Rapid photoassisted access to N,O,S-polyheterocycles with benzoazocine and hydroquinoline cores: Intramolecular cycloadditions of photogenerated azaxylylenes

Angewandte Chemie - International Edition

Volumn 50, Issue 40, 2011, Pages 9423-9428

  Mukhina, Olga A ^a   Bhuvan Kumar, N N ^a   Arisco, Teresa M ^a   Valiulin, Roman A ^a   Metzel, Greg A ^a   Kutateladze, Andrei G ^a  

^a UNIVERSITY OF DENVER   (United States)

Author keywords

cycloaddition; heterocycles; molecular diversity; o azaxylylenes; photochemistry

Indexed keywords

CYCLOADDITIONS; DIVERSITY-ORIENTED SYNTHESIS; HETEROCYCLES; HIGH-THROUGHPUT; INTRAMOLECULAR CYCLOADDITIONS; MOLECULAR DIVERSITY; O-AZAXYLYLENES; SYNTHETIC METHODS;

PHOTOCHEMICAL REACTIONS; SCAFFOLDS;

CYCLOADDITION;

AZOCINE DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROQUINONE; HYDROQUINONE DERIVATIVE; KETONE; NITROGEN; OXYGEN; PROLINE; SULFUR; THIAZOLIDINE DERIVATIVE; THIAZOLIDINE-4-CARBOXYLIC ACID; TIMONACIC;

ARTICLE; CHEMISTRY; CYCLIZATION; METHODOLOGY; ORGANIC CHEMISTRY; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZOCINES; CHEMISTRY, ORGANIC; CYCLIZATION; HETEROCYCLIC COMPOUNDS; HYDROQUINONES; KETONES; NITROGEN; OXYGEN; PHOTOCHEMISTRY; PROLINE; STEREOISOMERISM; SULFUR; THIAZOLIDINES;

EID: 80053145515     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103597     Document Type: Article

References (29)

1. G. Smolinsky, J. Org. Chem. 1961, 26, 4108; for the most recent review, see
2. K. Wojciechowski, Eur. J. Org. Chem. 2001, 3587.
3. H. Steinhagen, E. J. Corey, Angew. Chem. 1999, 111, 2054
4. Angew. Chem. Int. Ed. 1999, 38, 1928.
5. K. C. Nicolaou, D. L. F. Gray, J. Tae, J. Am. Chem. Soc. 2004, 126, 613
6. K. C. Nicolaou, D. L. F. Gray, J. Am. Chem. Soc. 2004, 126, 607
7. K. C. Nicolaou, D. Gray, Angew. Chem. 2001, 113, 783
8. Angew. Chem. Int. Ed. 2001, 40, 761
9. K. C. Nicolaou, D. L. F. Gray, J. Tae, Angew. Chem. 2001, 113, 3791
10. Angew. Chem. Int. Ed. 2001, 40, 3675
11. G. A. Kraus, Y. Wu, J. Org. Chem. 1992, 57, 2922
12. G. Quinkert, H. Stark, Angew. Chem. 1983, 95, 651
13. Angew. Chem. Int. Ed. Engl. 1983, 22, 637
14. S. Prabhakar, A. M. Lobo, M. R. Tavares, I. M. C. Oliveira, J. Chem. Soc. Perkin Trans. 1 1981, 1273
15. G. Quinkert, W.-D. Weber, U. Schwartz, G. Dürner, Angew. Chem. 1980, 92, 1060
16. Angew. Chem. Int. Ed. 1980, 19, 1027
17. G. Quinkert, U. Schwartz, H. Stark, W.-D. Weber, H. Baier, F. Adam, G. Dürner, Angew. Chem. 1980, 92, 1062
18. Angew. Chem. Int. Ed. 1980, 19, 1029
19. for review see, J. L. Segura, N. Martín, Chem. Rev. 1999, 99, 3199.
20. R. Haag, J. Wirz, P. J. Wagner, Helv. Chim. Acta 1977, 60, 2595.
21. See:, S. Schmidtke, D. F. Underwood, D. A. Blank, J. Phys. Chem. A 2005, 109, 7033, and references therein.
22. L. Lapinski, H. Rostkowska, I. Reva, R. Fausto, M. J. Nowak, J. Phys. Chem. A 2010, 114, 5588.
23. B. Xia, B. Gerard, D. M. Solano, J. Wan, G. Jones, J. A. Porco, Org. Lett. 2011, 13, 1346.
24. D. Song, R. McDonald, F. G. West, Org. Lett. 2006, 8, 4075
25. L. Li, J. A. Bender, F. G. West, Tetrahedron Lett. 2009, 50, 1188.
26. P. Chen, Y. Chen, P. J. Carroll, S. McN. Sieburth, Org. Lett. 2006, 8, 3367
27. P. Chen, P. J. Carroll, S. McN. Sieburth, Org. Lett. 2010, 12, 4510.
28. B. C. Gorske, J. R. Stringer, B. L. Bastian, S. A. Fowler, H. E. Blackwell, J. Am. Chem. Soc. 2009, 131, 16555; for a recent review see
29. S. A. Fowler, H. E. Blackwell, Org. Biomol. Chem. 2009, 7, 1508.