Regioselective Metal-Free Decarboxylative Multicomponent Coupling of α-Amino Acids, Aldehydes and Isonitriles Leading to N-Substituted Azacyclic-2-carboxamides with Antithrombotic Activity

Journal of Organic Chemistry

Volumn 80, Issue 1, 2015, Pages 99-108

  Dighe, Shashikant U ^a   Kumar, Anil K S ^a   Srivastava, Smriti ^a   Shukla, Pankaj ^a   Singh, Surendra ^a   Dikshit, Madhu ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBOXYLATION; SUBSTITUTION REACTIONS;

ALPHA-AMINO ACIDS; ANTI-THROMBOTIC ACTIVITIES; IMINE FORMATION; INHIBITION OF PLATELET AGGREGATION; MULTI-COMPONENT COUPLING; PIPECOLIC ACID; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS;

REGIOSELECTIVITY;

ALDEHYDE DERIVATIVE; ALPHA AMINO ACID; AMIDE; ANTICOAGULANT AGENT; AZACYCLIC 2 CARBOXAMIDE DERIVATIVE; ISONITRILE DERIVATIVE; PIPECOLIC ACID DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTICOAGULATION; ARTICLE; DECARBOXYLATION; DRUG SYNTHESIS; HYDROLYSIS; STEREOCHEMISTRY; THROMBOCYTE AGGREGATION INHIBITION;

EID: 84937686364     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502029k     Document Type: Article

References (78)

1. Gooßen, L. J.; Rodriguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100-3120
2. Rodriguez, N.; Gooßen, L. J. Chem. Soc. Rev. 2011, 40, 5030-5048
3. Dzik, W. I.; Lange, P. L.; Gooßen, L. J. Chem. Sci. 2012, 3, 2671-2678
4. Cornella, J.; Larrosa, I. Synthesis 2012, 44, 653-676
5. Gooßen, L. J.; Gooßen, K. Top. Organomet. Chem. 2013, 44, 121-142
6. Park, K.; Lee, S. RSC Adv. 2013, 3, 14165-14182
7. Tang, J.; Gooßen, L. J. Org. Lett. 2014, 16, 2664-2667
8. Guntreddi, T.; Vanjari, R.; Singh, K. N. Org. Lett. 2014, 16, 3624-3627
9. Suresh, R.; Muthusubramanian, S.; Kumaran, R. S.; Manickam, G. Asian J. Org. Chem. 2014, 3, 604-608
10. Cahiez, G.; Moyeux, A.; Poizat, M. Chem. Commun. 2014, 50, 8982-8984
11. Min, H.; Palani, T.; Park, K.; Hwang, J.; Lee, S. J. Org. Chem. 2014, 79, 6279-6285
12. Mino, T.; Yoshizawa, E.; Watanabe, K.; Abe, T.; Hirai, K.; Sakamoto, M. Tetrahedron Lett. 2014, 55, 3184-3188
13. Fromm, A.; van Wuellen, C.; Hackenberger, D.; Goossen, L. J. J. Am. Chem. Soc. 2014, 136, 10007-10023
14. Xiong, H.-Y.; Yang, Z.-Y.; Chen, Z.; Zeng, J.-L.; Nie, J.; Ma, J.-A. Chem.-Eur. J. 2014, 20, 8325-8329
15. Rouchet, J.-B.; Schneider, C.; Spitz, C.; Lefevre, J.; Dupas, G.; Fruit, C.; Hoarau, C. Chem.-Eur. J. 2014, 20, 3610-3615
16. Chen, F.; Wong, N W. Y.; Forgione, P. Adv. Synth. Catal. 2014, 356, 1725-1730
17. Rizzi, G. P. J. Org. Chem. 1970, 35, 2069-2072
18. Grigg, R.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 180-181
19. Grigg, R.; Aly, M. F.; Sridharan, V.; Thianpatanagul, S. J. Chem. Soc., Chem. Commun. 1984, 182-183
20. Padwa, A. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984; Vol. 2.
21. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863-910
22. Padwa, A.; Pearson, W. H. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Wiley: Chichester, U.K., 2002; Vol. 59.
23. Najera, C.; Sansano, J. M. Curr. Org. Chem. 2003, 7, 1105-1150
24. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765-2810
25. Pandey, G.; Banerjee, P.; Gadre, S. R. Chem. Rev. 2006, 106, 4484-4517
26. Bonin, M.; Chauveau, A.; Micouin, L. Synlett 2006, 2349-2363
27. Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247-12275
28. Najera, C.; Sansano, J. M. Top. Heterocycl. Chem. 2008, 12, 117-145
29. Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887-2902
30. Nyerges, M.; Toth, J.; Groundwater, P. W. Synlett 2008, 1269-1278
31. Pineiro, M.; Pinho e Melo, T. M. V. D. Eur. J. Org. Chem. 2009, 5287-5307
32. Burrell, A. J. M.; Coldham, I. Curr. Org. Synth. 2010, 7, 312-331
33. Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784-6794
34. Muncipinto, G. Cycloaddition Reactions in Diversity-Oriented Synthesis: Basics and Applications. In Organic Synthesis, Drug Discovery, and Chemical Biology; Trabocchi, A., Ed.; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2013.
35. Narayan, R.; Potowski, M.; Jia, Z.-J.; Antonchick, A. P.; Waldmann, H. Acc. Chem. Res. 2014, 47, 1296-1310
36. Bi, H.-P.; Zhao, L.; Liang, Y.-M.; Li, C.-J. Angew. Chem, Int. Ed. 2009, 48, 792-795
37. Das, D.; Richers, M. T.; Ma, L.; Seidel, D. Org. Lett. 2011, 13, 6584-6587
38. Zhang, C.; Seidel, D. J. Am. Chem. Soc. 2010, 132, 1798-1799
39. Yang, D.; Zhao, D.; Mao, L.; Wang, L.; Wang, R. J. Org. Chem. 2011, 76, 6426-6431
40. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Princep, M. R. Nat. Prod. Rep. 2013, 30, 237-323
41. Hou, Y.; Tianero, M. D. B.; Kwan, J. C.; Wyche, T. P.; Michel, C. R.; Ellis, G. A.; Rivera, E. V.; Braun, D. R.; Rose, W. E.; Schmidt, E. W.; Bugni, T. S. Org. Lett. 2012, 14, 5050-5053
42. Pettit, G. R.; Smith, T. H.; Xu, J.-P.; Herald, D. L.; Flahive, E. J.; Anderson, C. R.; Belcher, P. E.; Knight, J. C. J. Nat. Prod. 2011, 74, 1003-1008
43. Adams, B.; Pörzgen, P.; Pittman, E.; Yoshida, W. Y.; Westenburg, H. E.; Horgen, F. D. J. Nat. Prod. 2008, 71, 750-754
44. St. Laurent, D. R.; Serrano-Wu, M. H.; Belema, M.; Ding, M.; Fang, H.; Gao, M.; Goodrich, J. T.; Krause, R. G.; Lemm, J. A.; Liu, M.; Lopez, O. D.; Nguyen, V. N.; Nower, P. T.; O'Boyle, D. R., II; Pearce, B. C.; Romine, J. L.; Valera, L.; Sun, J.-H.; Wang, Y.-K.; Yang, F.; Yang, X.; Meanwell, N. A.; Snyder, L. B. J. Med. Chem. 2014, 57, 1976-1994
45. Furet, P.; Guagnano, V.; Fairhurst, R. A.; Imbach-Weese, P.; Bruce, I.; Knapp, M.; Fritsch, C.; Blasco, F.; Blanz, J.; Aichholz, R.; Hamon, J.; Fabbro, D.; Caravatt, G. Bioorg. Med. Chem. 2013, 23, 3741-3748
46. Moore, B. P.; Chung, D. H.; Matharu, D. S.; Golden, J. E.; Maddox, C.; Rasmussen, L.; Noah, J. W.; Sosa, M. I.; Ananthan, S.; Tower, N. A.; White, E. L.; Jia, F.; Prisinzano, T. E.; Aubé, J.; Jonsson, C. B.; Severson, W. E. J. Med. Chem. 2012, 55, 8582-8587
47. Rabey, F. M.; Gadepalli, R. S. V. S.; Diano, S.; Cheng, Q.; Tabrizian, T.; Gailani, D.; Rimoldi, J. M.; Madar, Z. S. Curr. Med. Chem. 2012, 19, 4194-4206
48. Chobanian, H.; Biftu, T.; Pio, B.; Wu, Z. WO 2014081618 A1, 2014
49. Chem. Abstr. 161, 39572.
50. Caravatti, G.; Fairhurst, R. A.; Furet, P.; Guagnano, V.; Imbach, P. US 20090163469 A1, 2009
51. Chem. Abstr. 151, 101486.
52. Kumar, A. K. S.; Misra, A.; Siddiqi, T. I.; Srivastava, S.; Jain, M.; Bhatta, R. S.; Barthwal, M.; Dikshit, M.; Dikshit, D. K. Eur. J. Med. Chem. 2014, 81, 456-472
53. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinheim, Germany, 2005.
54. Tang, Z.; Jiang, F.; Cui, X.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5755-5760
55. Chen, J.-R.; Lu, H.-H.; Li, X.-Y.; Cheng, L.; Wan, J.; Xiao, W.-J. Org. Lett. 2005, 7, 4543-4545
56. Dalko, P. I., Ed. Enantioselective Organocatalysis; Wiley-VCH: Weinheim, Germany, 2007.
57. Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138-6171
58. Bisai, V.; Bisai, A.; Singh, V. K. Tetrahedron 2012, 68, 4541-4580
59. Liu, L.; Gao, M.-N.; Li, Y.; Li, Z.; Song, L.; Liu, Z.-W.; Xue, D.; Liu, Z.-T. Curr. Org. Chem. 2013, 17, 1563-1568
60. Delaney, J. P.; Brozinskia, H. L.; Henderson, L. C. Org. Biomol. Chem. 2013, 11, 2951-2960
61. Guan, Z.; Luo, Y.; Zhang, B.-Q.; Heinen, K.; Yang, D.-C.; He, Y.-H. Tetrahedron: Asymmetry 2014, 25, 802-812
62. Moles, F. J. N.; Guillena, G.; Najera, C. RSC Adv. 2014, 4, 9963-9966
63. Wang, Y.; Ji, S.; Wei, K.; Lin, J. RSC Adv. 2014, 4, 30850-30856
64. Pattabiraman, V.; Bode, J. W. Nature 2011, 480, 471-479
65. Lang, S. Chem. Soc. Rev. 2013, 42, 4867-4880
66. Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257-5269
67. Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084-7097
68. Chakrabarty, S.; Choudhary, S.; Doshi, A.; Liu, F.-Q.; Mohan, R.; Ravindra, M. P.; Shah, D.; Yang, X.; Fleming, F. F. Adv. Synth. Catal. 2014, 356, 2135-2196
69. Bhowmik, S.; Pandey, G.; Batra, S. Chem.-Eur. J. 2013, 19, 10487-10491
70. Pandey, G.; Bhowmik, S.; Batra, S. Org. Lett. 2013, 15, 5044-5047
71. Yadav, V. D.; Dighe, S. U.; Batra, S. RSC Adv. 2014, 4, 57587-57590
72. Pandey, G.; Bhowmik, S.; Batra, S. RSC Adv. 2014, 4, 41433-41436
73. Ugi, I.; Demharter, A.; Hõri, W.; Schmid, T. Tetrahedron 1996, 52, 11657-11664
74. Cheng, H.; Smith, C. R.; Wang, Y.; Parrott, T. J.; Dress, K. R.; Nair, S. K.; Hoffman, J. E.; Le, P. T. Q.; Kupchinsky, S. W.; Yang, Y.; Cripps, S. J.; Huang, B. WO 2005108359 A1, 2005
75. Chem. Abstr. 143, 478200.
76. O'Neil, I. A.; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515-518
77. Traverse, J. F.; Zhao, Y.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2005, 7, 3151-3154
78. Ghorai, M. K.; Samanta, S.; Das, S. Chem.-Asian J. 2013, 2, 1026-1030