Details

Autor(en) / Beteiligte

• Chen, Yi-Hua
• Yang, Jing
• Lu, Zi-Han
• Zhao, Ke-Hua
• Xie, Qi-Ying
• Yan, Sheng-Jiao

Titel

Synthesis of benzo[][1,5]diazocin-6(5)-one derivatives the Cu-catalysed oxidative cyclization of 2-aryl-1-indoles with 1,1-enediamines

Ist Teil von

• Chemical communications (Cambridge, England), 2023-01, Vol.59 (9), p.1217-122

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A novel protocol for the synthesis of highly functionalized benzo[ b ][1,5]diazocin-6(5 H )-one derivatives (BDCOs, 4 and 5 ) from 2-aryl-1 H -indoles and 1,1-enediamines was developed via a complex cascade of reactions including regioselective free radical oxidation, the 1,2-addition of imine, imine-enamine tautomerization, intramolecular cyclization, and ring expansion. The cascade reaction was enabled by refluxing a mixture of two substrates in the presence of di- tert -butyl peroxide (DTBP) as an oxidant and anhydrous CuI as a catalyst in toluene under argon protection. Consequently, a series of BDCOs ( 4 and 5 ) were synthesized with high regioselectivity in good yield. This protocol can be used for the synthesis of functionalized BDCOs via a one-pot oxidative annulation reaction rather than a multi-step reaction, which is suitable for both combinatorial and parallel syntheses of BDCOs. A novel protocol for the synthesis of highly functionalized benzo[ b ][1,5]diazocin-6(5 H )-one derivatives (BDCOs, 4 and 5 ) from 2-aryl-1 H -indoles and 1,1-enediamines was developed via a complex cascade of reactions.