Condensed Isoquinolines. 17. Enamine Properties of Benzimidazo[1,2-b]isoquinolin-11(5H)-one in Alkylation Reactions

Visible-Light-Promoted Radical Cascade Cyclization of 2-Vinyl Benzimidazoles: Access to Benzo[4,5]imidazo[1,2-b]isoquinolin- 11(6H)-ones

“…Yellow oily liquid (25.3 mg, 70%); 1 H NMR (400 MHz, CDCl 3 ) δ 8.57 −8.46 (m, 1H), 8.26 (s, 1H), 7.88−7.80 (m, 1H), 7.61−7.55 (m, 2H), 7.53−7.43 (m, 2H), 3.90 (q, J = 6.4 Hz, 2H), 2.94−2.82 (m, 1H), 2.67−2.52 (m, 1H), 2.51 (s, 3H), 1.93 (s, 3H), 1.88−1.72 (m, 2H), 1.11 (t, J = 7.2 Hz, 3H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 172. 3, 160.6, 158.2, 142.9, 141.3, 138.0, 135.9, 131.3, 129.2, 125.9, 125.4, 124.9, 119.6, 115.9, 60.5, 41.5, 39.4, 31.1, 30.2, 21.0, 14. Ethyl 3- (6,5] imidazo- [1,2-b]isoquinolin-6-yl)propanoate (3d). Yellow oily liquid (33.3…”

“…Direct C6-alkylation of benzimidazo- isoquinolinone appears a facile strategy to achieve 6-substituted benzimidazoisoquinolinones. Nevertheless, due to competitive N / C -alkylation, this tactic was primarily applicable to C6-diallylated derivatives rather than other alkylated compounds (Scheme b) . In 2021, Li’s group presented a trifluoromethyl-benzimidazolylation of olefins, resulting in the synthesis of 6-methyl-6-(2,2,2-trifluoroethyl)­benzimidazo­[1,2- b ]­isoquinolin-11­(6 H )-one with a 93% yield (Scheme c) .…”

Condensed isoquinolines 25. Alkylation of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one

“…3,9-dioxo-3H,9H,11H-benzo [5,6] We have previously studied alkylation, one of the characteristic reactions of enamines, using benzimidazo[1,2-b]isoquinolin-11(5H)-one [2,3] and 7,12-dihydro-5H-isoquino[2,3-a]quinazolin-5-one [4,5] as examples. It seemed of interest to investigate the characteristics of this reaction for the linear isomer -6,11-dihydro-13H-isoquino [3,2-b]quinaxolin-13-one (1) which had been shown previously [1] to be ambident as nucleophilic agent with the example of reactions with carbonyls.…”