A polymer-assisted solution-phase strategy for the synthesis of fused [2,1-b]quinazolinones and the preparation of optically active vasicinone

Synlett

Volumn , Issue 16, 2006, Pages 2609-2612

  Kamal, Ahmed ^a   Devaiah, V ^a   Shankaraiah, N ^a   Laxma Reddy, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Fused 2,1 b quinazolinones; Oxidations; Polymer supported reagents; Vasicinone

Indexed keywords

4 VINYLPYRIDINIUMCHROMATE; [2,1 B]QUINAZOLINE DERIVATIVE; ADHATODA VASICA EXTRACT; ALKALOID; PLANT EXTRACT; POLYMER; PYRIDINIUM DERIVATIVE; PYRROLO[2,1 B]QUINAZOLINE 3,9 DIONE; QUINAZOLINE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG; VASCICINONE;

ADHATODA; ARTICLE; CHEMICAL STRUCTURE; OPTICS; OXIDATION; REDUCTION; SYNTHESIS; TECHNIQUE;

EID: 33750052931     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951482     Document Type: Article

References (44)

1. For recent reviews, see: (a) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem. Int. Ed. 2001, 40, 650.
2. (b) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815.
3. (c) Storer, R. I.; Takemoto, T.; Jackson, P. S.; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 2521.
4. (d) Jaunzems, J.; Hofer, E.; Jesberger, M.; Sourkouni-Argirusi, G.; Kirschning, A. Angew. Chem. Int. Ed. 2003, 42, 1166.
5. (e) Storer, P. I.; Takemoto, T.; Jackson, P. S.; Brown, D. S.; Baxendale, I. R.; Ley, S. V. Chem. Eur. J. 2004, 10, 2529.
6. (f) Wang, Y.; Sauer, D. R. Org. Lett. 2004, 6, 2793.
7. (g) Siu, J.; Baxendale, I. R.; Lewthwaite, R. A.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 3140.
8. (a) Johne, S.; Groger, D. Pharmazie 1970, 25, 22.
9. (b) Coppola, M. Synthesis 1980, 505.
10. (c) Johne, S. Prog. Drug Res. 1982, 26, 259.
11. (d) Johne, S. Prog. Chem. Org. Nat. Prod. 1984, 46, 159.
12. (e) Michael, J. P. Nat. Prod Rep. 2000, 17, 603; and references cited therein.
13. (a) Amin, A. H.; Mehta, D. R. Nature 1959, 183, 1317.
14. (b) Mehta, D. R.; Naravane, J. S.; Desai, R. M. J. Org. Chem. 1963, 28, 445.
15. (c) Jain, M. P.; Koul, S. K.; Dhar, K. L.; Atal, C. K. Phytochemistry 1980, 19, 1880.
16. (a) Kamal, A.; Ramana, K. V.; Rao, M. V. J. Org. Chem. 2001, 66, 997.
17. (b) Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2001, 66, 9098.
18. (c) Kamal, A.; Ramana, A. V.; Reddy, K. S.; Ramana, K. V.; Babu, A. H.; Prasad, B. R. Tetrahedron Lett. 2004, 45, 8187.
19. (a) Al-Shamma, A.; Drake, S.; Flynn, D. L.; Mitscher, L. A.; Park, Y. H.; Rao, G. S. R.; Simpson, A.; Swayze, J. K.; Veysoglu, T.; Wu, S. T. S. J. Nat. Prod. 1981, 44, 745.
20. (b) Koizumi, M.; Matsuura, I.; Murakami, Y. Japan Kokai 7,777,093,1977; Chem. Abstr. 1978, 88, 6930.
21. (a) Duan, J.; Zhou, R.; Zhao, S.; Wang, M.; Che, C. Zhongguo Yaoke Daxue Xuebao 1998, 29, 21.
22. (b) Fan, Z.; Yao, X.; Gu, L.; Wang, J.; Wang, J.; He, A.; Zhang, B.; Wang, X.; Wang, H. Shenyang Yaoxueyuan Xuebao 1993, 10, 136.
23. (c) Rahman, A. U.; Sultana, N.; Akhter, F.; Nighat, F.; Choudhary, M. I. Nat. Prod. Lett. 1997, 10, 249.
24. (d) D'Cruz, J. L.; Nimbkar, A. Y.; Kokate, C. K. Indian Drugs 1980, 17, 99.
25. (e) Bhide, M. B.; Mahajani, S. S. Bull. Haffkine Inst. 1975, 3, 128.
26. (f) Choudhury, M. K. Naturwissenschaften 1979, 66, 205.
27. (a) Kamal, A.; Reddy, K. L.; Devaiah, V.; Shankaraiah, N. Synlett 2004, 2533.
28. (b) Kamal, A.; Devaiah, V.; Reddy, K. L.; Shankaraiah, N. Adv. Synth. Catal. 2006, 348, 249.
29. (a) Weinshenker, N. M.; Shen, C. M.; Wong, J. Y. Org. Synth., Coll. Vol. VI; John Wiley & Sons: London, 1988, 951.
30. (b) Wolman, Y.; Kivity, S.; Frankel, M. J. Chem. Soc., Chem. Commun. 1967, 629.
31. (c) Grieder, A.; Thomas, A. W. Synthesis 2003, 1707.
32. (d) Ploypradith, P.; Kagan, R. K.; Ruchirawat, S. J. Org. Chem. 2005, 70, 5119.
33. (e) Choi, J.; Yoon, N. M. Synth. Commun. 1995, 25, 2655.
34. (f) Frechet, J. M. J.; Darling, P.; Farrall, M. J. J. Org. Chem. 1981, 46, 1728.
35. (g) Hu, J.-B.; Zhao, G.; Ding, Z.-D. Angew. Chem. Int. Ed. 2001, 40, 1109.
36. +].
37. +].
38. +].
39. +].
40. +].
41. +].
42. Conditions: Chiracel OD column employing hexane-2-propanol (85:15) as the mobile phase at 0.7 mL/min flow rate and monitored at 254 nm wavelength.
43. (a) Rajlakshmi, P.; Aditya, N. C. J. Ind. Chem. Soc. 1988, 65, 814.
44. (b) Mehta, D. R.; Naravane, J. S.; Desai, R. M. J. Org. Chem. 1963, 28, 445.