Regioselective synthesis of tetrahydrothiochromen-5-ones via a one-pot three-component solvent-free domino protocol

Organic Letters

Volumn 13, Issue 14, 2011, Pages 3762-3765

  Chowdhury, Sushobhan ^a   Nandi, Ganesh Chandra ^a   Samai, Subhasis ^a   Singh, Maya Shankar ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79960190015     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201458q     Document Type: Article

References (60)

1. Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301
2. Anastas, P. T.; Warner, J. C. In Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998, p. 30.
3. Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 72, 5056
4. Leitner, W. Green Chem. 2009, 11, 603
5. Zhu, J.; Bienayme, H. Multicomponent Reactions; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2005.
6. Toure, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439
7. Sunderhaus, J. D.; Martin, S. F. Chem.-Eur. J. 2009, 15, 1300
8. Ganem, B. Acc. Chem. Res. 2009, 42, 463
9. Padwa, A. Chem. Soc. Rev. 2009, 38, 3072
10. Domling, A. Chem. Rev. 2006, 106, 17
11. Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546
12. Shore, G.; Yoo, W. J.; Li, C. J.; Organ, M. Chem.-Eur. J. 2010, 16, 126
13. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602
14. Balamurugan, K.; Perumal, S.; Menendez, J. C. Tetrahedron 2011, 67, 3201
15. Muschelknautz, C.; Frank, W.; Müller, T. J. J. Org. Lett. 2011, 13, 2556
16. D'Souza, D. M.; Kiel, A.; Herten, D. P.; Müller, T. J. J. Chem.-Eur. J. 2008, 14, 529
17. D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153
18. Tanaka, K.; Toda, F. Solvent-free Organic Synthesis; Wiley-VCH: Weinheim, 2003.
19. Hernández, J. G.; Juaristi, E. J. Org. Chem. 2010, 75, 7107
20. Li, S.; Wang, J. -X.; Wen, X.; Ma, X. Tetrahedron 2011, 67, 849
21. Nelson, W. M. Green Solvents for Chemistry-Perspectives and Practice; Oxford University Press: Oxford, NY, 2003.
22. Sheldon, R. A. Green Chem. 2005, 7, 267
23. Corma, A.; Garcia, H. Chem. Rev. 2003, 103, 4307
24. Hisio, M.; Ito, T.; Eliada, Y.; Nagaoka, K.; Nomiya, Y. Japanese Patent No. 24984, 1970; Zh. Khim. 23N432P, 1966.
25. Kulikova, L. K.; Klimenko, S. K.; Stolbova, T. V.; Kharchenko, V. G. Khim.-Farm. Zh. 1976, 73
26. Wang, G.; Yang, G.; Ma, Z.; Tian, W.; Fang, B.; Linbo Li, L. Int. J. Chem. 2010, 2, 19
27. Tilak, B. D.; Vaidya, V. M. Tetrahedron Lett. 1963, 9, 487
28. Tilak, B. D.; Jain, S. K. Indian J. Chem. 1969, 7, 17
29. Kaye, P. T.; Musa, M. A.; Nchinda, A. T.; Nocanda, X. W. Synth. Commun. 2004, 34, 2575
30. Kaye, P. T. S. Afr. J. Chem. 2004, 57, 545
31. Kaltenbach, R. F.; Robinson, S. P.; Trainor, G. L. U.S. Patent 2005/0267183 A1, December 1, 2005.
32. Zhang, X.; Sui, Z. U.S. Patent 2006/0020018 A1, January 26, 2006.
33. Attila Sipos, A.; Toth, M.; Mueller, F. K. U.; Lehmann, J.; Berenyi, S. Monatsh. Chem. 2009, 140, 473
34. Katoaka, T.; Tomoto, A.; Shimizu, H.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1983, 2913
35. Banzatti, C.; Mellini, P.; Salvadori, P. Gazz. Chim. Ital. 1987, 117, 259
36. Kaye, P. T. S. Afr. J. Sci. 2004, 100, 545
37. Rasolofonjatovo, E.; Tréguier, B.; Provot, O.; Hamze, A.; Morvan, E.; Brion, J. -D.; Alami, M. Tetrahedron Lett. 2011, 52, 1036
38. Kenny, R. S.; Mashelkar, U. C.; Rane, D. M.; Bezawada, D. K. Tetrahedron 2006, 62, 9280
39. Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354
40. Usachev, B. I.; Shafeev, M. A.; Sosnovskikh, V. Y. Russ. Chem. Bull. Int. Ed. 2006, 55, 504
41. Usachev, B. I.; Sosnovskikh, V. Y.; Shafeev, M, A.; Röschenthaler, G. -V. Phosphorus, Sulfur, Silicon 2005, 180, 1315
42. Rios, R.; Sunden, H.; Ibrahem, I.; Zhao, G. -L.; Eriksson, L.; Cordova, A. Tetrahedron Lett. 2006, 47, 8547
43. Massah, A. R.; Dabagh, M.; Shahidi, S.; Naghash, H. J.; Momeni, A. R.; Aliyan, H. J. Iran. Chem. Soc. 2009, 6, 405
44. Hajipour, A. R.; Zarei, A.; Ruoho, A. E. Tetrahedron Lett. 2007, 48, 2881
45. Eshghi, H.; Rahimizadeh, M.; Saberi, S. Chin. Chem. Lett. 2008, 19, 1063
46. Zarei, A.; Hajipour, A. R.; Khazdooz, L.; Mirjalili, B. F.; Zahmatkesh, S. J. Mol. Catal. A: Chem. 2009, 301, 39
47. Nandi, G. C.; Samai, S.; Kumar, R.; Singh, M. S. Tetrahedron 2009, 65, 7129
48. Nandi, G. C.; Samai, S.; Kumar, R.; Singh, M. S. Tetrahedron Lett. 2009, 50, 7220
49. Kumar, R.; Raghuvanshi, K.; Verma, R. K.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5933
50. Verma, G. K.; Raghuvanshi, K.; Verma, R. K.; Dwivedi, P.; Singh, M. S. Tetrahedron 2011, 67, 3698
51. Samai, S.; Nandi, G. C.; Kumar, R.; Singh, M. S. Tetrahedron Lett. 2009, 50, 7096
52. Samai, S.; Nandi, G. C.; Singh, P.; Singh, M. S. Tetrahedron 2009, 65, 10155
53. Nandi, G. C.; Samai, S.; Singh, M. S. Synlett 2010, 1133
54. Samai, S.; Nandi, G. C.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5555
55. Nandi, G. C.; Samai, S.; Singh, M. S. J. Org. Chem. 2010, 75, 7785
56. Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030
57. Roy, A.; Nandi, S.; Ila, H.; Junjappa, H. Org. Lett. 2001, 3, 229
58. Verma, R. K.; Verma, G. K.; Raghuvanshi, K.; Singh, M. S. Tetrahedron 2011, 67, 584
59. Samuel, R.; Asokan, C. V.; Suma, S.; Chandran, P.; Retnamma, S.; Anabha, E. R. Tetrahedron Lett. 2007, 48, 8376
60. Crystallographic data for compound 4b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 819852. These data can be obtained free of charge at www.ccdc.cam.ac.uk.