The nucleophilic substitution of 2,3-dicyanopyrazine (1) with allylamine is useful for the construction of pteridine ring. A methanopterin analogue, 1-allyl-6-(mesitylamino)methyl-7-methy-3-phenylpteridine (12), was synthesised by this method from 2,3-dicyano-5-hydroxymethyl-6-methylpyrazine (5) deriving from 2,3-dicyanopyrazine (1).
PfleidererW., Comprehensive Heterocyclic Chemistry, ed by KatritzkyA.R., and ReesC. W., Pergamon Press, Oxford, 1984, vol. 3, Part 2B, pp. 325–327.
2.
TempleC.Jr., and MontgomeryJ. A., Chemistry and Biochemistry of Folates, ed by BlackleyR.L., and BenkovicS. J., John Wiley and Sons, New York, 1984, vol. 1, pp. 61–120.
3.
DiMarcoA.A., BobikT. A., and WolfeR. S., Ann. Rev. Biochem., 1990, 59, 355.
4.
BrownD.J., Fused Pyrimidines, Part 3, Pteridines, John Wiley and Sons, New York, 1988.
5.
TsuzukiK., and TadaM., J. Heterocycl. Chem., 1985, 22, 1365.
6.
(a) TsuzukiK., and TadaM., J. Heterocycl. Chem., 1986, 23, 1299.
7.
IgarashiM., and TadaM., Heterocycles, 1994, 38, 2277. (c) M. Tada, Y. Asawa and M. Igarashi, J. Heterocycl. Chem., 1997, 34, 973.
8.
GuibeF., Tetrahedron, 1998, 54, 2967 (Review).
9.
SatoN., and TakeuchiR., Synthesis, 1990, 659.
10.
AlbertA., BrownD. J., and CheesemanG., J. Chem. Soc., 1952, 4219.
