Concise synthesis of multisubstituted isoquinolines from pyridines by regioselective diels-alder reactions of 2-silyl-3,4-pyridynes

Chemistry - A European Journal

Volumn 20, Issue 49, 2014, Pages 16228-16232

  Ikawa, Takashi ^a   Urata, Hirohito ^b   Fukumoto, Yutaka ^a   Sumii, Yuta ^a   Nishiyama, Tsuyoshi ^b   Akai, Shuji ^a  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Cycloaddition; Furans; Isoquinolines; Pyridynes; Silyl groups

Indexed keywords

AROMATIC COMPOUNDS; CYCLOADDITION; ORGANIC POLLUTANTS;

DIELS-ALDER REACTION; FUNCTIONAL GROUP TRANSFORMATIONS; FURANS; IPSO SUBSTITUTIONS; ISOQUINOLINES; PYRIDYNES; REGIOSELECTIVE SYNTHESIS; SILYL GROUP;

REGIOSELECTIVITY;

EID: 84915820661     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201404633     Document Type: Article

References (61)

1. Heterocycles in Natural Product Synthesis (Eds.: K. C. Majumdar, S. K. Chattopadhyay), Wiley-VCH, Weinheim, 2011.
2. a) T. C. Birdsall, G. S. Kelly, Altern. Med. Rev. 1997, 2, 94
3. b) M. Stiborová, J. Sejbal, L. Bořek-Dohalská, D. Aimová, J. Poljaková, K. Forsterová, M. Rupertová, J. Wiesner, J. Hudeček, M. Wiessler, E. Frei, Cancer Res. 2004, 64, 8374
4. c) J. K. Liu, W. T. Couldwell, Neurocrit. Care 2005, 2, 124.
5. Handbook of Heterocyclic Chemistry, 3edrd ed(Eds.: A. R. Katritzky, C. A. Ramsden, J. A. Joule, V. V. Zhdankin), Elsevier, Amsterdam, 2010.
6. W. M. Whaley, T. R. Govindachari, Organic Reactions Vol 6, John Wiley & Sons, New York, 1951, p. 74.
7. For recently reported syntheses of isoquinoline, see: a)CD. Gilmore, K. M. Allan, B. M. Stoltz, J. Am. Chem. Soc. 2008, 130, 1558
8. b) T. Iwayama, Y Sato, Chem. Commun. 2009, 5245
9. c) N. Guimond, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 12050
10. d) D. Yang, S. Burugupalli, D. Daniel, Y Chen, J. Org. Chem. 2012, 77, 4466
11. e) L. Zheng, J. Ju, Y Bin, R. Hua, J. Org. Chem. 2012, 77, 5794
12. f) B. S. Pilgrim, A. E. Gatland, C. T. McTernan, P. A. Procopiou, T.J. Donohoe, Org. Lett. 2013, 15, 6190
13. g) Z. Shi, D. C. Koester, M. Boultadakis-Arapinis, F. Glorius, J. Am. Chem. Soc. 2013, 135, 12204
14. h) Y-P. Zhu, M.-C. Liu, Q. Cai, F-C. Jia, A.-X. Wu, Chem. Eur. J. 2013, 19, 10132
15. i) K. Shekarrao, P.P. Kaishap, S. Gogoi, R. C. Boruah, RSC Adv. 2014, 4, 14013.
16. For selected DA reactions of 3,4-pyridynes and furans, see: a)T Kauffmann, F.-P. Boettcher, Chem. Ber. 1962, 95, 949
17. b) F. Effenberger, W. Daub, Chem. Ber. 1991, 124, 2119
18. c) M. Tsukazaki, V. Snieckus, Heterocycles 1992, 33, 533
19. d) M. T. Diaz, A. Cobas, E. Guitián, L. Castedo, Synlett 1998, 157
20. e) S. J. Connon, A. F Hegarty, J. Chem. Soc. Perkin Trans. 1 2000, 1245
21. f) M. Diaz, A. Cobas, E. Guitián, L. Castedo, Eur. J. Org. Chem. 2001, 4543
22. g) W. Lin, L. Chen, P. Knochel, Tetrahedron 2007, 63, 2787
23. h) M. F Enamorado, P. W. Ondachi, D. L Comins, Org. Lett. 2010, 12, 4513
24. i) A. E. Goetz, N. K. Garg, Nat. Chem. 2012, 5, 54.
25. For selected reports on 3,4-pyridynes, see: a) R. Levine, W. W. Leake, Science 1955, 121, 780
26. b) K. Vinter-Pasquier, B. Jamart-Grégoire, P. Caubère, Heterocycles 1997, 45, 2113
27. c) A. E. Goetz, S. M. Bronner, J. D. Cisneros, J. M. Melamed, R. S. Paton, K. N. Houk, N. K. Garg, Angew. Chem. Int. Ed. 2012, 51, 2758
28. Angew. Chem. 2012, 124, 2812
29. d) N. Saito, K.-i. Nakamura, S. Shibano, S. Ide, M. Minami, Y Sato, Org. Lett. 2013, 15, 386
30. e) A. E. Goetz, N. K. Garg, J. Org. Chem. 2014, 79, 846
31. f) N. Sato, K.i. Nakamura, Y Sato, Heterocycles 2014, 88, 929.
32. For recent reviews on arynes, see: a) H. Pellissier, M. Santelli, Tetrahedron 2003, 59, 701
33. b) H. H. Wenk, M. Winkler, W. Sander, Angew. Chem. Int. Ed. 2003, 42, 502
34. Angew. Chem. 2003, 115, 518
35. c) A. M. Dyke, A. J. Hester, G. C. Lloyd-Jones, Synthesis 2006, 4093
36. d) P. M. Tadross, B. M. Stoltz, Chem. Rev. 2012, 112, 3550.
37. For selected reports on silylbenzynes, see: a) T. Matsumoto, T. Sohma, S. Hatazaki, K. Suzuki, Synlett 1993, 843
38. b) C. Heiss, F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2005, 5236
39. c) S. Akai, T. Ikawa, S. Takayanagi, Y. Morikawa, S. Mohri, M. Tsubakiyama, M. Egi, Y. Wada, Y. Kita, Angew. Chem. Int. Ed. 2008, 47, 47
40. Angew. Chem. 2008, 120, 7787
41. d) V. Diemer, M. Begaud, F. R. Leroux, F. Colobert, Eur. J. Org. Chem. 2011, 341
42. e) T. Ikawa, T. Nishiyama, T. Shigeta, S. Mohri, S. Morita, S. Takayanagi, Y. Terauchi, Y. Morikawa, A. Takagi, Y. Ishikawa, S. Fujii, Y. Kita, S. Akai, Angew. Chem. Int. Ed. 2011, 50, 50
43. Angew. Chem. 2011, 123, 5792
44. f) S. M. Bronner, J. L. Mackey, K. N. Houk, N. K. Garg, J. Am. Chem. Soc. 2012, 134, 13966
45. g) T. Ikawa, A. Takagi, M. Goto, Y. Aoyama, Y. Ishikawa, Y. Itoh, S. Fujii, H. Tokiwa, S. Akai, J. Org. Chem. 2013, 78, 2965.
46. J. A. Crossley, J. D. Kirkham, D. L. Browne, J. P. A. Harrity, Tetrahedron Lett. 2010, 51, 6608.
47. We synthesized 3-bromo-2,4-bis(trimethylsilyl)pyridine; however, this compound was unstable.
48. C. J. Woltermann, J. A. Schwindeman, Fine Chem. 2002, 5.
49. The DA reaction of 2-(trimethylsilyl)-3,4-pyridyne with furan was reported, albeit in a low yield (42%), see Ref. [6b].
50. a) J. Duflos, G. Queguiner, J. Org. Chem. 1981, 46, 1195
51. b) J. R. Lennox, S. C. Turner, H. Rapoport, J. Org. Chem. 2001, 66, 7078.
52. For related ring opening of 5,8-epoxyisoquinolines, see: a) C. Bozzo, M. D. Pujol, Synlett 2000, 550
53. b) T. D. Nguyen, R. Webster, M. Lautens, Org. Lett. 2011, 13, 1370
54. c) J. Zhu, G. C. Tsui, M. Lautens, Angew. Chem. Int. Ed. 2012, 51, 51
55. Angew. Chem. 2012, 124, 12519.
56. a) M. Tsukazaki, V. Snieckus, Heterocycles 1993, 35, 689
57. b) P. Pierrat, P. Gros, Y. Fort, Org. Lett. 2005, 7, 697
58. c) K. Suzawa, M. Ueno, A. E. H. Wheatley, Y. Kondo, Chem. Commun. 2006, 4850.
59. For recent reports on the NBO analysis of benzynes, see: a) A. Takagi, T. Ikawa, Y. Kurita, K. Saito, K. Azechi, M. Egi, Y. Itoh, H. Tokiwa, Y. Kita, S. Akai, Tetrahedron 2013, 69, 4338
60. b) A. Takagi, T. Ikawa, K. Saito, S. Masuda, T. Ito, S. Akai, Org. Biomol. Chem. 2013, 11, 8145.
61. A. L. Allred, E. G. Rochow, J. Inorg. Nucl. Chem. 1958, 5, 264.