Summary
Several 7-methyl-5-alkyl-2-vinylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones were prepared. The successful cyclization and alkylation of 6-(α-methylbenzylidenehydrazino)-1-methyluracils2a–d using dimethylformamide acetals at high temperature provided6a–d,7a–d, and8a–d. Treatment of6a–d and7a–d with acid afforded 7-methyl-5-alkylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones9a,b; under the same conditions,3a–d reacted to 7-methylpyrazolo[3,4-d]-pyrimidine-4,6(5H)-dione (4) in good yield.
Zusammenfassung
Es wurden verschiedene 7-Methyl-5-alkyl-2-vinylpyrazolo[3,4-d]pyrimidin-4,6(5H,7H)-dione hergestellt. Cyclisierung und Alkylierung der 6-(α-Methylbenzylidenhydrazino)-1-methyl-uracile2a–d mit Hilfe von Dimethylformamidacetalen bei hohen Temperaturen ergab6a–d,7a–d und8a–d. Behandlung von6a–d und7a–d mit Säure lieferte die 7-Methyl-5-alkylpyrazolo[3,4-d]pyrimidin-4,6(5H,7H)-dione9a,b; unter den gleichen Bedingungen reagierten3a–d in guter Ausbeute zu 7-Methylpyrazolo[3,4-d]pyrimidin-4,6(5H)-dion (4).
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Skipper EH, Robins KR, Thomson RJ (1995) Proc Soc Exp Biol and Med89: 594
Skipper EH, Robins KR, Thomson RJ, Cheng CC, Brockman, WR, Schabel MF Jr (1957) Cancer Research17: 579
Nelson JD, Lafon WS, Tuttle VJ, Mitler HW, Krenitsky AT, Elion GB, Berens LR, Marr JJ (1979) J Biol Chem254: 11544; Berens LR, Marr JJ, Nelson JD, Lafon WS (1980) Biochem Pharmacol29: 2397
Mecht MS, Werner D (1973) J Chem Soc Perkin 1, 1903
Senda S, Hirota K, Yang G-N (1972) Chem Pharm Bull20: 391, 399
Miyashita A, Ijima C, Higashino T (1990) Heterocyles31: 1309
Pfleiderer W, Schundehutte HK (1958) Liebigs Ann Chem712: 158
Maki Y, Izuta K, Suzuki M (1971) Chem Commun: 1442
Yoneda F, Nagamatsu T, (1974) Heterocycles2: 153
Senga K, Kanamori Y, kanazawa H, Nishigaki S (1978) J Heterocycl Chem15: 359
Zemlicka J (1970) Coll Czech Chem Commun35: 3572
Holy A, Bald R, Hong DN (1971) Coll Czech Chem Commun36: 2658
Youssif S, Assy M (1996) J Chem Res (S) 442, (M) 2546
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Youssif, S. DMF acetals as alkylating and cyclizing agents: A facile route to substituted pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones. Monatsh Chem 128, 493–501 (1997). https://doi.org/10.1007/BF00806857
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00806857