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Utility of Styrylpyrazoloformimidate in the Synthesis of Fused Heterocyclic Compounds

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DOI: 10.4236/ijoc.2015.54021    2,939 Downloads   3,401 Views  

ABSTRACT

Refluxing of (E)-5-amino-1-phenyl-3-styryl-1H-pyrazole-4-carbonitrile 2 with triethylor-thoformate in acetic anhydride afforded the corresponding formimidate 3. Treatment of 3 with hydrazine hydrate in ethanol afforded amino imino compound 4. Reaction of 4 with diethyl dicarbonate at reflux gave (E)-7-phenyl-9-styryl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 7. Refluxing of 4 with hydrazine hydrate afforded (E)-4-hydrazinyl-1-phenyl-3-styryl-1H-pyrazolo[3,4-d] pyrimidine 8. Treatment of the latter compound 8 with aldehydes in boiling ethanol in the presence of acetic acid afforded the corresponding hydrazone 10. Oxidative cyclization of the hydrazone 10 led to the formation of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidine 11. The latter products re-arranged to pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines 13. The structures of the new products were established on the basis of elemental analysis and spectral data.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Hassaneen, H. and Gomaa, Z. (2015) Utility of Styrylpyrazoloformimidate in the Synthesis of Fused Heterocyclic Compounds. International Journal of Organic Chemistry, 5, 213-222. doi: 10.4236/ijoc.2015.54021.

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