Versatile synthesis and fungicidal activities of 6-amino-3-alkylthio-1,5- dihydro-1-phenyl-pyrazolo [3,4-d]pyrimidin-4-one derivatives

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 179, Issue 10, 2004, Pages 2039-2050

  Wang, Hong Qing ^a,b   Liu, Zhao Jie ^a   Ding, Ming Wu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b UNIVERSITY OF SOUTH CHINA   (China)

Author keywords

Aza Wittig reaction; Fungicidal activities; Pyrazolo 3,4 d pyrimidin 4 one; Synthesis

Indexed keywords

3 BENZYLTHIO 6 PHENYLAMINO 1 PHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 3 METHYLTHIO 6 PHENYLAMINO 1 PHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (2 PYRIDINEMETHYLAMINO) 3 BENZYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (2 PYRIDINEMETHYLAMINO) 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (2 THIOPHENEMETHYLAMINO) 3 BENZYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (2 THIOPHENEMETHYLAMINO) 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (3 PYRIDINEMETHYLAMINO) 3 BENZYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (3 PYRIDINEMETHYLAMINO) 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (4 FLUOROBENZYLAMINO) 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (ISOPROPANYLYLAMINO) 3 BENZYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 (PROPANYLAMINO) 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; 6 [2 (1 ETHYLPYRROLIDINE)METHYLAMINO] 3 METHYLTHIO 1,5 DIPHENYL 1,5 DIHYDROPYRAZOLO[3,4 D]PYRIMIDIN 4 ONE; ALIPHATIC AMINE; CYANAMIDE; DIBROMOTRIPHENYLPHOSPHORANE; ESTER DERIVATIVE; IMINOPHOSPHORANE; ISOCYANIC ACID DERIVATIVE; PHENYL GROUP; PHOSPHORANE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; FUNGICIDAL ACTIVITY; WITTIG REACTION;

EID: 7644221994     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500490474897     Document Type: Article

References (30)

1. A. Bendich, P. J. Russell, and J. J. Fox, J. Am. Chem. Soc., 76, 6073-6077 (1954).
2. S. Kobayashi, Chem. Pharm. Bull., 21, 941-945 (1973).
3. a) A. Ali, G. E. Taylor, and D. W. Graham, PTC Int. Appl. (WO) 0129045 (2001);
4. b) A. Ali, G. E. Taylor, and D. W. Graham, Chem. Abstr., 134, 311225u (2001).
5. a) S. A. Armstrong, J. M. Berge, P. Brown, J. S. Elder, A. K. Forrest, D. W. Hamprecht, and R. L. Jarvest, PTC Int. Appl. (WO) 0071, 524, (2000);
6. b) S. A. Armstrong, J. M. Berge, P. Brown, J. S. Elder, A. K. Forrest, D.W. Hamprecht, and R. L. Jarvest, Chem. Abstr., 134, 17496z (2001).
7. E. R. EI-Bendary and F. A. Badria, Arch. Pharm., 333(4), 99-103 (2000).
8. a) A. Tetsuya, M. Shogo, I. Fumio, Y. Masuo, and N. Masafuml, Eur. Pat. Appl. (EP) 0733633 (1996);
9. b) A. Tetsuya, M. Shogo, I. Fumio, Y. Masuo, and N. Masafuml, Chem. Abstr., 125, 328725u (1996).
10. a) B. A. Dumaitre and N. Dodic, Eur. Pat. Appl. (EP) 636,626, (1994);
11. b) B. A. Dumaitre and N. Dodic, Chem. Abstr., 123, 228202m (1995).
12. a) S. F. Campbell, A. R. Mackenzie, and A. Wood, PTC Int. Appl. (WO) 16644 (1996);
13. b) S. F. Campbell, A. R. Mackenzie, and A. Wood, Chem. Abstr., 125, 105160e (1996).
14. A. F. Burchat, D. J. Calderwood, M. M. Friedman, G. C. Hirst, B.-Q. LI, P. Rafferty, K. Ritter, and B. S. Skinner, Bioorg. & Med. Chem. Lett., 12, 1687-1690 (2002).
15. A. Miyashita, C. Iijima, and T. Higashino, Heterocycles, 31, 1309-1315 (1990).
16. Y. Tominaga, Y. Honkawa, M. Hara, and A. Hasomi, J. Heterocyclic Chem., 27, 775-783 (1990).
17. K. H. Reddy, A. P. Reddy, and U. Veeranagaiah, Indian J. Chem., Sect B: Organic Chemistry Including Medicinal Chemistry, 31(3), 163-166 (1992).
18. A. M. Farag and K. M. Dawood, Heteroatom. Chem., 8(1), 45-50 (1997).
19. V. J. Ram and N. Haque, Indian J. Chem., Sect B: Organic Chemistry including Medicinal Chemistry, 34(6), 521-524 (1995).
20. S. Guccione, L. Monsu Scolaro, and F. Russo, J. Heterocyclic Chem., 33(2), 459-463 (1996).
21. U. S. Pathak, S. Gandhi, and I. S. Rathod, Indian J. Chem., Sect B: Organic Chemistry Including Medicinal Chemistry, 33, 734-737 (1994).
22. E. C. Taylor, and M. Patel, J. Heterocyclic Chem., 28, 1857-1861 (1991).
23. M.-W. Ding, G.-P. Zeng, and T.-J. Wu, Syn. Commun., 30(9), 1599-1604 (2000).
24. M.-W. Ding, Zh.-F. Xu, and T.-J. Wu, Syn. Commun., 29(7), 1171-1176 (1999).
25. M.-W. Ding, G.-P. Zeng, and Zh.-J. Liu, Phosphorus Sulfur Silicon, 177, 1315-1321 (2002).
26. Y. Sasada, Molecular and Crystal Structure in Chemistry Handbook, 3rd ed. (The Chemical Society of Japan, Maruzen, Tokyo, 1984).
27. W.-Q. Chen and G.-Y. Jin, Phosphorus Sulfur Silicon, 177, 1193-1200 (2002).
28. J. Wilamowski, E. Kulig, J. J. Sepiol, and Z. J. Burgiel, Pest Manag. Sci., 57, 625-632 (2001).
29. W.-G. Zhao, Y.-B. Cao, Z.-M. Li, F.-W. Gao, S.-H. Wang, and J.-G. Wang, Chinese J. Appl. Chem., 18(60), 423-427 (2000).
30. H. Wamhoff, C. Bamberg, S. Herrmann, and M. Nieger, J. Org. Chem., 59, 3985-3993 (1994).