Abstract
Diazotised 5-amino-3-methyl-4-phenyloyrazole (1) reacted with active methylene reagents and with β-naphthol to yield the pyrazolo[1,5-c)-1,2,4-triazine derivatives2a-e and5. Compound1 reacted with benzoyl isothiocyanate and with phenyl isothiocyanate to yield the corresponding pyrazol-5-ylthiourea derivatives6a, b. 5a was converted into the thiourea derivative8 by the action of acids or alkalies. A synthesis of 2-methyl-3-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]-pyrimidin-5-one from the reaction of α-phenylacetoactonitrile (3-oxo-2-phenyl-butyric nitrile) and β-cyanoethylhydrazine is reported.
Zusammenfassung
Diazotiertes 5-Amino-3-methyl-4-phenylpyrazol (1) reagiert mit einer aktiven Methylenkomponente und β-Naphthol zu den Pyrazolo[1,5-c]-1,2,4-triazin-Derivaten2a-e und5. 1 ergibt mit Benzoylisothiocyanat und Phenylisothiocyanat die entsprechenden Pyrazol-5-yl-thioharnstoffe6a, b. 5a wurde mittels Säure oder Base in das Thioharnstoffderivat8 umgewandelt. Es wird über eine Synthese von 2-Methyl-3-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]-pyrimidin-5-on aus α-Phenylacetoacetonitril (3-Oxo-2-phenyl-butyronitril) und β-Cyanoethylhydrazin berichtet.
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References
H. Ochi, T. Miyasaka, K. Kanada, andK. Arakowa, Bull. Chem. Soc. Japan49, 1980 (1976).
S. Hecht, D. Werner, D. D. Traficant, M. Sundanalingam, P. Prusinger, T. Eto, andT. Sakurai, J. Org. Chem.40, 1815 (1975).
J. D. Ratajczyk andL. R. Swett, J. Heterocyclic Chem.12, 517 (1975).
B. M. Lynch, M. A. Khan, S. C. Sharma, andH. C. Teo, Canad. J. Chem.53, 119 (1975).
I. Ito, Japan, 7030, 101 (1970) Chem. Abstr.74, 22827 (1971).
A. Takamizowa andH. Sato, Japan72, 45353 (1972); Chem. Abstr.78, 58454 (1973).
T. Novinson, R. K. Robins, andD. E. O'Brien, J. Heterocyclic. Chem.10, 887 (1973).
W. B. Jolley, T. Novinson, P. M. Scholtz, L. N. Simond, andD. E. O'Brien, Fifth international congress on pharmacology volunteer abstracts, Abstract 697, San Francisco, California, July 1972.
T. Novinson, R. M. K. Dimmitt, L. N. Simon, R. K. Robins, andD. E. O'Brien, J. Med. Chem.17, 645 (1974).
H. A. Dewald, S. Lovvestael, andD. C. Buuter, J. Med. Chem.20, 1562 (1977).
W. E. Kirkpatrick, T. Okabe, W. Hillyard, R. K. Robins, A. T. Dran, andT. Novinson, J. Med. Chem.20, 386 (1977).
M. H. Elnagdi, M. R. H. Elmoghayar, E. M. Kandeel, andM. K. A. Ibraheim, J. Heterocyclic Chem.14, 227 (1977); and references therein.
M. H. Elnagdi, M. R. H. Elmoghayar, D. H. Fleita, E. A. Hafez, andS. M. Fahmy, J. Org. Chem.41, 3781 (1976).
M. H. Elnagdi, M. R. H. Elmoghayar, S. M. Fahmy, M. K. A. Ibraheim, andH. H. Alnima, Z. Naturforsch.33 b, 216 (1978).
H. Reimlinger andA. von Overstaeten, Chem. Ber.99, 3350 (1966).
M. H. Elnagdi, S. M. Fahmy, M. R. H. Elmoghayar, andZ. M. Kandeel, J. Heterocyclic Chem.15 (1978 in press).
M. H. Elnagdi, E. M. Kandeel, andM. R. H. Elmoghayar, Z. Naturforsch.32 b, 307 (1977).
M. H. Elnagdi, E. M. Zayed, E. M. Kandeel, andS. M. Fahmy, Z. Naturforsch.32 b, 430 (1977).
M. H. Elnagdi, Tetrahedron30, 2791 (1974).
M. H. Elnagdi, D. H. Fleita, andM. R. H. Elmoghayar, Tetrahedron31, 63 (1975).
M. H. Elnagdi andM. Ohta, Bull. Chem. Soc. Japan46, 1830 (1973).
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Elnagdi, M.H., Zayed, E.M., Khalifa, M.A.E. et al. Reactions with heterocyclic amidines, VII: Synthesis of some new pyrazolo[1,5-c]-1,2,4-triazines, pyrazolo[1,5-a]-1,3,5-triazines and pyrazolo[1,5-a]pyrimidines. Monatshefte für Chemie 112, 245–252 (1981). https://doi.org/10.1007/BF00911090
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DOI: https://doi.org/10.1007/BF00911090