Multifold bond cleavage and formation between meoh and quinoxalines (or benzothiazoles): Synthesis of carbaldehyde dimethyl acetals

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 966-980

  Liu, Yunkui ^a,b   Jiang, Bo ^a   Zhang, Wei ^a   Xu, Zhenyuan ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^b WENZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; BENZOTHIAZOLES; BOND CLEAVAGES; C-H BOND; CARBALDEHYDES; CROSS-COUPLINGS; DIMETHYL ACETAL; MECHANISTIC STUDIES; N-HETEROCYCLES; N-HETEROCYCLIC; QUINOXALINES; RADICAL PROCESS;

ALDEHYDES; CHEMICAL REACTIONS; TRANSITION METALS;

METHANOL;

2 BENZOTHIAZOLYL CARBALDEHYDE DIMETHYL ACETAL DERIVATIVE; 2 QUINOXALINE CARBALDEHYDE DIMETHYL ACETAL DERIVATIVE; BENZOTHIAZOLE; CARBON; HYDROGEN; METHANOL; OXYGEN; QUINOXALINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CROSS COUPLING REACTION; ONE POT SYNTHESIS;

EID: 84873338304     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302450f     Document Type: Article

References (82)

1. Olah, G. A.; Geoppert, A.; Prakash, G. K. S. Beyond Oil and Gas: The Methanol Economy; Wiley-VCH: Weinheim, Germany, 2006.
2. Tijm, P. J. A.; Waller, F. J.; Brown, D. M. Appl. Catal., A 2001, 221, 275-282
3. Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044-4098
4. Hamelinck, C. N.; Faaiji, A. P. C. J. Power Sources 2002, 111, 1-22
5. Federsel, C.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 6254-6257
6. Olah, G. A.; Geoppert, A.; Prakash, G. K. S. J. Org. Chem. 2009, 74, 487-498
7. Haynes, A. Adv. Catal. 2010, 53, 1-45
8. Kung, H. H.; Smith, K. J. Chem. Industr. 1994, 57, 175-213
9. Takaya, H.; Sugi, Y. Petrotechnology 1986, 9, 39-44
10. Jo, E.-A.; Lee, J.-H.; Jun, C.-H. Chem. Commun. 2008, 5779-5781
11. Tian, J.-S.; Miao, C.-X.; Wang, J.-Q.; Cai, F.; Du, Y.; Zhao, Y.; He, L.-N. Green Chem. 2007, 9, 566-571
12. Liu, C.; Wang, J.; Meng, L.; Deng, Y.; Li, Y.; Lei, A. Angew. Chem., Int. Ed. 2011, 50, 5144-5148
13. Xu, B.; Madix, R. J.; Friend, C. M. J. Am. Chem. Soc. 2011, 133, 20378-20383
14. Zhang, S.-Y.; He, G.; Zhao, Y.; Wright, K.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2012, 134, 7313-7316
15. Torrente, S.; Alonso, R. Org. Lett. 2001, 3, 1985-1987
16. Fernádez, M.; Alonso, R. Org. Lett. 2003, 5, 2461-2464
17. Rao, A. V. R.; Gurjar, M. K.; Devi, T. R.; Kumar, K. R. Tetrahedron Lett. 1993, 34, 1653-1658
18. Minisci, F.; Porta, O.; Recupero, F.; Punta, C.; Gambarotti, C.; Pruna, B.; Pierini, M.; Fontana, F. Synlett 2004, 874-876
19. Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937-1949 and references cited therein
20. Cui, Z.; Shang, X.; Shao, X.-F.; Liu, Z.-Q. Chem. Sci. 2012, 3, 2853-2858
21. Zbieg, J. R.; Yamaguchi, E.; Mclnturff, E. L.; Krische, M. J. Science 2012, 336, 324-327
22. Correia, C. A.; Yang, L.; Li, C.-J. Org. Lett. 2011, 13, 4581-4583
23. Zhang, S.-Y.; Tu, Y.-Q.; Fan, C.-A.; Zhang, F.-M.; Shi, L. Angew. Chem., Int. Ed. 2009, 48, 8761-8765
24. Zhang, S.-Y.; Tu, Y.-Q.; Fan, C.-A.; Jiang, Y.-J.; Shi, L.; Cao, K.; Zhang, E. Chem.-Eur. J. 2008, 14, 10201-10205
25. Jiang, Y.-J.; Tu, Y.-Q.; Zhang, E.; Zhang, S.-Y.; Cao, K.; Shi, L. Adv. Synth. Catal. 2008, 350, 552-556
26. Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A.; Zhao, Y.-M.; Xia, W.-J. J. Am. Chem. Soc. 2005, 127, 10836-10837
27. Oka, R.; Nakayama, M.; Sakaguchi, S.; Ishii, Y. Chem. Lett. 2006, 35, 1104-1105
28. Liu, Z.-Q.; Sun, L.; Wang, J.-G.; Han, J.; Zhao, Y.-K.; Zhou, B. Org. Lett. 2009, 11, 1437-1439
29. Review of C-H Activation. In Topics in Current Chemistry; Yu, J.-Q.; Shi, Z., Eds.; Springer-Verlag: Berlin, Heidelberg, 2010; Vol 292.
30. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
31. Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Res. 2012, 45, 911-922
32. Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814-825
33. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
34. Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362-3374
35. Wencel-Delord, J.; Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761
36. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780-1824
37. Godula, K.; Sames, D. Science 2006, 312, 67-72
38. Hanson, J. R. Protecting Groups in Organic Synthesis, 1 st ed.; Blackwell Science, Inc: Malden, MA, 1999.
39. Greene, T. W.; Wuts, G. M. Protecting Groups in Organic Synthesis, 3 rd ed.; John Wiley & Sons: New York, 1999.
40. Kocienski, P. J. Protecting Groups, 1 st ed.; Georg Thime Verlag: Stuttgart, 1994.
41. Gopinath, R.; Haque, S. J.; Patel, B. K. J. Org. Chem. 2002, 67, 5842-5845
42. Velusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2004, 45, 4917-4920
43. Kim, Y. J.; Varma, R. S. Tetrahedron Lett. 2005, 46, 7447-7449
44. Sminth, R. C.; Mohan, R. S. J. Org. Chem. 2002, 67, 5202-5207
45. Williams, D. B. G.; Lawton, M. C. Green Chem. 2008, 10, 914-917
46. Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. Adv. Synth. Catal. 2010, 352, 3022-3030
47. Procuranti, B.; Connon, S. J. Org. Lett. 2008, 10, 4935-4938
48. Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 8319
49. Hoskawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49-54 and references cited therein
50. Hosokawa, T.; Ohta, T.; Murahashi, S.-I. J. Chem. Soc., Chem. Commun. 1983, 848-849
51. Hosokawa, T.; Ohta, T.; Kanayama, S.; Murahashi, S.-I. J. Org. Chem. 1987, 52, 1758-1764
52. Balija, A. M.; Stowers, K. J.; Schultz, M. J.; Sigman, M. S. Org. Lett. 2006, 8, 1121-1124
53. Ochiai, M.; Miyamoto, K.; Shiro, M.; Ozawa, T.; Yamaguchi, K. J. Am. Chem. Soc. 2003, 125, 13006-13007
54. Chowdhury, A. D.; Lahiri, G. K. Chem. Commun. 2012, 48, 3448-3450
55. Li, L.-T.; Huang, J.; Li, H.-Y.; Wen, L.-J.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187-5189
56. Wu, W.; Su, W. J. Am. Chem. Soc. 2011, 133, 11924-11927
57. Wu, J.-C.; Song, R.-J.; Wang, Z.-Q.; Huang, X.-C.; Xie, Y.-X.; Li, J.-H. Angew Chem., Int. Ed. 2012, 51, 3453-3457
58. He, T.; Li, H.; Li, P.; Wang, L. Chem. Commun. 2011, 47, 8946-8948
59. Liu, Y.-K.; Lou, S.-J.; Xu, D.-Q.; Xu, Z.-Y. Chem.-Eur. J. 2010, 16, 13590-13593
60. Goswami, S.; Maity, A. C.; Fun, H.-K.; Chantrapromma, S. Eur. J. Org. Chem. 2009, 1417-1426
61. Huang, H.; Chen, Q.; Ku, X.; Meng, L.; Lin, L.; Wang, X.; Zhu, C.; Wang, Y.; Chen, Z.; Li, M.; Jiang, H.; Chen, K.; Ding, J.; Liu, H. J. Med. Chem. 2010, 53, 3048-3064
62. Sebastian, M.; Arun, V.; Robinson, P. P.; Leeju, P.; Varghese, D.; Varsha, G.; Yusuff, K. K. M. J. Coord. Chem. 2010, 63, 307-314
63. Sibbald, P. A.; Michael, F. E. Org. Lett. 2009, 11, 1147-1149
64. Albéniz, A. C.; Espinet, P.; López-Fernández, R.; Sen, A. J. Am. Chem. Soc. 2002, 124, 11278-11279
65. Walling, C. In Active Oxygen in Chemistry; Foote, C. S.; Valentine, J. S.; Greenberg, A.; Liebman, J. F., Eds.; Blackie: London, 1995; pp 24-65.
66. Jungkamp, T. P. W.; Seinfeld, J. H. Chem. Phys. Lett. 1996, 263, 371-378
67. 8, see: Ledwith, A.; Russell, P. J.; Sutcliffe, L. H. J. Chem. Soc. D, Chem. Commun. 1971, 964-965
68. Minisci, F. Synthesis 1973, 1-24
69. Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79-96
70. Minisci, F.; Vismara, A.; Morini, G.; Fontana, F.; Levi, S.; Serravalle, M. J. Org. Chem. 1986, 51, 476-479
71. Seiple, I. B.; Su, S.; Rodriguez, R. A.; Gianatassio, R.; Fujiwara, Y.; Sobel, A. L.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 13194-13196
72. Giordano, C.; Minisci, F.; Vismara, E.; Levi, S. J. Org. Chem. 1986, 51, 536
73. Rodrigo, M. R. C.; Reisler, H. J. Chem. Phys. 2012, 136, 084305
74. Das, B.; Venkateswarlu, K.; Suneel, K.; Majhi, A. Tetrahedron Lett. 2007, 48, 5371-5374
75. Kajigaeshi, S.; Kakinami, T.; Okamoto, T.; Fujsaki, S. Bull. Chem. Soc. Jpn. 1987, 60, 1159-60
76. Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896-1897
77. Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V.; Forood, B.; Flatt, B.; Nakai, H. J. Heterocyclic Chem. 2000, 37, 1655-1658
78. Munirajasekhar, D.; Himaja, M.; Sunil, V. M. Int. Res. J. Pharm. 2011, 2, 114-117
79. Leese, C. L. J. Chem. Soc.(Resumed) 1955, 303-309
80. Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2009, 131, 1372-1373
81. Zeynizadeh, B.; Behyar, T. Bull. Chem. Soc. Jpn. 2005, 78, 307
82. Kang, P.; Bobyr, E.; Dustman, J.; Hodgson, K. O.; Hedman, B.; Solomon, E. I.; Stack, T. D. P. Inorg. Chem. 2010, 49, 11030