Abstract
Phenylazocyanothioacetamide1 reacts with malononitrile to afford the pyridinethione4 which reacts with phenacylbromide to yield the pyridine-S-phenacyl derivative6. 1 reacts with ethyl cyanoacetate to yield the pyridazine derivative,8, and with phenacyl bromide to afford the N-phenacyl derivative11, instead of the thiazole10. Compound11 afforded the pyrazolopyridine13 on reaction with malononitrile while10 was obtained on coupling of the thiazole14 with diazotised aniline. Compound10 reacts with malononitrile to afford the thiazolyl pyridazine15. Compound1 reacts with malononitrile dimer to afford the pyridopyridazine derivative17a. 1 reacts also with active methylene heterocycles to afford the pyrazolo and thiazolo-fused pyridazines20 and23, respectively.
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Abdelrazek, F. M., Salah, A. M., Elbazza, Z. E., Synthesis of novel thieno-[2,3-d] pyrimidine, thieno[2,3-b]pyridine and thiazolo[3-2,a]thieno[2,3-d]-pyrimidine derivatives and their effect of the production of Mycotosin.Arch Pharm. (Weinheim), 325, 301–305 (1992).
Elnagdi, M. H., Abdelrazek, F. M., Ibrahim, N. S., Erian, A. W., Studies on alkylheteroaromatic compounds. The reactivity of polyfunctionally substituted azines towards electrophilic reagents.Tetrahedron, 45(11), 3597–3604 (1989).
Elnagdi, M. H., Ghozlan, S. A. S.M Abdelrazek, F. M., Seliem, M. A., Studies with polyfunctionally substituted heterocycles., Synthesis of new thiopyrans, pyridines, pyrans and their fused derivatives with other ring systems.J. Chem. Res. (s), 116–117 (1991).
Fanmy, S. M., Mohareb, R. M., Cyanothioacetamide in heterocyclic synthesis., A novel synthesis of 2-pyridothione derivatives.Tetrahedron, 42, 687–690 (1986).
Kandeel, Z. E., Abdelrazek, F. M., Elnagdi, M. H., Torgoman, A. M., Nitriles in heterocyclic systhesis., New youte for the synthesis of pyridine and pyrido[2,3-d] pyridazine derivatives.Heterocycles, 24(9), 2455–2461 (1986).
Schafer, H., Gewald, K., Zur chemie des 4-phenylthiazolyl-(2)-acetonitrils.J. Prakt. Chem., 316, 684–692 (1974).
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Negm, A.M., Abdelrazek, F.M., Elnagdi, M.H. et al. Heterocyclic synthesis with nitriles: New routes for synthesis of pyridazines, pyridines and their fused derivatives. Arch. Pharm. Res. 17, 411–414 (1994). https://doi.org/10.1007/BF02979116
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DOI: https://doi.org/10.1007/BF02979116