An efficient route to tetrahydroindeno[2,1-b]pyrroles via a base-promoted reaction of (E)-2-alkynylphenylchalcone with 2-isocyanoacetate

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6402-6405

  Zheng, Danqing ^a   Li, Shaoyu ^a   Luo, Yong ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKYNE; CHALCONE DERIVATIVE; FUSED HETEROCYCLIC RINGS; INDENE DERIVATIVE; NITRILE; PYRROLE DERIVATIVE;

AIR; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ACETATES; AIR; ALKYNES; CATALYSIS; CHALCONES; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS, 3-RING; INDENES; MOLECULAR STRUCTURE; NITRILES; PYRROLES;

EID: 84055214053     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202708f     Document Type: Article

References (46)

1. (a) Walsh, D. P.; Chang, Y.-T. Chem. Rev. 2006, 106, 2476.
2. (b) Arya, P.; Chou, D. T. H.; Baek, M.-G. Angew. Chem., Int. Ed. 2001, 40, 339.
3. (c) Schreiber, S. L. Science 2000, 287, 1964.
4. (d) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
5. (e) Schreiber, S. L. Nature 2009, 457, 153.
6. (f) Tan, D. S. Nat. Chem. Biol. 2005, 1, 74.
7. (g) Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; O'Leary-Steele, C. Nat. Prod. Rep. 2008, 25, 719.
8. For reviews, see: (a) Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890.
9. (b) Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Liu, F. Chem. Rev. 1996, 96, 365.
10. (c) Tietze, L. F. Chem. Rev. 1996, 96, 115.
11. (d) Grigg, R.; Sridharan, V. J. Organomet. Chem. 1999, 576, 65.
12. (e) Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
13. (f) Malacria, M. Chem. Rev. 1996, 96, 289.
14. (g) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
15. (h) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
16. (i) Enders, D.; Grondal, C.;Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
17. (j) Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis;Wiley- VCH: Weinheim, Germany, 2006.
18. For recent selected examples: (a) Lu, P.; Wang, Y.-G. Synlett 2010, 165.
19. (b) Yoo, E. J.; Chang, S. Curr. Org. Chem. 2009, 13, 1766.
20. (c) Zou, Y.-Q.; Lu, L.-Q.; Li, F.; Chang, N.-J.; Rong, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2011, 50, 7171.
21. (d) Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, DOI: 10.1021/ar2000343.
22. (e) Guo, L.-N.; Duan, X.-H.; Liang, Y.-M. Acc. Chem. Res. 2011, 44, 111.
23. (f) Feng, J.-J.; Zhang, J. J. Am. Chem. Soc. 2011, 133, 7304.
24. (a) Luo, Y.; Pan, X.; Wu, J. Org. Lett. 2011, 13, 1150.
25. (b) Luo, Y.; Hong, L.; Wu, J. Chem. Commun. 2011, 47, 5298.
26. (c) Pan, X.; Luo, Y.; Wu, J. Chem. Commun. 2011, 47, 8967.
27. (d) Luo, Y.; Wu, J. Chem. Commun. 2011, 47, 11137.
28. (e) Qiu, G.; Ding, Q.; Gao, K.; Peng, Y.; Wu, J. ACS Comb. Sci. 2011, 13, 13.
29. (f) Ye, S.; Yang, X.; Wu, J. Chem. Commun. 2010, 46, 2950.
30. (g) Ye, S.; Ren, H.; Wu, J. J. Comb. Chem. 2010, 12, 670.
31. (h) Qiu, G.; Ding, Q.; Peng, Y.; Wu, J. Tetrahedron Lett. 2010, 51, 4391.
32. (i) Ye, S.; Gao, K.; Zhou, H.; Yang, X.; Wu, J. Chem. Commun. 2009, 5406.
33. (j) Gao, K.; Wu, J. Org. Lett. 2008, 10, 2251.
34. For reviews: (a) Suginome, M.; Ito, Y. In Science of Synthesis,Vol. 19; Murahashi, S.-I., Ed.; Thieme: Stuttgart, 2004; p 445.
35. (b) Dömling, A. Chem. Rev. 2006, 106, 17.
36. (c)Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
37. (d) Lygin, A. V.; Meijere, A. D. Angew. Chem., Int. Ed. 2010, 49, 9094.
38. (e) Gulevich, A. V.; Zhdanko, A. G.; Orru, R. V. A.; Nenajdenko, V. G. Chem. Rev. 2010, 110, 5235.
39. For recent examples, see: (a) Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. Soc. 2011, 133, 1775.
40. (b) Zhou, H.; Zhang, W.; Yan, B. J. Comb. Chem. 2010, 12, 206.
41. (c) Monge, D.; Jensen, K. L.; Marn, I.; Jørgensen, K. A. Org. Lett. 2011, 13, 328.
42. Chen, Z.; Ye, C.; Gao, L.; Wu, J. Chem. Commun. 2011, 47, 5623.
43. For selected examples, see: (a) Johnson, C. D. Acc. Chem. Res. 1993, 26, 476.
44. (b) Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, dx.doi. org/10.1021/cr200164y.
45. (c) Park, J. H.; Bhilare, S. V.; Youn, S. W. Org. Lett. 2011, 13, 2228.
46. (d) Uchiyama, M.; Ozawa, H.; Takuma, K.; Matsumoto, Y.; Yonehara, M.; Hiroya, K.; Sakamoto, T. Org. Lett. 2006, 8, 5517.