Synthesis of spirooxindolo/spiroindano nitro pyrrolizidines through regioselective azomethine ylide cycloaddition reaction

Synthetic Communications

Volumn 37, Issue 15, 2007, Pages 2507-2517

  Poornachandran, Mahalingam ^a   Raghunathan, Ragavachary ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Azomethine; Cycloaddition; Oxindole; Pyrrolizidine; Ylide

Indexed keywords

AZOMETHINE YLIDE; ISATIN; NINHYDRIN; PROLINE; PYRROLIZIDINE DERIVATIVE; SPIRO[2.2']INDAN 1',3' DIONE 3 (2 CHLORO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.2']INDAN 1',3' DIONE 3 (3 NITRO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.2']INDAN 1',3' DIONE 3 (4 CHLORO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.2']INDAN 1',3' DIONE 3 (4 METHOXY)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.2']INDAN 1',3' DIONE 3 (4 METHYL)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.2']INDAN 1',3' DIONE 3 PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 (2 CHLORO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 (3 NITRO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 (4 CHLORO)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 (4 METHOXY)PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 (4 METHYL}PHENYL 4 NITROPYRROLIZIDINE; SPIRO[2.3']OXINDOLO 3 PHENYL 4 NITROPYRROLIZIDINE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG SYNTHESIS;

EID: 34547866117     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701462575     Document Type: Article

References (26)

1. (a) Daly, J. W.; Spande, T. W. F.; Whittaker, N.; Highet, R. J.; Feigl, D.; Nishimori, T.; Tokuyama, T.; Myers, C. W. J. Nat. Prod. 1986, 49, 265-280;
2. (b) Hartmann, T.; Witte, L. Chemistry, biology and chemoecology of the pyrrolizidine alkaloids. In Alkaloids: Chemical and Biological Perspectives; Pelletier, (ed.); Pergamon Press: Oxford, UK, 1995; Vol. 9;
3. (c) Liddel, J. R. Nat. Prod. Rep. 1996, 13, 187 and 653.
4. Padwa, A. Comprehensive Organic Synthesis; Trost, I., Fleming, B. M., (Eds.); Pergamon: Oxford, 1991; Vol. 4, p. 1085.
5. Nájera, C.; Sansano, J. M. Current Organic Chemistry 2003, 7, 1105-1150.
6. (a) Longeon, A.; Guyot, M.; Vacelet, J. Experentia 1990, 46;
7. (b) Kobayashi, J.; Touda, M.; Agemi, K.; Shegemori, H.; Ishibashi, M.; Saski, T.; Mikami, Y. Tetrahedron 1991, 47, 6617;
8. (c) James, D. M.; Kunze, H. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1137;
9. (d) Waldmann, H. Synlett 1995, 133.
10. Sridhar, S. K.; Ramesh, A. Ind. J. Chem. 2002, 41B, 668-672.
11. Hilton, S. T.; Ho, T. C.; Pljevaljcic, G.; Jones, K. Org. Lett. 2000, 2, 2639.
12. (a) Okita, T.; Isobe, M. Tedrahedron 1994, 50, 11143;
13. (b) Rosenmund, P.; Hosseini-Merescht, M.; Bub, C. Liebigs Ann. Chem. 1994, 2, 151;
14. (c) Kornet, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892.
15. Kabat, H. Pharmocology, 1994, 80, 160.
16. (a) Nyerges, M.; Balázs, L.; Kádas, I.; Bitter, I.; Kövesdi, I.; Toke, L. Tetrahedron 1995, 51, 6783;
17. (b) Nyerges, M.; Rudas, M.; Toth, G.; Herenyi, B.; Kádas, I.; Bitter, I.; Toke, L. Tetrahedron 1995, 51, 13321.
18. (a) Ayerbe, M.; Cossío, F. P. Tetrahedron Lett. 1995, 36, 4447;
19. (b) Ayerbe, M.; Morao, I.; Arrieta, A.; Linden, A.; Cossío, F. P. Tetrahedron Lett. 1996, 37, 2311;
20. (c) Ayerbe, M.; Arrieta, A.; Cossío, F. P.; Linden, A. J. Org. Chem. 1998, 63, 1795.
21. Poornachandran, M.; Muruganantham, R.; Raghunathan, R. Synth. Commun. 2006, 36, 141-150.
22. (a) Amal Raj, A.; Raghunathan, R. Synth. Commun. 2002, 32, 3295-3300;
23. (b) Amal Raj, A.; Raghunathan, R. Synth. Commun. 2003, 33, 421-426;
24. (c) Amal Raj, A.; Raghunathan, R.; Sridevikumari, M. R.; Raman, N. Bioorg. Med. Chem. 2003, 11, 407-419.
25. Usha, G.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Poornachandran, M. Acta Cryst. 2005, E61, 03312-03314.
26. Usha, G.; Selvanayagam, S.; Velmurugan, D.; Ravikumar, K.; Raghunathan, R. Acta Cryst. 2005, E61, 03312-03314.