Details

Autor(en) / Beteiligte

• Li, Fei
• Gu, Xiao‐Juan
• Zeng, Chang‐E.
• Li, Xia
• Liu, Bo
• Huang, Guo‐Li

Titel

Copper(I)/Bpy‐Catalyzed C‐2‐H Benzylation of Quinazolin‐4(3H)‐ones with N‐Tosylhydrazones

Ist Teil von

• European journal of organic chemistry, 2020-05, Vol.2020 (19), p.2923-2928

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A general and efficient copper‐catalyzed C–H benzylation reaction of quinazolin‐4(3H)‐ones with N‐tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross‐coupling occurs at the electron‐poor C‐2 position of quinazolin‐4(3H)‐one and represents an exceedingly practical method to afford 2‐benzylated quinazolin‐4(3H)‐ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late‐stage functionalization of advanced synthetic intermediates. Regioselective C‐2‐H benzylation of quinazolin‐4(3H)‐ones with N‐tosylhydrazones in a ligand dependent copper system was studied. An array of substituted quinazolin‐4(3H)‐ones were coupled effectively with a wide variety of N‐tosylhydrazones derived from aryl ketones to afford the alkylated products in moderate to good yields. This is a useful, time‐efficient, and scalable procedure for the construction of C(sp2)–C(sp3) bonds.