Synthesis of aza/oxaspiro-γ-lactams by radical translocation cyclization reactions

Synlett

Volumn , Issue 12, 2005, Pages 1865-1868

  Xu, Xianxiu ^a   Che, Xin ^a   Gao, Shu ^a   Wu, Jinchang ^a   Bai, Xu ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

1,5 hydrogen transfer; Radical translocation; Spiro lactams

Indexed keywords

AZA/OXASPIRO GAMMA LACTAM; BENZENE DERIVATIVE; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; GAMMA LACTAM DERIVATIVE; N ALLYL N (2' BROMOPHENYL)AMIDE; SPIRO GAMMA LACTAM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 23644456521     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871563     Document Type: Article

References (26)

1. For reviews see: (a) Westermann, B.; Diedrichs, N.; Gedrath, I.; Walter, A. Bioorg. Chem. 1999, 185.
2. (b) Hanessian, S.; McNaughton-Simth, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
3. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244.
4. (d) Alonso, E.; López-Ortiz, F.; Del Pozo, C.; Peralta, E.; Macías, A.; Gonzalez, J. J. Org. Chem. 2001, 66, 6333.
5. (e) Muller, G.; Hessler, G.; Decornez, H. Y. Angew. Chem. Int. Ed. 2000, 39, 894.
6. Genin, M. J.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 2334.
7. (a) Fernández, M. M.; Diez, A.; Rubiralta, M.; Montenegro, E.; Casamitjana, N. J. Org. Chem. 2002, 67, 7587.
8. (b) Genin, M. J.; Gleason, W. B.; Johnson, R. L. J. Org. Chem. 1993, 58, 860.
9. Braña, M. F.; Garranzo, M.; Pascual, T. B.; Pérez-Castells, J.; Torres, M. R. Tetrahedron 2002, 58, 4825.
10. (a) Ganguly, A. K.; Seah, N.; Popv, V.; Wang, C. H.; Kuang, R.; Saksena, A. K.; Pramanik, B. N.; Chan, T. M.; McPhail, A. T. Tetrahedron Lett. 2002, 43, 8981.
11. (b) Nair, V.; Rajesh, C.; Dhanya, R.; Rath, N. P. Tetrahedron Lett. 2002, 43, 5349.
12. (c) Nair, V.; Sheela, K. C.; Rath, N. P. Chem. Lett. 2000, 9, 980.
13. For a review see: (a) Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94
14. . For typical examples see: (b) Storey, J. M. D. Tetrahedron Lett. 2000, 41, 8173.
15. (c) Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 115, 6051.
16. (d) Beaulieu, F.; Arora, J.; Veith, U.; Taylor, N. J.; Chapell, B. J.; Snieckus, V. J. Am. Chem. Soc. 1996, 118, 8727.
17. (e) Curran, D. P.; Xu, J. J. Am. Chem. Soc. 1996, 118, 3142.
18. (f) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343.
19. (g) Curran, D. P.; Liu, H. T. J. Chem. Soc., Perkin Trans. 1 1994, 1377.
20. (h) Curran, D. P.; Kim, D.; Liu, H.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900.
21. (i) Beaufils, F.; Dénès, F.; Renaud, P. Org. Lett. 2004, 6, 2563.
22. (a) Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438.
23. (b) Takasu, K.; Ohsato, H.; Ihara, M. Org. Lett. 2003, 5, 3017.
24. (c) Hilton, S. T.; Ho, T. C. T.; Pljevaljcic, G.; Schulte, M.; Jones, K. Chem. Commun. 2001, 209.
25. +].
26. 4, and concentrated in vacuo to give 13f (113 mg, 87%) as a light yellowish solid (mp 82.1-84.0°C).