Extension of the Biginelli-type reaction: One-pot synthesis of pyrimido-pyrimidines and spirobi[pyrimidine]s using potassium hydrogen sulfate as a catalyst

Synthesis

Volumn , Issue 18, 2007, Pages 2782-2790

  Shi, Feng ^a   Jia, Runhong ^a   Zhang, Xiaojing ^a   Tu, Shujiang ^a   Yan, Shu ^a   Zhang, Yan ^a   Jiang, Bo ^a   Zhang, Junyong ^a   Yao, Changsheng ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

Author keywords

Michael additions; Multicomponent reactions; Potassium hydrogen sulfate; Pyrimido 4,5 d pyrimidine; Spirobi hexahydropyrimidine

Indexed keywords

MICHAEL ADDITIONS; MULTICOMPONENT REACTIONS; POTASSIUM HYDROGEN SULFATE; PYRIMIDO[4,5-D]PYRIMIDINE; SPIROBI[HEXAHYDROPYRIMIDINE];

ADDITION REACTIONS; CATALYSTS; KETONES; POTASSIUM COMPOUNDS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

4,5,8A TRIARYLHEXAHYDROPYRIMIDO[4,5 D]PYRIMIDINE 2,7(1H,3H) DIONE DERIVATIVE; 6,6' DIARYL 4,4' SPIROBI[HEXAHYDROPYRIMIDINE] 2,2 DIONE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MICHAEL ADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

EID: 34948862764     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983874     Document Type: Article

References (32)

1. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
2. (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.
3. (b) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwart, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254.
4. (c) Grover, G. J.; Dzwonczyk, S.; Mcmullen, D. M.; Normadinam, C. S.; Slenph, P. G.; Moreland, S. J. J. Cardiovasc. Pharmacol. 1995, 26, 289.
5. (a) Huang, Y. J.; Yang, F. Y.; Zhu, C. J. J. Am. Chem. Soc. 2005, 127, 16386.
6. (b) Tu, S. J.; Fang, F.; Miao, C. B.; Jiang, H.; Feng, Y. J.; Shi, D. Q.; Wang, X. S. Tetrahedron Lett. 2003, 44, 6153.
7. (c) Tu, S. J.; Fang, F.; Zhu, S. L.; Li, T. J.; Zhang, X. J.; Zhuang, Q. Y. Syhlett 2004, 537.
8. (d) Kappe, C. O.; Falsone, S. F. Synlett 1998, 718.
9. (e) Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075.
10. (f) Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63, 3454.
11. (g) Ramalinga, K.; Vijayalaxmi, P.; Kaimal, T. N. B. Synlett 2001, 863.
12. (h) Kumar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C. D. Tetrahedron Lett. 2001, 42, 7873.
13. Zhu, Y. L.; Huang, S. L.; Pan, Y. J. Eur. J. Org. Chem. 2005, 2354.
14. (a) Sedova, V. F.; Shkurko, O. P. Chem. Heterocycl. Compd. (Engl. Transl.) 2004, 40, 194.
15. (b) Sedova, V. F.; Baranova, L. V.; Mamaev, V. P. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim, Nauk 1972, 6, 96.
16. (c) Sedova, V. F.; Mamaev, V. P. Khim. Geterotsikl. Soed. 1970, 5, 691.
17. (a) Lunt, E. Comprehensive Organic Chemistry, Vol. 4; Barton, D.; Ollis, W. D., Eds.; Pergamon: Oxford, 1974, 493.
18. (b) Brown, J. D. Comprehensive Heterocyclic Chemistry, Vol. 3; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 57.
19. (c) Clercq, E. D.; Beraaerts, R. J. Biol. Chem. 1987, 262, 14905.
20. Coates, W. J. EP 351,058, 1990; Chem. Abstr. 1990, 113, 40711.
21. Kitamura, N.; Onishi, A. EP 163,599, 1984; Chem. Abstr. 1984, 104, 186439.
22. Raddatz P., Bergmann R., Ger. Pat. 3601731, 1988; Chem. Abstr. 1988, 109, 54786.
23. Delia, T. J.; Baumann, M.; Bunker, A. Heterocycles 1993, 35, 1397.
24. (a) Hirota, K.; Kitade, Y.; Senda, S.; Halat, M. J.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1981, 46, 846.
25. (b) Su, T. L.; Huang, J. T.; Burchanal, J. H.; Watanabe, K. A.; Fox, J. J. J. Med. Chem. 1986, 29, 709.
26. (c) Prajapati, D.; Sandhu, J. S. Synthesis 1988, 342.
27. -3.
28. (a) Sedova, V. F.; Mamaev, V. M. Khim. Geterotsikl. Soed. 1968, 5, 921.
29. (b) Zigeuner, G.; Brunetti, H.; Ziegler, H.; Bayer, M. Monatsh. Chem. 1970, 101, 1767.
30. (c) Hatt, H. H. Aust. J. Chem. 1970, 23, 577.
31. (d) Sedova, V. F.; Baranova, L. V.; Mamaev, V. P. Ser. Khim. Nauk 1972, 6, 96.
32. (e) Sedova, V. F.; Mamaev, V. P. Khim. Geterotsikl. Soed. 1970, 5, 691.