[3+2] Cycloadditions of α-acyl ketene dithioacetals with propargylamines: Pyrrole synthesis in water

Tetrahedron Letters

Volumn 54, Issue 11, 2013, Pages 1478-1481

  Ren, Chuan Qing ^a   Di, Chong Hui ^a   Zhao, Yu Long ^a   Zhang, Jing Ping ^a  

^a NORTHEAST NORMAL UNIVERSITY   (China)

Author keywords

Propargylamines; Pyrroles; Synthetic methods; acyl ketene dithioacetals

Indexed keywords

ACETAL DERIVATIVE; ALPHA ACYL KETENE DITHIOACETAL DERIVATIVE; AMINE; PROPARGYLAMINE DERIVATIVE; PYRROLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 84874941014     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.020     Document Type: Article

References (84)

1. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301
2. Ahluwalia, V. K.; Varma, R. S. Green Solvents for Organic Synthesis; Alpha Science, Oxford, U.K., 2009.
3. Simon, M.-O.; Li, C.-J. Chem. Soc. Rev. 2012, 41, 1415
4. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302
5. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725
6. Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68
7. Li, C.-J. Chem. Rev. 2005, 105, 3095
8. Li, C.-J.; Chan, T.-H. Comprehensive Organic Reactions in Aqueous Media; Wiley: New York, 2007
9. Lindström, U. M. Chem. Rev. 2002, 102, 2751
10. Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741.
11. Sarrafi, Y.; Sadatshahabi, M.; Alimohammadi, K.; Tajbakhsh, M. Green Chem. 2011, 13, 2851
12. Moseley, J. D.; Kappe, C. O. Green Chem. 2011, 13, 794
13. Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454
14. De, S.; Dutta, S.; Saha, B. Green Chem. 2011, 13, 2859
15. Carvalho, L. C. R.; Fernandes, E.; Marques, M. M. B. Chem.-Eur. J. 2011, 17, 12544
16. Jung, E. J.; Park, B. H.; Lee, Y. R. Green Chem. 2010, 12, 2003
17. Ma, N.; Jiang, B.; Zhang, G.; Tu, S.-J.; Wever, W.; Li, G. Green Chem. 2010, 12, 1357
18. Ding, Q.; Cao, B.; Liu, X.; Zong, Z.; Peng, Y.-Y. Green Chem. 2010, 12, 1607
19. Zhou, Y.; Zhai, Y.; Li, J.; Ye, D.; Jiang, H.; Liu, H. Green Chem. 2010, 12, 1397
20. Kumaravel, K.; Vasuki, G. Green Chem. 2009, 11, 1945.
21. Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264
22. Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582
23. Agarwal, S.; Cämmerer, S.; Filali, S.; Fröhner, W.; Knöll, J.; Krahl, M. P.; Reddy, K. R.; Knölker, H.-J. Curr. Org. Chem. 2005, 9, 1601
24. Hoffmann, H.; Lindel, T. Synthesis 2003, 1753
25. Walsh, C. T.; Garneau-Tsodikova, S.; Howard-Jones, A. R. Nat. Prod. Rep. 2006, 23, 517.
26. Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213
27. Huffman, J. W.; Padgett, L. W. Curr. Med. Chem. 2005, 12, 1395
28. Huffman, J. W. Curr. Med. Chem. 1999, 6, 705.
29. Guernion, N. J. L.; Hayes, W. Curr. Org. Chem. 2004, 8, 637
30. Novák, P.; Müller, K.; Santhanam, K. S. V.; Haas, O. Chem. Rev. 1997, 97, 207
31. Curran, D.; Grimshaw, J.; Perera, S. D. Chem. Soc. Rev. 1991, 20, 391.
32. Jolicoeur, B.; Chapman, E. E.; Thompson, A.; Lubell, W. D. Tetrahedron 2006, 62, 11531
33. Ono, N. Heterocycles 2008, 75, 243.
34. Pall, C. Ber. Dtsch. Chem. Ges. 1885, 18, 367
35. Banik, B. K.; Samajdar, S.; Banik, I. J. Org. Chem. 2004, 69, 213
36. Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 24, 5277.
37. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474
38. Palacios, F.; Aparicio, D.; De los Santos, J. M.; Vicario, J. Tetrahedron 2001, 57, 1961.
39. For reviews, see: Van Leusen, D.; Van Leusen, A. M. Org. React. 2001, 57, 417.
40. Jiang, Y.; Chan, W. C.; Park, C.-M. J. Am. Chem. Soc. 2012, 134, 4104
41. Trost, B. M.; Lumb, J.-P.; Azzarelli, J. M. J. Am. Chem. Soc. 2011, 133, 740
42. Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585
43. Mizuno, A.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2009, 48, 8318
44. Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664
45. Kim, J. T.; Keľin, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2003, 42, 98
46. Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260
47. Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468
48. Tejedor, D.; González-Cruz, D.; García-Tellado, F.; Marrero-Tellado, J. J.; Rodríguez, M. L. J. Am. Chem. Soc. 2004, 126, 8390
49. Barber, D. M.; Sanganee, H.; Dixon, D. J. Chem. Commun. 2011, 47, 4379
50. Kramer, S.; Madsen, J. L. H.; Rottländer, M.; Skrydstrup, T. Org. Lett. 2010, 12, 2758
51. Ackermann, L.; Sandmann, R.; Kaspar, T. Org. Lett. 2009, 11, 2031
52. Merkul, E.; Boersch, C.; Frank, W.; Müller, T. J. J. Org. Lett. 2009, 11, 2269
53. Wang, Y.-F.; Toh, K. K.; Chiba, S.; Narasaka, K. Org. Lett. 2008, 10, 5019.
54. Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238
55. Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2010, 39, 4402
56. Frolova, L. V.; Evdokimov, N. M.; Hayden, K.; Malik, I.; Rogelj, S.; Kornienko, A.; Magedov, I. V. Org. Lett. 2011, 13, 1118
57. Maiti, S.; Biswas, S.; Jana, U. J. Org. Chem. 2010, 75, 1674
58. St. Cyr, D. J.; Martin, N.; Arndtsen, B. A. Org. Lett. 2007, 9, 449
59. Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465
60. Cadierno, V.; Gimeno, J.; Nebra, N. Chem. Eur. J. 2007, 13, 9973.
61. Rueping, M.; Parra, A. Org. Lett. 2010, 12, 5281 (from (E)-bromonitrostyrenes and enaminones)
62. Khalili, B.; Jajarmi, P.; Eftekhari-Sis, B.; Hashemi, M. M. J. Org. Chem. 2008, 73, 2090 (three-component reaction of β-dicarbonyl compounds with arylglyoxals in the presence of ammonium acetate).
63. Han, X.-D.; Zhao, Y.-L.; Meng, J.; Ren, C.-Q.; Liu, Q. J. Org. Chem. 2012, 77, 5173
64. Zhao, Y.-L.; Yang, S.-C.; Di, C.-H.; Han, X.-D.; Liu, Q. Chem. Commun. 2010, 46, 7614
65. Zhao, Y.-L.; Chen, L.; Yang, S.-C.; Tian, C.; Liu, Q. J. Org. Chem. 2009, 74, 5622
66. Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
67. Li, Y.; Xu, X.; Tan, J.; Xia, C.; Zhang, D.; Liu, Q. J. Am. Chem. Soc. 2011, 133, 1775
68. Tan, J.; Xu, X.; Zhang, L.; Li, Y.; Liu, Q. Angew. Chem., Int. Ed. 2009, 48, 2868
69. Wang, H.; Zhao, Y.-L.; Ren, C.-Q.; Diallo, A.; Liu, Q. Chem. Commun. 2011, 47, 1236
70. Meng, J.; Zhao, Y.-L.; Ren, C.-Q.; Li, Y.; Li, Z.; Liu, Q. Chem. Eur. J. 2009, 15, 1830
71. Zhao, Y.-L.; Li, D.-Z.; Han, X.-D.; Chen, L.; Liu, Q. Adv. Synth. Catal. 2008, 350, 1537
72. Zhao, Y.-L.; Zhang, W.; Wang, S.; Liu, Q. J. Org. Chem. 2007, 72, 4985
73. Chen, L.; Zhao, Y.-L.; Liu, Q.; Chen, C.; Piao, C.-R. J. Org. Chem. 2007, 72, 9259.
74. Jon Grenning, A. J.; Tunge, A. Angew. Chem., Int. Ed. 2011, 50, 1688
75. Yuan, H.; Wang, M.; Liu, Y.; Wang, L.; Liu, J.; Liu, Q. Chem. Eur. J. 2010, 16, 13450.
76. Zhao, Y.-L.; Di, C.-H.; Liu, S.-D.; Meng, J.; Liu, Q. Adv. Synth. Catal. 2012, 354, 3545.
77. Ouyang, Y.; Dong, D.; Yu, H.; Liang, Y.; Liu, Q. Adv. Synth. Catal. 2006, 348, 206
78. Dong, D.; Ouyang, Y.; Yu, H.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
79. Dieter, R. K. Tetrahedron 1986, 42, 3029
80. Junjappa, H.; Ila, H.; Asokan, C. V. Tetrahedron 1990, 46, 5423.
81. Xin, X.; Wang, D.; Li, X.; Wan, B. Angew. Chem., Int. Ed. 2012, 51, 1693
82. Cacchi, S.; Fabrizi, G.; Filisti, E. Org. Lett. 2008, 10, 2629
83. Mo, D.-L.; Ding, C.-H.; Dai, L.-X.; Hou, X.-L. Chem. Asian J. 2011, 6, 3200
84. Misra, N. C.; Panda, K.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1246.