Regioselective ring expansion of 2,4-diiminoazetidines via cleavage of C-N and C(sp 3)-H bonds: Efficient construction of 2,3- dihydropyrimidinesulfonamides

Journal of the American Chemical Society

Volumn 134, Issue 6, 2012, Pages 2926-2929

  Wang, Yang ^a   Chi, Yue ^a   Zhang, Wen Xiong ^a,b   Xi, Zhenfeng ^a  

^a PEKING UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM LABELING; EFFICIENT CONSTRUCTION; H-BONDS; REGIO-SELECTIVE; REGIOSELECTIVE RING; RING CLOSINGS; RING EXPANSION; RING OPENING;

DEUTERIUM; REGIOSELECTIVITY;

EXPANSION;

AZETIDINE DERIVATIVE; DEUTERIUM; IMINE; PYRIMIDINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY;

AZETIDINES; CARBON; CHEMISTRY; CYCLIZATION; ELECTRONS; HYDROGEN; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; NITROGEN; STEREOISOMERISM; SULFONAMIDES;

EID: 84863161901     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211486f     Document Type: Article

References (64)

1. Abbaspour Tehrani, K.; De Kimpe, N. Curr. Org. Chem. 2009, 13, 854
2. Couty, F.; Evano, G. Synlett 2009, 3053
3. Singh, G. S.; Dhooghe, M.; De Kimpe, N. In Comprehensive Heterocyclic Chemistry III; Katritzky, A.; Ramsden, C.; Scriven, E.; Taylor, R., Eds.; Elsevier: Oxford, 2008; Vol. 2, p 1.
4. Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988
5. Ferraris, D.; Belyakov, S.; Li, W.; Oliver, E.; Ko, Y. S.; Calvin, D.; Lautar, S.; Thomas, B.; Rojas, C. Curr. Top. Med. Chem. 2007, 7, 597
6. Couty, F.; Evano, G. Org. Prep. Proced. Int 2006, 38, 427
7. De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Oxford, 1996; Vol. 1B, p 507.
8. Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331
9. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Rev. 2007, 107, 4437
10. Dejaegher, Y.; Kuz'menok, N. M.; Zvonok, A. M.; De Kimpe, N. Chem. Rev. 2002, 102, 29
11. Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226
12. Denis, J.-B.; Masson, G.; Retailleau, P.; Zhu, J. Angew. Chem., Int. Ed. 2011, 50, 5356
13. Shindoh, N.; Kitaura, K.; Takemoto, Y.; Takasu, K. J. Am. Chem. Soc. 2011, 133, 8470
14. Alcaide, B.; Almendros, P.; Luna, A.; Torres, M. R. Adv. Synth. Catal. 2010, 352, 621
15. Feula, A.; Male, L.; Fossey, J. S. Org. Lett. 2010, 12, 5044
16. Shindoh, N.; Takemoto, Y.; Takasu, K. Chem. Eur. J. 2009, 15, 7026
17. Ungureanu, I.; Klotz, P.; Schoenfelder, A.; Mann, A. Chem. Commun. 2001, 958
18. Li, G.-Q.; Li, Y.; Dai, L.-X.; You, S.-L. Org. Lett. 2007, 9, 3519
19. Zhao, L.; Li, C.-J. Chem. Asian J. 2006, 1-2, 203
20. Vargas-Sanchez, M.; Couty, F.; Evano, G.; Prim, D.; Marrot, J. Org. Lett. 2005, 7, 5861
21. Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Org. Lett. 2005, 7, 3981
22. Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 4572
23. Durst, T.; Elzen, R. V. D.; LeBelle, M. J. J. Am. Chem. Soc. 1972, 94, 9261
24. Clader, J. W. Curr. Top. Med. Chem. 2005, 5, 243
25. Setti, E. L.; Micetich, R. G. Curr. Med. Chem. 1998, 5, 101
26. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993.
27. Neuhaus, F. C.; Georgeopapadakou, N. H. In Emerging Targets in Antibacterial and Antifungal Chemoterapy; Sutcliffe, J.; Georgeopapadakou, N. H., Eds.; Chapman and Hall: New York, 1992.
28. Chen, C. T.; Chan, Y. S.; Tzeng, Y. R.; Chen, M. T. Dalton Trans. 2004, 2691
29. Schaffer, P.; Morel, P.; Britten, J. F.; Valliant, J. F. Inorg. Chem. 2002, 41, 6493
30. Marchand, E.; Morel, G.; Sinbandhit, S. Eur. J. Org. Chem. 1999, 1729
31. Aumann, R.; Heinen, H. Chem. Ber. 1986, 119, 2289
32. Labbé, G.; Sorgeloos, D.; Toppet, S. Tetrahedron Lett. 1982, 23, 2909
33. Deyrup, J. A.; Vestling, M. M.; Hagan, W. V.; Yun, H. Y. Tetrahedron 1969, 25, 1467
34. Xu, X.; Cheng, D.; Li, J.; Guo, H.; Yan, J. Org. Lett. 2007, 9, 1585
35. Kim, S. H.; Park, S. H; Choi, J. H.; Chang, S. Chem. Asian J. 2011, 6, 2618
36. Nishiura, M.; Hou, Z. Bull. Chem. Soc. Jpn. 2010, 83, 595
37. Suzuki, T.; Zhang, W.-X.; Nishiura, M.; Hou, Z. J. Synth. Org. Chem. Jpn. 2009, 67, 451
38. Shen, H.; Xie, Z. J. Organomet. Chem. 2009, 694, 1652
39. Zhang, W.-X.; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720
40. Edelmann, F. T. Adv. Organomet. Chem. 2008, 57, 183
41. Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589
42. Wang, Y.; Zhang, W.-X.; Wang, Z.; Xi, Z. Angew. Chem., Int. Ed. 2011, 50, 8122
43. Li, D.; Wang, Y.; Zhang, W.-X.; Zhang, S.; Guang, J.; Xi, Z. Organometallics 2011, 30, 5278
44. Li, D.; Guang, J.; Zhang, W.-X.; Wang, Y.; Xi, Z. Org. Biomol. Chem. 2010, 8, 1816
45. Wang, Z.; Wang, Y.; Zhang, W.-X.; Hou, Z.; Xi, Z. J. Am. Chem. Soc. 2009, 131, 15108
46. Zhang, W.-X.; Li, D.; Wang, Z.; Xi, Z. Organometallics 2009, 28, 882
47. Zhang, W.-X.; Nishiura, M.; Mashiko, T.; Hou, Z. Chem. Eur. J. 2008, 14, 2167
48. Yu, R. T.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 3262
49. Xu, X.; Gao, J.; Cheng, D.; Li, J.; Qiang, G.; Guo, H. Adv. Synth. Catal. 2008, 350, 61
50. Volonterio, A.; Zanda, M. J. Org. Chem. 2008, 73, 7486
51. Zhang, W.-X.; Nishiura, M.; Hou, Z. Chem. Eur. J. 2007, 13, 4037
52. Zhang, W.-X.; Nishiura, M.; Hou, Z. Chem. Commun. 2006, 3812
53. Zhang, W.-X.; Nishiura, M.; Hou, Z. Synlett 2006, 1213
54. Zhang, W.-X.; Nishiura, M.; Hou, Z. J. Am. Chem. Soc. 2005, 127, 16788
55. Ong, T.-G.; Yap, G. P. A; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 8100
56. Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068
57. Yoo, W.-J.; Li, C.-J. Top. Curr. Chem. 2010, 292, 281
58. Li, B.-J.; Yang, S.-D.; Shi, Z.-J. Synlett 2008, 949
59. Ren, H.; Li, Z.; Knochel, P. Chem. Asian J. 2007, 2, 416
60. Deng, K.; Bensari, A.; Cohen, T. J. Am. Chem. Soc. 2002, 124, 12106
61. Wittine, K.; Benci, K.; Pavelić, S. K.; Pavelić, K.; Bratulić, S.; Hock, K.; Balzarini, J.; Mintas, M. Med. Chem. Res. 2011, 20, 280
62. Noll, S.; Kralj, M.; Šuman, L.; Stephan, H.; Piantanida, I. Eur. J. Med. Chem. 2009, 44, 1172
63. Peng, X.; Hong, I. S.; Li, H.; Seidman, M. M.; Greenberg, M. M. J. Am. Chem. Soc. 2008, 130, 10299
64. Beauchamp, L. M.; Serling, B. L.; Kelsey, J. E.; Biron, K. K.; Collins, P.; Selway, J.; Lin, J.-C.; Schaeffer, H. J. J. Med. Chem. 1988, 31, 144