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IJOC> Vol.5 No.4, December 2015
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Utility of Styrylpyrazoloformimidate in the Synthesis of Fused Heterocyclic Compounds

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DOI: 10.4236/ijoc.2015.54021    3,061 Downloads   3,621 Views   Citations
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Hamdi M. Hassaneen*, Zakaria Ahmed Gomaa

Affiliation(s)

Department of Chemistry, Faculty of Science, Cairo University, Giza, Egypt.

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.

KEYWORDS

(Z)-N'-Phenylcinnamohydrazonoyl Chloride, (E)-5-Amino-1-Phenyl-3-Styryl-1H-Pyrazole-4-Carbonitrile, Formimidate, Dimroth Rearrangement

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.

Conflicts of Interest

The authors declare no conflicts of interest.

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