Isoquinolinones, fused

The synthesis of 3-substituted isoquinolinones and fused isoquinolinones can be performed by the photoinduced SRN1 reactions in DMSO of o-iodobenzamide with the enolates of acyclic aromatic and aliphatic ketones and cyclic ketones, respectively. These reactions proceed from moderate to good yields (Schemes 10.47 and 10.48) [65],... 

The photostimulated reactions with the enolate anions of 1-indanone and a-tetra-lone lead to the reduction product benzamide (23% and 44%, respectively), together with the target fused isoquinolinones (51% and 42%, respectively) [65]. The formation of benzamide can probably be ascribed to the hydrogen atom abstraction from the cyclic ketone. 

The synthesis of 3-substituted isoquinolinones can be performed by the photoinduced Sj j. 1 reactions in DMSO of o-iodobenzamide 40 with enolate ions of aromatic and aliphatic ketones in 68-87% yields. With cyclic ketones, the reactions afforded fused isoquinolinones 41 and 42 with good yields (Scheme 10.8) [37]. 

Similar ideas have also been used for the assembly of benzo-fused pyridones and pyridines. For example, the pyridone 180 was initially transformed into the desired diene 181 required for the RCM reaction. Exposure of 181 to the 1-Ru catalyst allowed for the formation of intermediate 182, which upon dehydrosulfonation readily yielded the isoquinolinone 183 (Scheme 17.35) [61]. 

Recently, Guchhait and Madaan have reported the synthesis of N-fused imidazole-amines 380 and isoquinolinone-imidazoles 381 by employing 2-aminopyridine 6g, Izb, and various aldehydes (e.g., 9zb, 9zc) in the GBB-4C-3CR (Scheme 7.117) [125],... 

SCHEME 7.117 Synthesis of Af-fused imidaz le-amines (380) and isoquinolinone-imidazole (381) using Izb. 

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