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Abstract
Synthesis of the first representative of the linearly fused [1,2,3]triazolo[1,5-b]cinnolinium heteroaromatic cation as a quaternary salt is reported. Improved reaction conditions for preparation of some precursors have been elaborated. Reaction of the new heteroaromatic salt with nucleophiles resulted in regioselective formation of zwitterionic products.
Highlights
In the frame of our investigations on bridge-head nitrogen containing fused azolium salts we reported the synthesis of the linearly fused [1,2,3]triazolo[1,5-b]isoquinolinium salt (1, R1 = alkyl and aryl group, Ar = phenyl or substituted phenyl group
In this paper we report our efforts to synthesize this designed [1,2,3]triazolo[1,5-b]cinnolinium salt and to explore its reactivity with nucleophilic reagents
According to the earlier established protocol2, the synthesis of the desired model compound was planned by oxidative cyclization of cinnoline-3-ketones
Summary
3 was reacted first with dimethylformamide dimethylacetal to give an aminoenone (4), this compound was reacted with phenyldiazonium salt to afford the hydrazone 5 and, cyclization reaction under strongly acidic conditions resulted in formation of the cinnoline ketone (6). In both cases a zwitterionic addition product (10 and 11, respectively) separated from the reaction mixture.
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