Intramolecular cycloaddition of azomethine ylides in the preparation of pyrrolidino[2′,3′:3,4]pyrrolidino[1,2-a]benzimidazoles

Organic Letters

Volumn 9, Issue 24, 2007, Pages 5055-5058

  Meng, Liping ^a,b   Fettinger, James C ^a   Kurth, Mark J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; AZOMETHINE; BENZIMIDAZOLE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; BENZIMIDAZOLES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; THIOSEMICARBAZONES;

EID: 36849090099     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702301n     Document Type: Article

References (27)

1. (1 )Soutnon, I. W.; Buckingham, J., Eds. Dictionary of Alkaloids; Chapman & Hall: New York, 1989.
2. (a) Li, Q.; Chu, D. T. W.; Claiborne, A.; Copper, C. S.; Lee, C. M.; Raye, K.; Berst, K. B.; Donner, P.; Wang, W.; Hasvold, L.; Fung, A.; Ma, Z.; Tufano, M.; Flamm, R.; Shen, L. L.; Baranowski, J.; Nilius, A.; Alder, J.; Meulbroek, J.; Marsh, K.; Crowell, D. A.; Hui, Y.; Seif, L.; Melcher, L. M.; Henry, R.; Spanton, S.; Faghih, R.; Klein, L. L.; Tanaka, S. K.; Plattner, J. J. J. Med. Chem. 1996, 39, 3070.
3. (b) Hamilton, G. S.; Steiner, J. P. Curr. Pharm. Des. 1997, 3, 405.
4. (c) Yaron, A.; Naider, F. Curr. Rev. Biochem. Mol. Biol. 1993, 25, 31.
5. (a) Broggini, G.; Zecchi, G. Synthesis 1999, 6, 905.
6. (b) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
7. (a) Najdi, S.; Park, K. H.; Olmstead, M. M.; Kurth, M. J. Tetrahedron Lett. 1998, 39, 1685.
8. (b) Gong, Y. D.; Kurth, M. J. Tetrahedron Lett. 1998, 39, 3379.
9. (c) Gong, Y. D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081.
10. Nagashima, H.; Inoue, H.; Yoshioka, N. J. Phys. Chem. 2004, 108, 6144.
11. (a) Bashiardes, G.; Safir, I.; Mohamed, A. S.; Barbot, F.; Laduranty, J. Org. Lett. 2003, 5, 4915.
12. (b) Neuschl, M.; Bogdal, D.; Potacek, M. Molecules 2007, 12, 49.
13. Pospisil, J.; Potacek, M. Eur. J. Org. Chem. 2004, 710.
14. Dimer formation occurs when the azomethine ylide undergoes an intermolecular addition to its precursor aldehyde to form 3-(substituted)- oxazolidine-4-carboxylates as a complex mixture of regio- and stereoisomers. See: (a) Brome, V. A.; Harwood, L. M.; Osborn, H. M. I. Can. J. Chem. 2006, 84, 1448.
15. (b) Aldous, D. J.; Drew, M. G. B.; Draffin, W. N.; Hamelin, E. M.-N.; Harwood, L. M.; Thurairatnam, S. Synthesis 2005, 3271.
16. (C) Travnicek, M.; Potacek, M. ARKIVOC (Gainesville, FL, U.S.) 2001, 156.
17. (d) Rudas, M.; Fejes, I.; Nyerges, M.; Szollosy, A.; Toke, L.; Groundwater, P. W. J. Chem. Soc., Perkin Trans. 1 1999, 1167.
18. (e) Felluga, F.; Pitacco, G.; Visintin, C.; Valentin, E. Helv. Chim. Acta 1997, 80, 1457.
19. (f) Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960.
20. (a) Snider, B. B.; Ahn, Y.; O'Hare, S. M. Org. Lett. 2001, 3, 4217.
21. (b) Pedrosa, R.; Andres, C; Heras, L. D. L.; Nieto, J. Org. Lett. 2002, 4, 2513.
22. (c) Pedrosa, R.; Andres, C.; Nieto, J.; Perez-Cuadrado, C.; Francisco, I. S. Eur. J. Org. Chem. 2006, 3259.
23. (d) Garner, P.; Kaniskan, H. U. Tetrahedron Lett. 2005, 46, 5181.
24. (e) Poornachandran, M.; Raghunathan, R. Tetrahedron Lett. 2005, 46, 7197.
25. (f) Yang, X.; Luo, S.; Fang, F.; Liu, P.; Lu, Y.; He, M.; Zhai, H. Tetrahedron 2006, 62, 2240.
26. Crystal structures have been deposited at the Cambridge Crystallographic Data Centre and allocated the following deposition numbers: CCDC 661436 for 5aA and CCDC 661435 for 7aA{l}.
27. Hoegberg, T.; Stroem, P.; Ebner, M.; Raemsby, S. J. Org. Chem. 1987, 52, 2033.