Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl) formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents

Tetrahedron

Volumn 69, Issue 4, 2013, Pages 1378-1386

  Chang, Chun Hsi ^a   Tsai, Henry J ^b   Huang, Yu Ying ^a   Lin, Hui Yi ^a   Wang, Li Ya ^a   Wu, Tian Shung ^a   Wong, Fung Fuh ^a  

^a CHINA MEDICAL UNIVERSITY   (Taiwan)

^b ASIA UNIVERSITY   (Taiwan)

Author keywords

5 Aminopyrazoles; Formamide; Formamidine; Pyrazolo 3,4 d pyrimidine; Vilsmeier reaction

Indexed keywords

5 AMINO 1 (2 QUINOLINYL) 3 PHENYLPYRAZOLE; 5 AMINOPYRAZOLE DERIVATIVE; FORMAMIDE DERIVATIVE; HALOMETHYLENIMINIUM DERIVATIVE; N (1H PYRAZOL 5 YL)FORMAMIDE; N (1H PYRAZOL 5 YL)FORMAMIDINE DERIVATIVE; N METHYLFORMAMIDE; N' (1 PHENYL 3 TERT BUTYL 1H PYRAZOL 5 YL) N METHYLMETHANIMIDAMIDE; N' (1,3 DIPHENYL 1H PYRAZOL 5 YL) N METHYLMETHANIMIDAMIDE; N' [1 (2 PYRIDINYL) 3 (4 CHLOROPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 PYRIDINYL) 3 (4 METHOXYPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 PYRIDINYL) 3 (4 METHYLPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 PYRIDINYL) 3 PHENYL 1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 PYRIDINYL) 3 TERT BUTYL 1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 QUINOLINYL) 3 (4 CHLOROPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 QUINOLINYL) 3 (4 METHOXYPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 QUINOLINYL) 3 (4 METHYLPHENYL)1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 QUINOLINYL) 3 PHENYL 1H PYRAZOL 5 YL]FORMAMIDE; N' [1 (2 QUINOLINYL) 3 TESRT BUTYL 1H PYRAZOL 5 YL]FORMAMIDE; N' [1 PHENYL 3 (4 CHLOROPHENYL)1H PYRAZOL 5 YL] N METHYLMETHANIMIDAMIDE; N' [1 PHENYL 3 (4 METHOXYPHENYL)1H PYRAZOL 5 YL] N METHYLMETHANIMIDAMIDE; N' [1 PHENYL 3 (4 METHYLPHENYL)1H PYRAZOL 5 YL] N METHYLMETHANIMIDAMIDE; N1 (2 PYRIDINYL) 5 AMINOPYRAZOLE DERIVATIVE; N1 (2 QUINOLINYL) 5 AMINOPYRAZOLE DERIVATIVE; N1 PHENYL 5 AMINOPYRAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; VILSMEIER REAGENT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; VILSMEIER REACTION;

EID: 84871964522     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.11.002     Document Type: Article

References (75)

1. A. Vilsmeier, and A. Haack Ber. Dtsch. Chem. Ges. 60 1927 119 122
2. G. Jones, and S.P. Stanforth L.A. Paquette, Organic Reactions Vol. 49 1997 Wiley New York, NY 1 330
3. I.M. Downie, M.J. Earle, H. Heaney, and K.F. Shuhaibar Tetrahedron 49 1993 4015 4034
4. A. Lilienkampf, M.P. Johansson, and K. Wahala Org. Lett. 5 2003 3387 3390
5. X.-Y. Tang, and M. Shi J. Org. Chem. 73 2008 8317 8320
6. P.T. Perumal Indian J. Heterocycl. Chem. 11 2001 1 8
7. W. Pan, D.-W. Dong, and Q. Liu Org. Lett. 9 2007 2421 2423
8. K.-W. Wang, D.-X. Xiang, and D.-W. Dong Org. Lett. 10 2008 1691 1694
9. G. Jones, and S.P. Stanforth Org. React. 56 2000 355 659
10. C.M. Marson Tetrahedron 48 1992 3659 3726
11. L. Chen, Y.-L. Zhao, Q. Liu, C. Cheng, and C.-R. Piao J. Org. Chem. 72 2007 9259 9263
12. R. Zhang, D. Zhang, Y. Guo, G. Zhou, Z. Jiang, and D. Dong J. Org. Chem. 73 2008 9504 9507
13. P.G.M. Wuts, J.M. Northuis, and T.A. Kwan J. Org. Chem. 65 2000 9223 9225
14. D. Xiang, Y. Yang, R. Zhang, Y. Liang, W. Pan, J. Huang, and D.D. Dong J. Org. Chem. 72 2007 8593 8596
15. P.K. Mahata, C. Venkatesh, U.K. Syam Kumar, H. Ila, and H. Junjappa J. Org. Chem. 68 2003 3966 3975
16. S. Sivaprasad, R. Sridhar, and P.T. Perumal J. Heterocycl. Chem. 43 2006 389 394
17. K.H. Kumar, and P.T. Perumal Chem. Lett. 34 2005 1346 1347
18. H.K. Kumar, S. Selvi, and P.T. Perumal J. Chem. Res. 2004 218 219
19. R. Sridhar, and P.T. Perumal Synth. Commun. 33 2003 1483 1488
20. S. Selvi, and P.T. Perumal Indian J. Chem., Sect. B 41B 2002 1887 1893
21. S. Selvi, and P.T. Perumal Synth. Commun. 31 2001 2199 2202
22. R.R. Amaresh, and P.T. Perumal Synth. Commun. 30 2000 2269 2274
23. S. Selvi, and P.T. Perumal Synth. Commun. 30 2000 3925 3928
24. S. Selvi, and P.T. Perumal Indian J. Chem., Sect. B 39B 2000 163 165
25. R.R. Amaresh, and P.T. Perumal Tetrahedron 55 1999 8083 8094
26. P.T. Perumal, V.J. Majo, and R.V. Anand Indian J. Chem., Sect. B 38 1999 763 765
27. R.R. Amaresh, and P.T. Perumal Tetrahedron 54 1998 14327 14340
28. R.R. Amaresh, and P.T. Perumal Tetrahedron Lett. 39 1998 3837 3840
29. V.J. Majo, and P.T. Perumal J. Org. Chem. 63 1998 7136 7142
30. S. Selvi, and P.T. Perumal Tetrahedron Lett. 38 1997 6263 6266
31. V.J. Majo, and P.T. Perumal Tetrahedron Lett. 38 1997 6889 6892
32. V.J. Majo, and P.T. Perumal Tetrahedron Lett. 37 1996 5015 5018
33. B. Balasundaram, M. Venugopal, and P.T. Perumal Tetrahedron Lett. 34 1993 4249 4252
34. J.P. Michael Nat. Prod. Rep. 14 1997 605 618
35. S. Akila, S. Selvi, and K. Balasubramanian Tetrahedron 57 2001 3465 3469
36. M. Balasubramanian, and J.G. Keay A.R. Kartritzky, C.W. Ress, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 5 1996 Pergamor Oxford 245 Chapter 5.06
37. E. Campaigne, and W.L. Archer J. Am. Chem. Soc. 75 1953 989 996
38. W. Treihs, H.J. Neupert, and J. Hiebsch Chem. Ber. 92 1959 141 145
39. M. Damodiran, N. Panneer, S. Paramasivan, and T. Perumal Tetrahedron Lett. 50 2009 5474 5478
40. V.J. Häufel, and E. Breitmaier Angew. Chem. 86 1974 671 672
41. H.J. Mason, X. Wu, R. Schmitt, J.E. Macor, and G. Yu Tetrahedron Lett. 42 2001 8931 8934
42. P.A. Procopiou, A.C. Brodie, M.J. Deal, and D.F. Hayman Tetrahedron Lett. 34 1993 7483 7486
43. P.A. Procopiou, A.C. Brodie, M.J. Deal, and D.F. Hayman J. Chem. Soc., Perkin Trans. 1 1996 2249 2253
44. M. Zaoral, and Z. Arnold Tetrahedron Lett. 1 1960 9 13
45. H. Eilingsfeld, M. Seefelder, and H. Weidinger Angew. Chem. 72 1960 836 841
46. D.R. Hepburn, and H.R. Hudson J. Chem. Soc., Perkin Trans. 1 1976 754 762
47. A.G.M. Barrett, D.C. Braddock, R.A. James, N. Koike, and P.A. Procopiou J. Org. Chem. 63 1998 6273 6279
48. A.G.M. Barrett, N. Koike, and P.A. Procopiou J. Chem. Soc., Chem. Commun. 1995 1403 1412
49. Y. Kawano, N. Kaneko, and T. Mukaiyama Chem. Lett. 34 2005 1612 1618
50. A.G.M. Barrett, D.C. Braddock, R.A. James, and A. Procopiou Chem. Commun. 1997 433 438
51. J. Elguero A.R. Katritzky, C.W. Rees, K.T. Potts, Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon Oxford 167
52. J. Elguero A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 3 1996 Pergamon Oxford 1
53. A.N. Kost, and I.I. Grandberg A.R. Katritzky, A.J. Boulton, Advances in Heterocyclic Chemistry Vol. 6 1966 Academic New York 347
54. K.Y. Lee, J.M. Kim, and J.N. Kim Tetrahedron Lett. 44 2003 6737 6740 and references therein
55. S.M. Sakya, and B. Rast Tetrahedron Lett. 44 2003 7629 7632 and references therein
56. Y.R. Huang, and J.A. Katzenellenbogen Org. Lett. 2 2000 2833 2836 and references therein
57. N. Nishigaki Bioorg. Med. Chem. Lett. 13 2003 2985 2988
58. M.E.F. Braibante, H.T.S. Braibante, J.K. da Roza, and D.M. Henriques Synthesis 2003 1160 1162
59. S. Schenone, O. Bruno, A. Ranise, F. Bondavalli, M. D'Amico, W. Filippelli, G. Falcone, and V. De Novellis Il Farmaco 50 1995 179 182
60. Cooper, C. B.; Helal, C. J.; Sanner, M. A.; Wagner, T. T. PCT WO 18346 A1, 2002.
61. J.E. Ansel, L. El Kaim, A. Gadras, L. Grimaud, and N.K. Jana Tetrahedron Lett. 43 2002 8319 8321
62. V. Atlan, C. Buron, and L. Elkaim Synlett 2000 489 490
63. F. Palacios, D. Aparicio, and J.M. de los Santos Tetrahedron 52 1996 4123 4132
64. M. Moreno-Manãs, R.M. Sebastián, A. Vallribera, and F. Carini Synthesis 1999 157 160
65. R.M. Abdel-Rahman, M. Seada, M. Fawzy, and I. El-Baz Pharmazie 49 1994 729 733
66. D.S. Dodd, and R.L. Martinez Tetrahedron Lett. 45 2004 4265 4267
67. K.-M. Cheng, Y.-Y. Huang, J.-J. Huang, K. Kaneko, M. Kimura, H. Takayama, S.-H. Juang, and F.F. Wong Bioorg. Med. Chem. Lett. 20 2010 6781 6784
68. K.-S. Wen, H.-Y. Lin, Y.-Y. Huang, K. Kaneko, H. Takayama, M. Kimura, S.-H. Juang, and F.F. Wong Med. Chem. Res. 21 2012 3920 3928
69. Y. Luo, P. Zhong, X.H. Zhang, Q.L. Lin, and Y.N. Chen Chin. Chem. Lett. 19 2008 383 386
70. M.N. Jachak, A.B. Avhale, C.D. Tantak, and R.B. Toche J. Heterocycl. Chem. 42 2005 1311 1319
71. G. Jones, and S.P. Stanforth Org. React. 49 1997 1 330
72. O. Meth-Cohn, and S.P. Stanforth B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 2 1991 Pergamor Oxford 777 794
73. V. Srivastava, A.S. Negi, J.K. Kumar, and M.M. Gupta Steroids 71 2006 632 638
74. R.M. El-Shishtawy, and P. Almeida Tetrahedron 62 2006 7793 7798
75. M.N. Jachak, A.B. Avhale, V.J. Medhane, and R.B. Toche J. Heterocycl. Chem. 43 2006 1169 1175