach for the synthesis of [1,4]diazepino[1,7-a]indol-6(7H)-ones starting from N-indolyl phenylacrylamides and aroyl chlorides as radical source is reported. This method, that involves a cascade radical addition on C−C double bond followed by intramolecular cyclization at indole C2-position, affords two diastereomeric indole-fused 1,4-diazepinones characterized by a N−C(aryl) axial chirality in yields ranging from 51 to 99%.
| File | Dimensione | Formato | |
|---|---|---|---|
|
Adv Synth Catal - 2023 - Brambilla - Synthesis of IndoleE28090Fused 1 4E28090Diazepinones via PhotoredoxE28090Catalyzed Cascade_compressed.pdf
accesso aperto
Tipologia:
Publisher's version/PDF
Dimensione
986.86 kB
Formato
Adobe PDF
|
986.86 kB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
