L-Proline-catalyzed five-component domino reaction leading to multifunctionalized 1,2,3,4-tetrahydropyridines

Tetrahedron

Volumn 66, Issue 51, 2010, Pages 9721-9728

  Jiang, Huan Feng ^a   Li, Jing Hao ^a   Chen, Zheng Wang ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

CDYYBNWISYDSCG UHFFFAOYSA N; IEYWRSPZBKQLDO UHFFFAOYSA N; JDOQXOBOBFEANS UHFFFAOYSA N; KGYNHXHXWXBZIH UHFFFAOYSA N; LEDKZVJEJPMKMW UHFFFAOYSA N; NPMILCMNOGSRGL UHFFFAOYSA N; NUZAORWTTWTPRI UHFFFAOYSA N; QAXUNCMIEUQXLX UHFFFAOYSA N

Indexed keywords

1 ETHYL 5 (4 METHYLBENZOYL) 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 1 METHYL 5 (4 METHYLBENZOYL) 6 4 TOLYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 1 METHYL 5 (4 METHYLBENZOYL) 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H)DICARBONITRILE; 1,1' [1 ETHYL 5 (4 METHYLBENZOYL) 6 PHENYL 1,2,3,4 TETRAHYDROPYRIDINE 3,3 DIYL]DIETHANONE; 1,1' [1 METHYL 5 (4 METHYLBENZOYL) 6 PHENYL 1,2,3,4 TETRAHYTETRAHYDROPYRIDINE 3,3 DIYL]DIETHANONE; 1,10 (5 BENZOYL 1 METHYL 6 4 TOLYL 1,2,3,4 TETRAHYDROPYRIDINE 3,3 DIYL)DIETHANONE; 1,10 (5 BENZOYL 1 METHYL 6 PHENYL 1,2,3,4 TETRAHYDROPYRIDINE 3,3 DIYL)DIETHANONE; 2 PIPERIDEINE DERIVATIVE; 5 (4 FLUOROBENZOYL) 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 5 (CYCLOHEXANECARBONYL) 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 5 (FURAN 2 CARBONYL) 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 5 BENZOYL 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBONITRILE; 5 BENZOYL 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBOXYLATE; DIETHYL 5 (FURAN 2 CARBONYL) 1 METHYL 6 PHENYL 1,2 DIHYDROPYRIDINE 3,3(4H) DICARBOXYLATE; ETHYL 1 (4 BROMOPHENYL) 5,5 DICYANO 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 1 BENZYL 5,5 DICYANO 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 3 ACETYL 1 METHYL 5 (4 METHYLBENZOYL) 6 PHENYL 1,2,3,4 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 3 ACETYL 5 BENZOYL 1 METHYL 6 PHENYL 1,2,3,4 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 3,5 DIBENZOYL 1 METHYL 6 PHENYL 1,2,3,4 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 5,5 DICYANO 1 (4 METHOXYPHENYL) 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 5,5 DICYANO 1 ETHYL 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 5,5 DICYANO 2 METHYL 1 4 TOLYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; ETHYL 5,5 DICYANO 2 METHYL 1,4,5,6 TETRAHYDROPYRIDINE 3 CARBOXYLATE; PROLINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MANNICH REACTION; ONE POT SYNTHESIS; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 78650193724     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.041     Document Type: Article

References (76)

1. For recent reviews of multicomponent reactions, see:
2. A. Dömling Chem. Rev. 106 2006 17
3. D.J. Ramón, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
4. B.B. Touré, and D.G. Hall Chem. Rev. 109 2009 4439
5. L.F. Tietze Chem. Rev. 96 1996 115
6. For recent examples on multicomponent reactions, see:
7. J. Brioche, G. Masson, and J. Zhu Org. Lett. 12 2010 1432
8. S. Maiti, S. Biswas, and U. Jana J. Org. Chem. 75 2010 1674
9. R. Scheffelaar, M. Paravidino, D. Muilwijk, M. Lutz, A.L. Spek, F.J.J. de Kanter, R.V.A. Orru, and E. Ruijter Org. Lett. 11 2009 125
10. E.J. Yoo, S.H. Park, S.H. Lee, and S. Chang Org. Lett. 11 2009 1155
11. G. Dou, C. Shi, and D. Shi J. Comb. Chem. 10 2008 810
12. D. Bonne, M. Dekhane, and J. Zhu Angew. Chem., Int. Ed. 46 2007 2485
13. D.-M. Li, L.-P. Song, X.-F. Li, C.-H. Xing, W.-M. Peng, and S.-Z. Zhu Eur. J. Org. Chem. 2007 3520
14. A.R. Siamaki, and B.A. Arndtsen J. Am. Chem. Soc. 128 2006 6050
15. X.-H. Duan, X.-Y. Liu, L.-N. Guo, M.-C. Liao, W.-M. Liu, and Y.-M. Liang J. Org. Chem. 70 2005 6980
16. G. Aridoss, S. Amirthaganesan, and Y.T. Jeong Bioorg. Med. Chem. Lett. 20 2010 2242
17. M. Malviya, Y.C. Sunil Kumar, R.B. Mythri, C. Venkateshappa, M.N. Subhash, and K.S. Rangappa Bioorg. Med. Chem. Lett. 17 2009 5526
18. J. Ishida, K. Hattori, H. Yamamoto, A. Iwashita, K. Mihara, and N. Matsuoka Bioorg. Med. Chem. Lett. 15 2005 4221
19. N.K. Suleman, J. Flores, J.M. Tanko, E.M. Isin, and N. Castagnoli Jr. Bioorg. Med. Chem. 16 2008 8557
20. D.S. Wimalasena, R.P. Perera, B.J. Heyen, I.S. Balasooriya, and K. Wimalasena J. Med. Chem. 51 2008 760
21. P.G. Dunbar, G.J. Durant, T. Rho, B. Ojo, and W.S. Messer Jr. J. Med. Chem. 37 1994 2774
22. Y.X. Chao, B.P. He, and S.S.W. Tay J. Neuroimmunol. 216 2009 39
23. E. Roberts, J.P. Sanon, J.B. Sweeney, and J.A. Workman Org. Lett. 5 2003 4775
24. L.A. Rodinovskaya, A.M. Shestopalov, and K.S. Chunikihn Tetrahedron 58 2002 4273
25. For some examples on the synthesis of multiplysubstituted tetrahydropyridines, see:
26. H. Tsukamoto, and Y. Kondo Angew. Chem., Int. Ed. 47 2008 4851
27. D.A. Spiegel, F.C. Schroeder, J.R. Duvall, and S.L. Schreiber J. Am. Chem. Soc. 128 2006 14766
28. P.V. Ramachandran, T.E. Burghardt, and L. Bland-Berry J. Org. Chem. 70 2005 7911
29. X.-F. Zhu, J. Lan, and O. Kwon J. Am. Chem. Soc. 125 2003 4716
30. C. Legault, and A.B. Charette J. Am. Chem. Soc. 125 2003 6360
31. P. Buonora, J.-C. Olsen, and T. Oh Tetrahedron 57 2001 6099
32. Y. Kita, H. Maekawa, Y. Yamasak, and I. Nishiguchi Tetrahedron 57 2001 2095
33. F.P.J.T. Rutjes, K.C.M.F. Tjen, L.B. Wolf, W.F.J. Karstens, H.E. Schoemaker, and H. Hiemstra Org. Lett. 1 1999 717
34. A.D. Abell, J. Gardiner, A.J. Phillips, and W.T. Robinson Tetrahedron Lett. 39 1998 9563
35. M.F. Braña, M. Morán, M.J. Pérez de Vega, and I. Pita-Romero J. Org. Chem. 61 1996 1369
36. M.H. Norman, and C.H. Heathcock J. Org. Chem. 53 1988 3370
37. For some examples on the synthesis of multiplysubstituted 1,2,3,4-tetrahydropyridines, see:
38. J.F. Caplan, A. Sutherland, and J.C. Vederas J. Chem. Soc., Perkin Trans. 1 2001 2217
39. T.J. Harrison, and G.R. Dake J. Org. Chem. 70 2005 10872
40. X. Li, L. Song, C. Xing, J. Zhao, and S. Zhu Tetrahedron 62 2006 2255
41. R.-G. Han, Y. Wang, Y.Y. Li, and P.F. Xu Adv. Synth. Catal. 350 2008 1474
42. N. Zanatta, L.S. da Fernandes, F.M. Nachtigall, and H.S. Ceolho Eur. J. Org. Chem. 2009 1435
43. V. Sridharan, S. Maiti, and J.C. Menéndez Chem. - Eur. J. 15 2009 4565
44. W.-B. Liu, H.-F. Jiang, S.-F. Zhu, and W. Wang Tetrahedron 65 2009 7985
45. C.A. Sperger, P. Mayer, and K.T. Wanner Tetrahedron 65 2009 10463
46. M. Zhang, H. Jiang, H. Liu, and Q. Zhu Org. Lett. 9 2007 4111
47. H. Cao, X. Wang, H. Jiang, Q. Zhu, M. Zhang, and H. Liu Chem. - Eur. J. 14 2008 11623
48. Q. Zhu, H. Jiang, J. Li, M. Zhang, X. Wang, and C. Qi Tetrahedron 65 2009 4604
49. H. Cao, H.-F. Jiang, C.-R. Qi, W.-J. Yao, and H.-J. Chen Tetrahedron Lett. 50 2009 1209
50. M. Zhang, H.F. Jiang, and A.Z. Wang Synlett 20 2007 3214
51. H. Jiang, R. Mai, H. Cao, Q. Zhu, and X. Liu Org. Biomol. Chem. 7 2009 4943
52. T.E. Müller, K.C. Hultzsch, M. Yus, F. Foubelo, and M. Tada Chem. Rev. 108 2008 3795
53. I. Tömösközi, L. Gruber, G. Kovács, I. Székely, and V. Simonidesz Tetrahedron Lett. 17 1976 4639
54. B.B. Snider, D.J. Rodini, T.C. Kirk, and R. Cordova J. Am. Chem. Soc. 104 1982 555
55. X. Tian, J.J. Jaber, and S.D. Rychnovsky J. Org. Chem. 71 2006 3176
56. For representative recent examples of proline-catalyzed reactions, see:
57. B. List, R.A. Lerner, and C.F. Barbas III J. Am. Chem. Soc. 122 2000 2395
58. K. Sakthivel, W. Notz, T. Bui, and C.F. Barbas III J. Am. Chem. Soc. 123 2001 5260
59. Y. Zhou, and Z. Shan J. Org. Chem. 71 2006 9510
60. H.J. Davies, A.M. Ruda, and N.C.O. Tomkinson Tetrahedron Lett. 48 2007 1461
61. S. Chandrasekhar, K. Vijeender, and C. Sridhar Tetrahedron Lett. 48 2007 4935
62. S. Sengupta, H. Duan, W. Lu, J.L. Petersen, and X. Shi Org. Lett. 10 2008 1493
63. B.T. Hahn, R. Fröhlich, K. Harms, and F. Glorius Angew. Chem., Int. Ed. 47 2008 9985
64. C. Zhong, Y. Chen, J.L. Petersen, N.G. Akhmedov, and X. Shi Angew. Chem., Int. Ed. 48 2009 1279
65. C. Chandler, P. Galzerano, A. Michrowska, and B. List Angew. Chem., Int. Ed. 48 2009 1978
66. C. Mukhopadhyay, P.K. Tapaswi, and R.J. Butcher Tetrahedron Lett. 51 2010 1797
67. C. Lu, and X. Lu Tetrahedron 60 2004 6575
68. Z. Li, and C.-J. Li Eur. J. Org. Chem. 2005 3173
69. B.C. Ranu, and S. Banerjee Org. Lett. 7 2005 3049
70. J. Zhang, K.D. Sarma, T.T. Curran, D.T. Belmont, and J.G. Davidson J. Org. Chem. 70 2005 5890
71. Y. Zhang, and C.-J. Li Angew. Chem., Int. Ed. 45 2006 1949
72. A. Basheer, and Z. Rappoport J. Org. Chem. 71 2006 9743
73. B.C. Ranu, K. Chattopadhyay, and L. Adak Org. Lett. 9 2007 4595
74. L. Fotouhi, M.M. Heravi, A. Fatehi, and K. Bakhtiari Tetrahedron Lett. 48 2007 5379
75. M. Saeedi, M.M. Heravi, Y.S. Beheshtiha, and H.A. Oskooie Tetrahedron 66 2010 5345
76. 3-catalyzed formation of β-enamino carbonyl compounds has been reported already, see: H. Hebbache, Z. Hank, S. Boutamine, M. Meklati, C. Bruneau, and J.-L. Renaud C.R. Chim. 11 2008 612