Isoquinoline-fused polycyclic compound 3-

Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation Yusuke Ohta, Yushi Kubota, Tsuyoshi Watabe, Hiroaki Chiba, Shinya Oishi, Nobutaka Fujii and Hiroaki Ohno J. Org. Chem. 2009, 74, 6299-6302. Reproduced with permission... 

Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four Component Coupling, Cascade Cyclization, and Oxidation... 

In conclusion, the author has developed a novel route to isoquinoline-fused polycyclic compounds by a four-component coupling and cascade cyclization strategy. In this reaction, the cyclization/oxidation step can be accelerated by use of an oxygen atmosphere, giving rise to improved yields of the cyclized products in many cases. Because this four-component reaction catalytically forms one carbon-carbon and four carbon-nitrogen bonds producing only H2O and H2 as the... 

Table 4 Synthesis of (Aminomethyl)isoquinoline-fused polycyclic compounds...

General Procedure for Synthesis of (Aminomethyl)isoquino-line-Fused Polycyclic Compounds by Domino Mannich-Type Reaction and Cascade Cyclization Synthesis o/6-/(N,N-Diisopropylamino)methyl]-3,4-dihydro-2H-pyrimido[2,l-SL] isoquinoline (12a) (Table 1, Entry 10)... 

In relation to the three-component indole formation, a novel four-component synthesis of 3-(aminomethyl)isoquinoline was developed. The reaction of 2-ethynylbenzaldehyde with (HCHO) , secondary amine, and t-BuNH2 proceeds through Mannich-type reaction, cycUzation, and elimination of t-butyl group. By the use of alkane diamine instead of r-BuNH2, 3-(aminomethyl)isoquino-line-fused polycyclic compounds were also synthesized by cascade cycUzation and oxidation. Changing the carbon tether of the diamine component led to the synthesis of isoquinoUnes fused with various heterocycles. 

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