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

[1]   Wolkoff, P. (1975) A New Method of Preparing Hydrazonoyl Halides. Canadian Journal of Chemistry, 53, 1333-1335.
http://dx.doi.org/10.1139/v75-183

[2]   Shawali, A.S. and Abdel Hamid, A.O. (1976) Reaction of Dimethyiphenacyl-sulfonium Bromide with N-Nitrosoace-tarylamides and Reactions of the Products with Nucleophiles. Bulletin of the Chemical Society of Japan, 49, 321.
http://dx.doi.org/10.1246/bcsj.49.321

[3]   Farag, A.M. and Algharib, M.S. (1988) Synthesis and Reactions of C-(2-Thenoyl)-N-Arylformhydrazidoyl Bromides. Organic Preparations and Procedures International: The New Journal for Organic Synthesis, 20, 521-526.
http://dx.doi.org/10.1080/00304948809356298

[4]   Eweiss, N.F. and Osman, A. (1980) Synthesis of Heterocycles. Part II. New Routes to Acetylthiadiazolines and Alkylazothiazoles. Journal of Heterocyclic Chemistry, 17, 1713-1717.
http://dx.doi.org/10.1002/jhet.5570170814

[5]   Hassaneen, H.M., Shawali, A.S., Elwan, N.M. and Abounada, N.M. (1992) Reaction of 1-(2-Naphthoyl)methyl-2-di-methylsulfonium Bromide with N-Nitroso-N-arylacetamides and Reactions of the Products with Some Nucleophiles. Sulfur Letters, 13, 273-285.

[6]   Shawali, A.S. and Parkanyi, C. (1980) Hydrazidoyl Halides in the Synthesis of Heterocycles. Journal of Heterocyclic Chemistry, 17, 833-854.
http://dx.doi.org/10.1002/jhet.5570170501

[7]   Shawali, A.S. and Sherif, S.M. (2007) The Chemistry of Hydrazonates. Current Organic Chemistry, 11, 773.
http://dx.doi.org/10.2174/138527207780831747

[8]   Shawali, A.S. and Hassaneen, H.M. (1977) ArylAlkanehydrazonates and Their Thio Analogs. Synthesis of Some 2-Alkyl Derivatives of 4H-1,3,4-Benzoxadiazines and 4H-1,3,4-Benzothiadiazines. Bulletin of the Chemical Society of Japan, 50, 2827.
http://dx.doi.org/10.1246/bcsj.50.2827

[9]   Gouma, S.M., Salah, T.A. and Abdel Hamid, A.O. (2015) Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole. Monatshefte für Chemie, 146, 149-158.

[10]   Gouma, S.M., Ahmed, S.A. and Abdel Hamid, A.O. (2015) Synthesis, Characterization and Pharmacological Evaluation of Some Novel Thiadiazoles and Thiazoles Incorporating Pyrazole Moity As Anticancer Agents. Molecules, 20, 1357-1376.

[11]   Hassaneen, H.M., Shawali, A.S., Abdallah, T.A. and Saleh, F.M. (2014) Synthesis and Cycloaddition Reactions of 4,4-dimethyl-2,6-dioxocyclohexane-thiocarboxamides with Nitrilimines. ARKIVOC, 2014, 155-169.

[12]   Hassaneen, H.M., Shetta, A.H., Elwan, N.M. and Shawali, A.S. (1982) Reaction of Phenyltrichloromethane with Semicarbazide and Thiosemicarbazide Derivatives. Heterocycles, 19, 1477-1482.
http://dx.doi.org/10.3987/R-1982-08-1477

[13]   Hassaneen, H.M., Mousa, H.A.H. and Shawali, A.S. (1987) Chemistry of C-Heteroarylnitrilimines. Synthesis and Cycloaddition Reactions of N-phenyl-C-(2-thienyl)nitrilimine. Journal of Heterocyclic Chemistry, 24, 1665-1668.
http://dx.doi.org/10.1002/jhet.5570240633

[14]   Hassaneen, H.M. and Mousa, H.A.H. (1988) C-(2-Thienyl)-N-Arylformohydrazidoyl Chlorides in the Synthesis of Selenadiazolines and Thiadiazolines. Sulfur Letters, 7, 93.

[15]   Hassaneen, H.M., Shawali, A.S. and Elwan, N.M. (1990) Synthesis and Cycloaddition Reaction of N-Phenyl-C-Sty- rylmethanohydrazonyl Bromide. Heterocycles, 31, 247-253.
http://dx.doi.org/10.3987/COM-89-5045

[16]   Hassaneen, H.M., Shawali, A.S. and Elwan, N.M. (1990) A Convenient Synthesis of 3,5’-Bipyrazolyl Derivatives via Hydrazonyl Halides. Heterocycles, 31, 1041-1047.
http://dx.doi.org/10.3987/COM-90-5310

[17]   Hassaneen, H.M., Hilal, R.H., Elwan, N.M., Harhash, A. and Shawali, A.S. (1984) The Regioselectivity in the Formation of Pyrazolines and Pyrazoles from Nitrile Imines. Journal of Heterocyclic Chemistry, 21, 1013-1016.
http://dx.doi.org/10.1002/jhet.5570210417

[18]   Baraldi, P.G., Elkashef, H., Farghaly, A., Vanelle, P. and Fruttarolo, F. (2004) Synthesis of New Pyrazolo[4,3-e]- 1,2,4-triazolo[1,5-c]pyrimidines and Related Heter-ocycles. Tetrahedron, 60, 5093-5104.
http://dx.doi.org/10.1016/j.tet.2004.04.010

[19]   Nagamatsu, T. and Fujita, T. (1999) Facile and General Syntheses of 3- and/or 5-Substituted 7H-pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidines as a New Class of Potential Xanthine Oxidase Inhibitors. Chemical Communications, 16, 1461.

[20]   Seifi, N., Niaki, M.H.Z., Barzegari, M.R., Davoodnia, A., Zhiani, R. and Kaju, A.A. (2006) Synthesis of 8-aryl-1H- pyrazolo[4,3-e][1,2,4]triazolo[4,3-a] Pyrimidine-4(5H)-imine by Using the Preyssler’s Anion [NaP5W30O110]14- as a Green and Eco-Friendly Catalyst. Journal of Molecular Catalysis A: Chemical, 260, 77-81.
http://dx.doi.org/10.1016/j.molcata.2006.06.043

[21]   Elwan, N.M. (1989) Synthesis and Reactivity of Some Nitrogen Heterocyclic System via Dipolar Cycloadditions. Ph.D. Thesis, Cairo University, Giza City.

[22]   Rashad, A.E., Heikel, O.A., El-Nezhawy, A.O.H. and Abdel-Megeid, F.M.E. (2004) Synthesis and Isomerization of Thienotriazolopyrimidine and Thienotetrazolopyrimidine Derivatives with Potential Anti-Inflammatory Activity. Heteroatom Chemistry, 16, 226-234.
http://dx.doi.org/10.1002/hc.20114

[23]   Abdelfattah, B., Kandeel, M.M., Abdel-Hakeem, M. and Fahmy, Z.M. (2006) Synthesis of Certain Fused Thienopyrimidines of Biological Interest. Journal of the Chinese Chemical Society, 53, 403-412.
http://dx.doi.org/10.1002/jccs.200600051

 
 
Top