Interaction of β-lactam carbenes with 3,6-diphenyltetrazines: A five-step cascade reaction for the direct construction of indeno[2,1-b]pyrrol-2- ones

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4746-4752

  Xing, Juan ^a   Wang, Xiao Rong ^a   Yan, Cai Xia ^a   Cheng, Ying ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBENES; CASCADE PROCESS; CASCADE REACTIONS; EFFICIENT CONSTRUCTION; GOOD YIELD; NUCLEOPHILIC ADDITIONS; NUCLEOPHILICITIES; ONE POT; PYRAZOLE DERIVATIVES; TETRAZINES;

ADDITION REACTIONS;

ORGANIC COMPOUNDS;

CARBENE; PYRAZOLE DERIVATIVE; PYRROLE DERIVATIVE; TETRAZINE DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; NUCLEOPHILICITY; SYNTHESIS;

EID: 79957850852     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200499u     Document Type: Article

References (41)

1. Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606-5655
2. Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187
3. Bourissou, D.; Guerret, O.; Gabbai, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91
4. Cheng, Y.; Meth-Cohn, O. Chem. Rev. 2004, 104, 2507-2530
5. Some examples: Rigby, J. H.; Wang, Z. Org. Lett. 2002, 4, 4289-4291
6. Rigby, J. H.; Cavezza, A.; Ahmed, G. J. Am. Chem. Soc. 1996, 118, 12848-12849
7. Rigby, J. H.; Laurent, S. J. Org. Chem. 1999, 64, 1766-1767
8. Some examples: Couture, P.; Terlouw, J. K.; Warkentin, J. J. Am. Chem. Soc. 1996, 118, 4214-4215
9. Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1281-1294
10. El-Saidi, M.; Kassam, K.; Pole, D. L.; Tadey, T.; Warkentin, J. J. Am. Chem. Soc. 1992, 114, 8751-8752
11. Rigby, J. H.; Wang, Z. Org. Lett. 2003, 5, 263-264
12. Colomvakos, J. D.; Egle, I.; Ma, J.; Pole, D. L.; Tidwell, T. T.; Warkentin, J. J. Org. Chem. 1996, 61, 9522-9527
13. Some examples: Cheng, Y.; Wang, B.; Wang, X.-R.; Zhang, J.-H.; Fang, D.-C. J. Org. Chem. 2009, 74, 2357-2367
14. Cheng, Y.; Peng, J.-H.; Li, J.-Q. J. Org. Chem. 2010, 75, 2382-2388
15. Cheng, Y.; Liu, M.-F.; Fang, D.-C.; Lei, X.-M. Chem.-Eur. J. 2007, 13, 4282-4292
16. Li, J.-Q.; Liao, R.-Z.; Ding, W.-J.; Cheng, Y. J. Org. Chem. 2007, 72, 6266-6269
17. Ma, Y.-G.; Cheng, Y. Chem. Commun. 2007, 5087-5089
18. Some examples: Nair, V.; Sreekumar, V.; Bindu, S.; Suresh, E. Org. Lett. 2005, 7, 2297-2300
19. Nair, V.; Bindu, S.; Sreekumar, V.; Chiaroni, A. Org. Lett. 2002, 4, 2821-2823
20. Nair, V.; Bindu, S.; Sreekumar, V.; Rath, N. P. Org. Lett. 2003, 5, 665-667
21. Nair, V.; Deepthi, A.; Poonoth, M.; Santhamma, B. J. Org. Chem. 2006, 71, 2313-2319
22. Ma, C.; Ding, H.; Wu, G.; Yang, Y. J. Org. Chem. 2005, 70, 8919-8923
23. Ma, C.; Yang, Y. Org. Lett. 2005, 7, 1343-1345
24. Ma, C.; Ding, H.; Zhang, Y.; Bian, M. Angew. Chem., Int. Ed. 2006, 45, 7793-7797
25. Ding, H.; Zhang, Y.; Bian, M.; Yao, W.; Ma, C. J. Org. Chem. 2008, 73, 578-584
26. Kümmell, A.; Seitz, G. Tetrahedron Lett. 1991, 32, 2743-2746
27. Frenzen, G.; Kümmell, A.; Meyer-Dulheuer, C.; Seitz, G. Chem. Ber. 1994, 127, 1803-1806
28. Gerninghaus, C.; Kümmell, A.; Seitz, G. Chem. Ber. 1993, 126, 733-738
29. Imming, P.; Kümmell, A.; Seitz, G. Heterocycles. 1993, 35, 299-304
30. Bostai, B.; Novak, Z.; Benyei, A. C.; Kotschy, A. Org. Lett. 2007, 9, 3437-3439
31. Pan, H.-R.; Li, Y.-J.; Yan, C.-X.; Xing, J.; Cheng, Y. J. Org. Chem. 2010, 75, 6644-6652
32. Cheng, Y.; Ma, Y.-G.; Wang, X.-R.; Mo, J.-M. J. Org. Chem. 2009, 74, 850-855
33. Cheng, Y.; Zhu, Q.; Li, Q.-S.; Meth-Cohn, O. J. Org. Chem. 2005, 70, 4840-4846
34. Cheng, Y.; Yang, H.; Meth-Cohn, O. Chem. Commun. 2003, 90-91
35. Cheng, Y.; Cheng, L.-Q. J. Org. Chem. 2007, 72, 2625-2630
36. Cheng, Y.; Wang, B.; Cheng, L.-Q. J. Org. Chem. 2006, 71, 4418-4427
37. Zoghbi, M.; Warkentin, J. J. Org. Chem. 1991, 56, 3214-3215
38. Zoghbi, M.; Warkentin, J. Can. J. Chem. 1993, 71, 912-918
39. Fu, X.; Chen, J.; Li, G.; Liu, Y. Angew. Chem., Int. Ed. 2009, 48, 5500-5504
40. Azizian, J.; Karimi, A. R.; Arefrad, H.; Mohammadi, A. A.; Mohammadizadeh, M. R. Mol. Div. 2003, 6, 223-226
41. Geies, A. A. Pol. J. Chem. 1997, 71, 774-778