Two Cyano Groups in 2,3,5,6-Tetracyanopyrazine

The diamine 105 has been prepared by this method for use as a comonomer in the preparation of polyureas (74MI1). 

Primary aliphatic amines give two products when substitution of two cyano groups is attempted. One is the normal 2,6-disubstitution product and the other is the result of one substitution of, and one addition to, a cyano group. 

Primary aromatic amines give only the latter product, the structure of which was determined by X-ray crytallography for the p-toluidine-derived product 106 (83UP1). 

When DISN reacts with electron-rich styrenes such as p-methoxystyrene, good yields of reduced pyrazines 117, often accompanied by their oxidized forms, are obtained. However, reaction with electron-deficient styrenes like p-fluorostyrene give the 2-amino-3-(2-arylaziridin-l-yl)maleonitriles (118) (72JA3242 84JOC813). 

Reaction of DAMN with 1,2-Oriented Ketones, Aldehydes, Esters, Acids, Acetals, Ketals, Sulfoxides, Oximies, and gew-DiHALioEs 

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