Copper(II)-mediated cascade oxidative C-C coupling and aromatization: Synthesis of 3-hydroxyphenanthridinone derivatives
A novel copper(II) acetate mediated synthesis of 3-hydroxyphenanthridin- 6(5H)-ones from N-(3-oxocyclohex-1-enyl)benzamides was developed. The process is postulated to involve an intramolecular oxidative C(sp2)-C(sp 3) bond formation
Yu, Qingzhen,Zhang, Nan,Tang, Yang,Lu, Hang,Huang, Jianhui,Wang, Songqing,Du, Yunfei,Zhao, Kang
supporting information; experimental part
p. 2374 - 2384
(2012/09/07)
Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones
A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.