Reaction of 5-(3,4-dimethoxyphenyl)pyrazine-2,3-dicarbonitrile with alkyl radicals

The reaction of 5-(3,4-dimethoxyphenyl)pyrazine-2,3-dicarbonitrile (Ib) with alkyl radicals gives addition products at the C(6)-position of the pyrazine ring as the intermediates which collapse into substitution products, 6-alkyl-5-(3,4-dimethoxyphenylpyrazine-2,3-dicarbonitrile (II), under oxidative conditions. Under non-oxidative conditions the intermediate is converted into dihydropyrazine derivatives, 6-alkyl-(3,4-dimethoxy-phenyl)-5,6-dihydropyrazine-2,3-dicarbonitrile (III), and 3,6-disubstituted pyrazine derivatives, 3,6-dialkyl-5-(3,4-dimethoxyphenyl)pyrazine-2-carbonitrile (IV) and 3-acyl-6-alkyl-5-(3,4-dimethoxyphenyl)pyrazine-2-carbonitrile (V).

[1]  M. Tada,et al.  Photochemistry of host-guest complexes. VIII: The photoreaction of pyrazinedicarbonitrile derivatives having a crown ether moiety in the presence of an ω-diethylamino-1-alkanaminium salt , 1985 .

[2]  M. Tada,et al.  PHOTOPRODUCTS FROM 5-ARYLPYRAZINE-2,3-DICARBONITRILE, STRUCTURE REVISION FOR THE MAIN PRODUCT , 1984 .

[3]  F. Minisci,et al.  ELECTRON-TRANSFER PROCESSES: PEROXYDISULFATE, A USEFUL AND VERSATILE REAGENT IN ORGANIC CHEMISTRY , 2002 .

[4]  B. Giese.  Formation of CC Bonds by Addition of Free Radicals to Alkenes , 1983 .

[5]  M. Tada,et al.  The Photochemistry of the Host-Guest Complex. VII. The Photoreaction of Dicyanopyrazine Derivatives Having a Crown Ether Moiety , 1982 .

[6]  M. Tada,et al.  The substitution reaction of pyrazine-2,3-dicarbonitrile derivatives with ammonia, amines, water and alcohols , 1982 .

[7]  F. Minisci,et al.  NUCLEOPHILIC CHARACTER OF THE ALKYL RADICALS. 19. 1A ABSOLUTE RATE CONSTANTS IN THE HOMOLYTIC ALKYLATION OF PROTONATED HETEROAROMATIC BASES BY N-BUTYL AND TERT-BUTYL RADICALS , 1980 .

[8]  Z. Aizenshtat,et al.  An improved synthesis of carbocyclic and heterocyclic arene imines , 1980 .

[9]  M. Tada,et al.  EFFECT OF GUEST CATION ON THE PHOTOREACTIVITY OF THE PYRAZINE DERIVATIVES HAVING CROWN ETHER MOIETY , 1980 .

[10]  T. Matsuda,et al.  Photochemical reductive acylation and oxidative acyl activation on phenazine and related nitrogen heterocycles. , 1980 .

[11]  T. Caronna,et al.  Nucleophilic character of acyl radicals. Substituent effects on the homolytic acylation of protonated heteroaromatic bases , 1972 .