Facile assembly of 1-(4-haloisoquinolin-1-yl)ureas via a reaction of 2-alkynylbenzaldoxime, carbodiimide, and halide in water

Tetrahedron

Volumn 70, Issue 13, 2014, Pages 2246-2250

  Lai, Lifang ^a   Wang, Huanhuan ^b   Wu, Jie ^b,c  

^a CHANGZHOU UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1 (4 Haloisoquinolin 1 yl)urea; 2 Alkynylbenzaldoxime; Carbodiimide; Halide; Water

Indexed keywords

2 ALKYNYLBENZALDOXIME; ALDOXIME; CYANAMIDE; ELECTROPHILE; HALIDE; SODIUM IODIDE; UNCLASSIFIED DRUG; UREA DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; EVAPORATION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84896729522     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.02.026     Document Type: Article

References (68)

1. K.W. Bentley The Isoquinoline Alkaloids Vol. 1 1998 Harwood Academic Australia
2. B.W. Trotter, K.K. Nanda, N.R. Kett, C.P. Regan, J.J. Lynch, G.L. Stump, L. Kiss, J. Wang, R.H. Spencer, S.A. Kane, R.B. White, R. Zhang, K.D. Anderson, N.J. Liverton, C.J. McIntyre, D.C. Beshore, G.D. Hartman, and C.J. Dinsmore J. Med. Chem. 49 2006 6954
3. P. Ramesh, N.S. Reddy, and Y. Venkateswarlu J. Nat. Prod. 62 1999 780
4. C. Marchand, S. Antony, K.W. Kohn, M. Cushman, A. Ioanoviciu, B.L. Staker, A.B. Burgin, L. Stewart, and Y. Pommier Mol. Cancer Ther. 5 2006 287
5. J.D. Phillipson, M.F. Roberts, and M.H. Zenk The Chemistry and Biology of Isoquinoline Alkaloids 1985 Springer Berlin
6. V.G. Kartsev Med. Chem. Res. 13 2004 325
7. M.D. Menachery, G.L. Lavanier, M.L. Wetherly, H. Guinaudeau, and M. Shamma J. Nat. Prod. 49 1986 745
8. C. Pomeranz Monatsh. Chem. 14 1893 116
9. P. Fritsch Ber. 26 1893 419
10. A. Bischler, and B. Napieralski Ber. 26 1893 1903
11. A. Pictet, and T. Spengler Ber. 44 1911 2030
12. G.M. Coppola, and H.F. Schuster The Chemistry of Heterocyclic Compounds: Isoquinolines Vol. 38 1981 Wiley New York, NY Part 3
13. M.D. Rozwadowska Heterocycles 39 1994 903
14. Organic Reactions Vol. 6 1951 John Wiley & Sons London, UK Chapters 2-4
15. M. Balasubramanian, and J.G. Keay Isoquinoline Synthesis A.E. McKillop, A.R. Katrizky, C.W. Rees, E.F.V. Scrivem, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Elsevier Oxford, UK 245
16. M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341
17. Q. Huang, and R.C. Larock J. Org. Chem. 68 2003 980
18. G. Dai, and R.C. Larock J. Org. Chem. 68 2003 920
19. G. Dai, and R.C. Larock J. Org. Chem. 67 2002 7042
20. Q. Huang, J.A. Hunter, and R.C. Larock J. Org. Chem. 67 2002 3437
21. K.R. Roesch, and R.C. Larock J. Org. Chem. 67 2002 86
22. K.R. Roesch, H. Zhang, and R.C. Larock J. Org. Chem. 66 2001 8042
23. G. Dai, and R.C. Larock Org. Lett. 3 2001 4035
24. S. Obika, H. Kono, Y. Yasui, R. Yanada, and Y. Takemoto J. Org. Chem. 72 2007 4462
25. N. Asao, S.S. Yudha, T. Nogami, and Y. Yamamoto Angew. Chem., Int. Ed. 44 2005 5526
26. R. Yanada, S. Obika, H. Kono, and Y. Takemoto Angew. Chem., Int. Ed. 45 2006 3822
27. N. Asao, K. Iso, and S.S. Yudha Org. Lett. 8 2006 4149
28. A.B. Beeler, S. Su, C.A. Singleton, and J.A. Porco Jr. J. Am. Chem. Soc. 129 2007 1413
29. S. Mori, M. Uerdingen, N. Krause, and K. Morokuma Angew. Chem., Int. Ed. 44 2005 4715
30. Y.-N. Niu, Z.-Y. Yan, G.-L. Gao, H.-L. Wang, X.-Z. Shu, K.-G. Ji, and Y.-M. Liang J. Org. Chem. 74 2009 2893
31. Y.-Y. Yang, W.-G. Shou, Z.-B. Chen, D. Hong, and Y.-G. Wang J. Org. Chem. 73 2008 3928
32. D. Fischer, H. Tomeba, P.N. Kahadi, N.T. Patil, Z. Huo, and Y. Yamamoto J. Am. Chem. Soc. 130 2008 15720
33. M. Movassaghi, and M.D. Hill Org. Lett. 10 2008 3485
34. S. Su, and J.A. Porco Jr. Org. Lett. 9 2007 4983
35. T. Xu, and G. Liu Org. Lett. 14 2012 5416
36. C. Si, and A.G. Myers Angew. Chem., Int. Ed. 50 2011 10409
37. Q. Liu, Y. Wu, P. Chen, and G. Liu Org. Lett. 15 2013 6210
38. H. Ren, Y. Luo, S. Ye, and J. Wu Org. Lett. 13 2011 2552
39. S. Ye, H. Wang, and J. Wu Eur. J. Org. Chem. 2010 6436
40. S. Ye, H. Wang, and J. Wu ACS Comb. Sci. 13 2011 120
41. Q. Xiao, S. Ye, and J. Wu Org. Lett. 14 2012 3430
42. H. Wang, M. Zhu, S. Ye, and J. Wu RSC Adv. 3 2013 13626
43. H.-S. Yeom, S. Kim, and S. Shin Synlett 2008 924
44. Z. Huo, H. Tomeba, and Y. Yamamoto Tetrahedron Lett. 49 2008 5531
45. T.L. Ho, B. Gupta, and G.A. Olah Synthesis 1977 676
46. N.B. Barhate, A.S. Gajare, R.D. Wakharkar, and A.V. Bedekar Tetrahedron Lett. 39 1998 6349
47. N.B. Barhate, A.S. Gajare, R.D. Wakharkar, and A.V. Bedekar Tetrahedron 55 1999 11127
48. U. Bora, G. Bose, M.K. Chaudhuri, S.S. Dhar, R. Gopinath, A.T. Khan, and B.K. Patel Org. Lett. 2 2000 247
49. C. Ye, and J.M. Shreeve J. Org. Chem. 69 2004 8561
50. R.K. Dieter, L.E. Nice, and S.E. Velu Tetrahedron Lett. 37 1996 2377
51. K.-M. Kim, and I.-H. Park Synthesis 2004 2641
52. G.-W. Wang, and J. Gao Green Chem. 14 2012 1125
53. V. Nair, S.B. Panicker, A. Augustine, T.G. George, S. Thomas, and M. Vairamani Tetrahedron 57 2001 7417
54. S.C. Roy, C. Guin, K.K. Rana, and G. Maiti Tetrahedron Lett. 42 2001 6941
55. A. Subbarayappa, S. Ghosh, P.U. Patoliya, G. Ramachandraiah, M. Agrawal, M.R. Gandhi, S.C. Upadhyay, P.K. Ghosh, and B.C. Ranu Green Chem. 10 2008 232
56. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, and K. Miyamoto J. Am. Chem. Soc. 127 2005 12244
57. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, and Y. Kita Angew. Chem., Int. Ed. 44 2005 6193
58. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, and Y. Kita Chem. Commun. 2007 1224
59. A. Moroda, and H. Togo Synthesis 2008 1257
60. M. Uyanik, T. Yasui, and K. Ishihara Bioorg. Med. Chem. Lett. 19 2009 3848
61. A. RodrIguez, and W.J. Moran Org. Lett. 13 2011 2220
62. A. Yoshimura, K.R. Middleton, C. Zhu, V.N. Nemykin, and V.V. Zhdankin Angew. Chem., Int. Ed. 51 2012 8059
63. M. Uyanik, H. Okamoto, T. Yasui, and K. Ishihara Science 328 2010 1376
64. M. Uyanik, D. Suzuki, T. Yasui, and K. Ishihara Angew. Chem., Int. Ed. 50 2011 5331
65. M. Uyanik, and K. Ishihara ChemCatChem 4 2012 177
66. J. Xie, H. Jiang, Y. Cheng, and C. Zhu Chem. Commun. 2012 979
67. T. Froehr, C.P. Sindlinger, U. Kloeckner, P. Finkbeiner, and B.J. Nachtsheim Org. Lett. 13 2011 3754
68. A. Yoshimura, C. Zhu, K.R. Middleton, A.D. Todora, B.J. Kastern, A.V. Maskaev, and V.V. Zhdankin Chem. Commun. 2013 4800