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16.14.1.5.1.1 Method 1: From a 2,3-Diaminoacrylonitrile and an Aldehyde or Ortho Ester

DOI: 10.1055/sos-SD-016-00919

Sato, N.Science of Synthesis, (200416774.

(E,E)-3-Amino-2-(benzylideneamino)-3-methoxyacrylonitrile (95), prepared by treatment of aminomalononitrile4-toluenesulfonic acid complex with benzaldehyde in methanol containing sodium acetate, undergoes cyclization with ortho esters to form 3-methoxy-6-phenylpyrazine-2-carbonitrile derivatives 96 in 4391% yield (Scheme 30).[‌185‌] When triethyl orthoacetate is used, intermediate 97 is isolated (in 35% yield), and quantitatively converts into pyrazine 96 by treatment with pyridine or triethylamine. Reaction of acrylonitrile 95 with an arylaldehyde in place of the ortho ester affords 6-aryl-2-methoxy-5-phenylpyrazines 98 in good yield.

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