Using l-Alkoxycarbonyl-2-cyanobenzenes as Substrates

The cyclocondensation of these substrates with hydrazines is represented by only one example. Methyl o-cyanobenzoate (116) with methylhydrazine gave 4-amino-2-methyl-l(2H)-phthalazinone (117) (MeONa, MeOH, 20°C, 12 h 24%).  

The use of phthalonitiiles as substrates has not been developed to any extent, but existing examples are interesting. Thus phthalonitrile (118) with an excess of hydrazine gave 1,4-dihydrazinophthalazine (120), perhaps by transamination of the initial product (119) (AcOH, dioxane, reflux, 3 h 83% or AcOH, H2O, dioxane. 

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