Synthesis of functionalized coumarins and quinolinones by NHC-catalyzed annulation of modified enals with heterocyclic C-H acids

Journal of Organic Chemistry

Volumn 79, Issue 9, 2014, Pages 4245-4251

  Yetra, Santhivardhana Reddy ^a   Roy, Tony ^a   Bhunia, Anup ^a   Porwal, Digvijay ^a   Biju, Akkattu T ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ENANTIOSELECTIVITY;

ENANTIOSELECTIVE; FUNCTIONALIZED; LACTONIZATION; N-HETEROCYCLIC CARBENES;

ORGANIC COMPOUNDS;

2 BROMOENAL; ACID; ALDEHYDE; AZOLIUM; CARBENE; CARBON; COUMARIN DERIVATIVE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; HYDROGEN; LACTAM DERIVATIVE; LACTONE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; METHANE; QUINOLONE DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; HYDROGEN BOND; LACTAMIZATION; LACTONIZATION; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY;

ACIDS; CATALYSIS; COUMARINS; HETEROCYCLIC COMPOUNDS; METHANE; MOLECULAR STRUCTURE; QUINOLONES;

EID: 84899832307     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500693h     Document Type: Article

References (73)

1. Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2005, 48, 6400
2. Xie, L.; Takeuchi, Y.; Cosentino, L. M.; McPhail, A. T.; Lee, K.-H. J. Med. Chem. 2001, 44, 664
3. Yu, D.; Suzuki, M.; Xie, L.; Morris-Natschke, S. L.; Lee, K.-H. Med. Res. Rev. 2003, 23, 322
4. Xu, D.-Q.; Wang, Y.-F.; Zhang, W.; Luo, S.-P.; Zhong, A.-G.; Xia, A.-B.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 4177
5. Rueping, M.; Merino, E.; Sugiono, E. Adv. Synth. Catal. 2008, 350, 2127
6. Appendino, G.; Cravotto, G.; Tagliapietra, S.; Nan, G. M.; Palmisano, G. Helv. Chim. Acta 1990, 73, 1865
7. Dong, J.; Du, D.-M. Org. Biomol. Chem. 2012, 10, 8125
8. Zhu, X.; Lin, A.; Shi, Y.; Guo, J.; Zhu, C.; Cheng, Y. Org. Lett. 2011, 13, 4382
9. Dong, Z.; Wang, L.; Chen, X.; Liu, X.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2009, 5192
10. Kim, H.; Yen, C.; Preston, P.; Chin, J. Org. Lett. 2006, 8, 5239
11. Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 4955
12. Boschetti, E.; Molho, D.; Fontaine, L. Derivatives of 4-hydroxy coumarin, U. S. Patent, 3,574,234; Apr 6, 1971.
13. Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1491
14. Yao, T.; Yue, D.; Larock, R. C. J. Org. Chem. 2005, 70, 9985
15. Singh, R. P.; Singh, D. Heterocycles 1985, 23, 903
16. De Sarkar, S.; Biswas, A.; Samanta, R. C.; Studer, A. Chem.-Eur. J. 2013, 19, 4664
17. Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906
18. Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 351
19. Izquierdo, J.; Hutson, G. E.; Cohen, D. T.; Scheidt, K. A. Angew. Chem., Int. Ed. 2012, 51, 11686
20. Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
21. Vora, H. U.; Wheeler, P.; Rovis, T. Adv. Synth. Catal. 2012, 354, 1617
22. Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295
23. Knappke, C. E. I.; Imami, A.; Jacobi von Wangelin, A. ChemCatChem 2012, 4, 937
24. Biju, A. T.; Kuhl, N.; Glorius, F. Acc. Chem. Res. 2011, 44, 1182
25. Nair, V.; Menon, R. S.; Biju, A. T.; Sinu, C. R.; Paul, R. R.; Jose, A.; Vellalath, S. Chem. Soc. Rev. 2011, 40, 5336
26. Chiang, P.-C.; Bode, J. W. In N-Heterocyclic Carbenes; The Royal Society of Chemistry: London, 2011; p 399.
27. Nair, V.; Vellalath, S.; Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691
28. Enders, D.; Niemeier, O.; Henseler, H. Chem. Rev. 2007, 107, 5606
29. Candish, L.; Forsyth, C. M.; Lupton, D. W. Angew. Chem., Int. Ed. 2013, 52, 9149
30. Cheng, J.; Huang, Z.; Chi, Y. R. Angew. Chem., Int. Ed. 2013, 52, 8592
31. Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2013, 135, 58
32. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2011, 133, 4694
33. Ryan, S. J.; Candish, L.; Lupton, D. W. J. Am. Chem. Soc. 2009, 131, 14176
34. Lai, C.-L.; Lee, H. M.; Hu, C.-H. Tetrahedron Lett. 2005, 46, 6265
35. Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453
36. Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587
37. Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583
38. Samanta, R. C.; De Sarkar, S.; Frøhlich, R.; Grimme, S.; Studer, A. Chem. Sci. 2013, 4, 2177
39. Samanta, R. C.; Maji, B.; De Sarkar, S.; Bergander, K.; Fröhlich, R.; Mück-Lichtenfeld, C.; Mayr, H.; Studer, A. Angew. Chem., Int., Ed. 2012, 51, 5234
40. Kravina, A. G.; Mahatthananchai, J.; Bode, J. W. Angew. Chem., Int. Ed. 2012, 51, 9433
41. Mahatthananchai, J.; Kaeobamrung, J.; Bode, J. W. ACS Catal. 2012, 2, 494
42. Lyngvi, E.; Bode, J. W.; Schoenebeck, F. Chem. Sci. 2012, 3, 2346
43. Mahatthananchai, J.; Zheng, P.; Bode, J. W. Angew. Chem., Int. Ed. 2011, 50, 1673
44. Wanner, B.; Mahatthananchai, J.; Bode, J. W. Org. Lett. 2011, 13, 5378
45. Biswas, A.; De Sarkar, S.; Fröhlich, R.; Studer, A. Org. Lett. 2011, 13, 4966
46. Rong, Z.-Q.; Jia, M.-Q.; You, S.-L. Org. Lett. 2011, 13, 4080
47. De Sarkar, S.; Studer, A. Angew. Chem., Int. Ed. 2010, 49, 9266
48. Zhu, Z.-Q.; Zheng, X.-L.; Jiang, N.-F.; Wan, X.; Xiao, J.-C. Chem. Commun. 2011, 47, 8670
49. Kaeobamrung, J.; Mahatthananchai, J.; Zheng, P.; Bode, J. W. J. Am. Chem. Soc. 2010, 132, 8810
50. Zhu, Z.-Q.; Xiao, J.-C. Adv. Synth. Catal. 2010, 352, 2455
51. Zeitler, K. Org. Lett. 2006, 8, 637
52. Yetra, S. R.; Kaicharla, T.; Kunte, S. S.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2013, 15, 5202
53. Zhang, H.-R.; Dong, Z.-W.; Yang, Y.-J.; Wang, P.-L.; Hui, X.-P. Org. Lett. 2013, 15, 4750
54. Yetra, S. R.; Bhunia, A.; Patra, A.; Mane, M. V.; Vanka, K.; Biju, A. T. Adv. Synth. Catal. 2013, 355, 1089
55. Yao, C.; Jiao, W.; Xiao, Z.; Liu, R.; Li, T.; Yu, C. Tetrahedron 2013, 69, 1133
56. Wang, X.-B.; Zou, X.-L.; Du, G.-F.; Liu, Z.-Y.; Dai, B. Tetrahedron 2012, 68, 6498
57. Zhang, B.; Feng, P.; Cui, Y.; Jiao, N. Chem. Commun. 2012, 48, 7280
58. Yao, C.; Wang, D.; Lu, J.; Li, T.; Jiao, W.; Yu, C. Chem.-Eur. J. 2012, 18, 1914
59. Sun, F.-G.; Sun, L.-H.; Ye, S. Adv. Synth. Catal. 2011, 353, 3134
60. Bhunia, A.; Patra, A.; Puranik, V.; Biju, A. T. Org. Lett. 2013, 15, 1756
61. Sinu, C. R.; Padmaja, D. V. M; Ranjini, U. P.; Seetha Lakshmi, K. C.; Suresh, E.; Nair, V. Org. Lett. 2013, 15, 68
62. Ding, D.; Wang, Z. Eur. J. Org. Chem. 2008, 4949
63. Nair, V.; Sinu, C. R.; Rejithamol, R.; Seethalakshmi, K. C.; Suresh, E. Org. Biomol. Chem. 2011, 9, 5511
64. Phillips, E. M.; Wadamoto, M.; Roth, H. S.; Andrew, W. O.; Scheidt, K. A. Org. Lett. 2009, 11, 105
65. Struble, J. R.; Bode, J. W. Org. Synth. 2010, 87, 362
66. Mahatthananchai, J.; Bode, J. W. Chem. Sci. 2012, 3, 192
67. Itoh, K.; Hasegawa, M.; Tanaka, J.; Kanemasa, S. Org. Lett. 2005, 7, 979
68. Ray, S. K.; Singh, P. K.; Molleti, N.; Singh, V. K. J. Org. Chem. 2012, 77, 8802
69. Allen, C. F. H.; Edens, C. O., Jr. Org. Synth. 1945, 25, 92
70. Li, W.; Li, J.; Wan, Z.-K.; Wu, J.; Massefski, W. Org. Lett. 2007, 9, 4607
71. Arduengo, A. J.; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523
72. Cooke, J.; Lightbody, O. C. J. Chem. Educ. 2009, 86, 610
73. Yavari, I.; Sabbaghan, M.; Hossaini, Z. Synlett 2008, 8, 1153