A new synthesis of pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones by oxidative N-N bond formation of 6-amino-5-(N-aryliminomethyl)uracils using iodobenzene diacetate

Synlett

Volumn , Issue 12, 1997, Pages 1409-1410

  Sajiki, Hironao ^a   Hattori, Kazuyuki ^a   Sako, Magoichi ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344740421     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1073     Document Type: Article

References (24)

1. For reviews on pyrazolopyrimidines, see: (a) Elnagdi, M. H.; Elmoghayar, M. R. H. "Chemistry of Pyrazolopyrimidines" in Advances in Heterocyclic Chemistry", Vol. 41, Katritzky, A. R. Ed., Academic Press, San Diego, 1987, pp. 319-376.
2. (b) Greehill, J. V. "Pyrazoles with Fused Six-membered Heterocyclic Rings" in "Comprehensive Heterocyclic Chemistry", Vol. 5, Katritzky, A. R.; Rees, C. W. Eds., Pergamon Press, Oxford, 1984, pp. 305-343.
3. Robins, R. K. J. Med. Chem. 1964, 7, 186.
4. (a) Mátyus, P.; Sohár., P.; Wamhoff, H. Heterocycles 1984, 22, 513.
5. (b) Garin, J.; Loscertales, M. P.; Meléandez, E.; Merchan, F. L.; Rodriguez, R.; Tejero, T. Heterocycles 1987, 26, 1303.
6. (c) Madronero, R.; Vega, S. Synthesis 1987, 628.
7. (d) Martin, D.; Gelbin, M. J. Prakt. Chem. 1987, 329, 753.
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9. (f) Molina, P.; Arques, A.; Vinader, M. V.; Becher, J.; Brondum, K. Idem J. Org. Chem. 1988, 53, 4654.
10. (g) Hosmane, R.S.; Lim, B. B. Synthesis 1988, 242.
11. (h) El-Reedy, A. M.; Ali, A. S.; Ayyad, A. O. J. Heterocycl. Chem. 1989, 26, 313.
12. (i) Bhuyan, P.; Boruah, R. C.; Sandhu, J. S. J. Org. Chem. 1990, 55, 568.
13. (j) Molina, P.; Arques, A.; Vinader, M. V. Synthesis 1990, 469.
14. (k) Guccinone, S.; Scolaro, L. M.; Russo, F. J. Heterocycl. Chem. 1996, 33, 459.
15. (l) Neidlein, R.; Wang, Z. Heterocycles 19 9 7, 45, 1509.
16. (a) Senda, S.; Hirota, K.; Yang, G.-N. Chem. Pharm. Bull. 1972, 20, 391.
17. (b) Senda, S.; Hirota, K.; Yang, G.-N. Idem Chem. Pharm. Bull. ibid. 1972, 20, 399.
18. (c) Yoneda, F.; Nagamatsu, T.; Nagamura, T.; Senga, K. J. Chem. Soc., Perkin Trans. 1 1977, 765.
19. (d) Senga, K.; Kanamori, Y.; Kanazawa, H.; Nishigaki, S. J. Heterocycl. Chem. 1978, 15, 359.
20. The creation of the N-N bond as the last step of the ring onstruction is common in indazoles and very rare in pyrazoles, see ref. (1b) p. 274. Recently, Kotali and Harris reported the synthesis of 2-arylaminoindazoles via oxidative N-N bond formation of o-aminoarylketone acylhydrazones with iodobenzene diacetate, Kotali, A.; Harris, P. A. J. Heterocycl. Chem. 1996, 33, 605.
21. Hirota, K.; Kitade, Y.; Sajiki, H.; Maki, Y. Synthesis 1984, 589.
22. Hirota, K.; Kubo, K.; Sajiki, H. Chem. Pharm. Bull. 1997, 45, 542.
23. Hirota, K.; Maruhashi, K.; Asao, T.; Kitamura, N.; Maki, Y.; Senda, S. Chem. Phann. Bull. 1983, 31, 3959.
24. Quite recently, Prakash et al. reported the synthesis of 3-substituted-2,1-benzisoxazoles involving oxidative N-O bond formation reaction with iodobenzene diacetate, Prakash, O.; Saini, R. K.; Singh, S. P.; Varma, R. S. Tetrahedron Lett. 1997, 38, 3147.