NH 4OAc promoted cyclocondensation of 3-(o-allylphenyl)pentane-1, 5-diones: Synthesis of tetracyclic benzofused 1-azahomoisotwistanes

Organic Letters

Volumn 14, Issue 15, 2012, Pages 3936-3939

  Chang, Meng Yang ^a   Wu, Ming Hao ^a   Tai, Hang Yi ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; AMMONIUM ACETATE; AZABICYCLO DERIVATIVE; FUSED HETEROCYCLIC RINGS; KETONE; PENTANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ACETATES; AZABICYCLO COMPOUNDS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; KETONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PENTANES;

EID: 84864615901     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301693s     Document Type: Article

References (41)

1. Kharchenko, V. G.; Markova, L. I.; Fedotova, O. V.; Pchelintseva, N. V. Chem. Heterocycl. Compd. 2003, 39, 1121
2. Hill, M. D. Chem.-Eur. J. 2010, 16, 12052
3. Henry, G. D. Tetrahedron 2004, 60, 6043
4. Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787
5. Heller, B.; Hapke, M. Chem. Soc. Rev. 2007, 36, 1085
6. Dey, A.; Pal, C.; Nandi, D.; Giri, V. S.; Zaidlewicz, M.; Krzeminski, M.; Smentek, L.; Hess, B. A., Jr.; Gawronski, J.; Kwit, M.; Bahu, N. J.; Nangia, A.; Jaisankar, P. Org. Lett. 2008, 10, 1373
7. Fatemeh, T.; Mahnaz, F. Synlett 2012, 1379
8. Davis, F. A.; Edupuganti, R. Org. Lett. 2010, 12, 848
9. Sasada, T.; Kobayashi, F.; Sakai, N.; Konakahara, T. Org. Lett. 2009, 11, 2161
10. Wolkenberg, S. E.; Wisnoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453
11. Wang, J.; Dyers, L.; Mason, R., Jr.; Amoyaw, P.; Bu, X. R. J. Org. Chem. 2005, 70, 2353
12. Kundu, N.; Bhattacharya, K.; Abtab, S. M. T.; Chaudhury, M. Tetrahedron Lett. 2012, 53, 2719
13. Hosseini-Zare, M. S.; Mahdavi, M.; Saeedi, M.; Asadi, M.; Javanshir, S.; Shafiee, A.; Foroumadi, A. Tetrahedron Lett. 2012, 53, 3448
14. Khalili, B.; Tondro, T.; Hashemi, M. M. Tetrahedron 2009, 65, 6882
15. Kelly, T. R.; Lebedev, R. L. J. Org. Chem. 2002, 67, 2197
16. Donohoe, T. J.; Basutto, J. A.; Bower, J. F.; Rathi, A. Org. Lett. 2011, 13, 1036
17. Hu, J.; Zhang, Q.; Yuan, H.; Liu, Q. J. Org. Chem. 2008, 73, 2442
18. Thapa, P.; Karki, R.; Yun, M.; Kadayat, T. M.; Lee, E.; Kwon, H. B.; Na, Y.; Cho, W.-J.; Kim, N. D.; Jeong, B.-S.; Kwon, Y.; Lee, E.-S. Eur. J. Med. Chem. 2012, 52, 123
19. Craig, D.; Henry, G. D. Tetrahedron Lett. 2005, 46, 2559
20. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Essawy, S. A. Synthesis 1999, 2114
21. Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459
22. Aulakh, V. S.; Ciufolini, M. A. J. Org. Chem. 2009, 74, 5750
23. Allais, C.; Constantieux, T.; Rodriguez, J. Chem.-Eur. J. 2009, 15, 12945
24. Wypych, J.-C.; Nguyen, T. M.; Benechie, M.; Marazano, C. J. Org. Chem. 2008, 73, 1169
25. Cave, G. W. V.; Raston, C. L. Chem. Commun. 2000, 2199
26. Tu, S.; Li, T.; Shi, F.; Fang, F.; Zhu, S.; Wei, X.; Zhong, Z. Chem. Lett. 2005, 34, 732
27. Adib, M.; Tahermansouri, H.; Koloogani, S. A.; Mohammadi, B.; Bijanzadeh, H. R. Tetrahedron Lett. 2006, 47, 5957
28. Wang, P.; Moorefield, C. N.; Newkome, G. R. Org. Lett. 2004, 6, 1197
29. Chang, M.-Y.; Wu, M.-H. Tetrahedron Lett. 2012, 53, 3173
30. Chang, M.-Y.; Wu, M.-H.; Lee, N.-C.; Lee, M.-F. Tetrahedron Lett. 2012, 53, 2125
31. Srikrishna, A.; Ravi., G. Tetrahedron 2008, 64, 2565
32. Srikrishna, A.; Satyanarayana, G. Tetrahedron: Asymmetry 2005, 16, 3992
33. Evan, D. A.; Golob, A. M.; Mandel, N. S.; Mandel, G. S. J. Am. Chem. Soc. 1978, 100, 8170
34. Takaishi, N.; Inamoto, Y.; Aigami, K. J. Org. Chem. 1980, 45, 2254
35. Kröhnke, F.; Zecher, W. Angew. Chem., Int. Ed. 1962, 1, 626
36. Yanagisawa, A.; Takahashi, H.; Arai, T. Tetrahedron 2007, 63, 8681
37. Waldmann, H.; Karunakar, G. V.; Kumar, K. Org. Lett. 2008, 10, 2159
38. Hartman, G. D.; Halczenko, W.; Phillips, B. T. J. Org. Chem. 1985, 50, 2427
39. Hartman, G. D.; Halczenko, W.; Phillips, B. T. J. Org. Chem. 1986, 51, 142
40. Margrey, K. A.; Chinn, A. J.; Laws, S. W.; Pike, R. D.; Scheerer, J. R. Org. Lett. 2012, 14, 2458
41. CCDC 883599 (2a), 883600 (2c), 887548 (2j), 887547 (2n), 883594 (4a), and 883595 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk).