Add time:08/22/2019         Source:sciencedirect.com

Treatment of 3-aminoisoquinoline (1) with aryldi-azonium salts gave 2-amino-4-arylazoisoquinolines (2) which reacted with aromatic aldehyde to yield imidazo(4,5-c) iso-quinolines. With 3-amino-4-methylisoquinoline (4), however, the same reaction led to 3-isoquinolyltriazenes (5), and these could then be cyclized by the use of “TBB” to give tetrazolo(1,5-b)-isoquinolinium salts (6). The latter azolium salt (6) showed ambident reactivity in the presence of hydroxide ion manifested by simultaneous formation of tolualdehyde derivative 10 and indazolo (3,2-b) isoquinoline system (8). This ambidency as well as the difference in behaviour between the new linearly fused system (6) and its formerly studied angularly fused isomers (“annelation effect”) is interpreted in terms of the frontier molecular orbital theory.

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