Facile and efficient aromatization of 1,4-dihydropyridines with M(NO 3)2·XH2O, TNCB, TBAP and HMTAI and preparation of deuterium labeled dehydronifedipine from nifedipine-d3

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 12, 2010, Pages 3664-3668

  Shaikh, Ajam C ^a   Chen, Chinpiao ^a  

^a NATIONAL DONG HWA UNIVERSITY   (Taiwan)

Author keywords

Aromatization; Hantzsch's 1,4 dihydropyridines; Hexamethylenetetramine iodine; Tetra n butylammonium periodate; Trinitratocerium bromate

Indexed keywords

1,4 DIHYDROPYRIDINE; ACETIC ACID; DEHYDRONIFEDIPINE; DEUTERIUM; METHANOL; NIFEDIPINE; NITRIC ACID DERIVATIVE; OXIDIZING AGENT;

AROMATIZATION; ARTICLE; DRUG METABOLISM; OXIDATION;

CALCIUM CHANNEL BLOCKERS; DEUTERIUM; DIHYDROPYRIDINES; HUMANS; METALS; METHENAMINE; NIFEDIPINE; NITRATES; QUATERNARY AMMONIUM COMPOUNDS; RADIOPHARMACEUTICALS; VASODILATOR AGENTS;

TETRA;

EID: 77954213886     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.096     Document Type: Article

References (124)

1. U. Eisner, and J. Kuthan Chem. Rev. 72 1972 1
2. D.M. Stout Chem. Rev. 82 1982 223 and references cited therein
3. R.A. Janis, and D.J. Triggle J. Med. Chem. 26 1983 775
4. M.F. Gordeev, D.V. Patel, and E.M. Gordon J. Org. Chem. 61 1996 924
5. F. Bossert, and W. Vater Med. Res. Rev. 9 1989 291
6. S.F. Flaim, and R. Zelis Fed. Proc. 40 1981 2877
7. J.L. Reid, P.A. Meredith, and F. Pasanisi J. Cardiovasc. Pharmacol. 7 1985 S18
8. F.R. Buhler, and W. Kiowski J. Hypertens. 5 1987 S3
9. D.J. Triggle, D.D. Lango, and R.A. Janis Med. Res. Rev. 9 1989 123
10. A.B. Baranda, R.M. Alonso, R.M. Jiménez, and W. Weinmann Forensic Sci. Int. 156 2006 23
11. R. Böcker, and F.P. Guengerich J. Med. Chem. 29 1986 1596
12. F.P. Guengerich, W.R. Brian, M. Iwasaki, M.A. Sari, C. Baarnhielm, and P. Berntsson J. Med. Chem. 34 1991 1838
13. B. Meunier Chem. Rev. 92 1992 1411
14. M. Sono, and M.P. Roach Chem. Rev. 96 1992 2841
15. D. Rampe, P.W. Hake, B. Borretzen, K.H. Holm, and L. Skattebol Eur. J. Med. Chem. 28 1993 259
16. Y. Satoh, K. Okumura, and Y. Shiokawa Chem. Pharm. Bull. 42 1994 950
17. K. Ohtaka, and M. Kajiwara J. Labelled Compd. Radiopharm. 46 2003 1177
18. U. Pleiss J. Labelled Compd. Radiopharm. 50 2007 818
19. N.M. Soldatov Bioorg. Chem. 17 1989 141
20. A. Demmer, S. Andreae, H. Thole, and B. Tümmler Eur. J. Biochem. 264 1999 800
21. V.P. Shevchenko, N.F. Myasoedov, N.M. Soldatov, G.J. Duburs, V.V. Kastron, and I.P. Skrastins J. Labelled Compd. Radiopharm. 27 1989 721
22. M. Taki, A. Kuniyasu, H. Nakayama, and Y. Kanaoka Chem. Pharm. Bull. 39 1991 1860
23. M. Iwanami, T. Shibanuma, M. Fujimoto, R. Kawai, K. Tamazawa, T. Takenaka, K. Takahashi, and M. Murakami Chem. Pharm. Bull. 27 1979 1426
24. H. Arima, K. Tamazawa, and M. Takeuchi J. Labelled Compd. Radiopharm. 25 1987 161
25. Y.-Z. Xu, and C. Chen J. Labelled Compd. Radiopharm. 49 2006 897
26. Y.-Z. Xu, and C. Chen J. Labelled Compd. Radiopharm. 49 2006 1187
27. Y.-Z. Xu, H.-R. Lin, C.-A. Lua, and C. Chen J. Chin. Chem. Soc. 54 2007 493
28. A.C. Shaikh, Y.-Y. Wang, and C. Chen J. Labelled Compd. Radiopharm. 50 2007 660
29. Y.-J. Chen, and C. Chen J. Labelled Compd. Radiopharm. 50 2007 1143
30. Y.-Y. Wang, and C. Chen J. Chin. Chem. Soc. 54 2007 1363
31. Y.-Y. Wang, and C. Chen J. Labelled Compd. Radiopharm. 50 2007 1262
32. A.C. Shaikh, and C. Chen J. Labelled. Comp. Radiopharm. 51 2008 72
33. Z.-Y. You, Y.-J. Chen, Y.-Y. Wang, and C. Chen J. Chin. Chem. Soc. 55 2008 663
34. Y.-Z. Xu, H.-R. Lin, A.-C. Lua, and C. Chen J. Serb. Chem. Soc. 73 2008 1223
35. S. Srimurugan, K. Murugan, and C. Chen Chem. Pharm. Bull. 57 2009 1421
36. J.S. Yadav, B.V.S. Reddy, G. Sabitha, and G.S.K.K. Reddy Synthesis 11 2000 1532
37. J.-J.V. Eynde, R. D'Orazio, and Y. Van Haverbeke Tetrahedron 50 1994 2479
38. S.P. Phanchgalle, S.M. Choudhary, S.P. Chavan, and U.R. Kalkote J. Chem. Res. 2004 550
39. X. Cai, H. Yang, and G. Zhang Can. J. Chem. 83 2005 273
40. B. Zeynizadeh, K.A. Dilmaghani, and A. Roozijoy Synth. Commun. 35 2005 557
41. K.-Y. Ko, and J.-Y. Kim Tetrahedron Lett. 40 1999 3207
42. M. Litvic, I. Cepanec, M. Filipan, K. Kos, A. Bartolincic, V. Druskovic, M.M. Tibi, and V. Vinkovic Heterocycles 65 2005 23
43. R.S. Varma, and D. Kumar Tetrahedron Lett. 40 1999 21
44. G. Gelbard, J. Lin, and N. Roques J. Org. Chem. 57 1992 1789
45. M.M. Hashemi, Y. Ahmadibeni, and H. Ghafuri Monatsh. Chem. 134 2003 107
46. B. Karami, M. Montazerozohori, and M. Nasr-Esfahani Heterocycles 65 2005 2181
47. S.P. Chavan, U.R. Kalkote, I. Shivakumar, and R.K. Kharul Synth. Commun. 33 2003 1333
48. S.H. Mashraqui, and M.A. Kamik Tetrahedron Lett. 39 1998 4895
49. J.-J.V. Eynde, A. Mayence, and A. Maquestiau Tetrahedron 48 1992 463
50. M.M. Sadeghi, I.M. Baltork, H.R. Memarian, and S. Sobhani Synth. Commun. 30 2000 1661
51. A. Maquestiau, A. Mayence, and J.-J.V. Eynde Tetrahedron Lett. 32 1991 3839
52. B. Zeynizadeh, K.A. Dilmaghani, and A. Roozijoy J. Chin. Chem. Soc. 52 2005 1001
53. K. Niknam, M.A. Zolfigol, S.M. Razavian, and I.M. Baltork Heterocycles 65 2005 657
54. M.A. Zolfigol, M.M. Sadeghi, I.M. Baltork, A.G. Choghamarani, and A. Taqian-Nasab Asian J. Chem. 13 2001 887
55. M.M. Heravi, F. Derikvand, H.A. Oskooie, and R.H. Shoar Synth. Commun. 36 2006 77
56. M.A. Zolfigol, A. Ghorbani Choghamarani, S. Dialameh, M.M. Sadeghi, I. Mohammadpoor-Baltork, and H.R. Memarian J. Chem. Res. (S) 2003 19
57. M.A. Zolfigol, F. Shirin, A.G. Choghamarani, and I.M. Baltork Phosphorus, Sulfur Silicon Relat. Elem. 178 2003 1709
58. A.R. Momeni, T. Sameh, H. Golmohammadi, H.J. Naghash, H. Aliyan, A.R. Massah, and S. Solati Bull. Korean Chem. Soc. 27 2006 355
59. Y.Z. Mao, M.Z. Jin, Z.L. Liu, and L.M. Wu Org. Lett. 2 2000 741
60. M.A. Zolfigol, A.G. Choghamarani, M. Shahamirian, M. Safaiee, I.M. Baltork, S. Mallakpour, and M.A. Alibeik Tetrahedron Lett. 46 2005 5581
61. T. Itoh, K. Nagata, M. Okada, and A. Ohsawa Tetrahedron Lett. 36 1995 2269
62. T. Itoh, K. Nagata, Y. Matsuya, M. Miyazaki, and A. Ohsawa J. Org. Chem. 62 1997 3582
63. M.A. Zolfigol, M.H. Zebarjadian, M.M. Sadeghi, I. Mohammadpoor-Baltork, H.R. Memarian, and M. Shamsipur Synth. Commun. 31 2001 929
64. U.M. Dzhemilev, A.Z. Yakupova, S.K. Minsker, and G.A. Tolstikov Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 27 1978 585
65. N. Nakamichi, Y. Kawashita, and M. Hayashi Org. Lett. 4 2002 3955
66. M. Anniyappan, D. Muralidharan, and P.T. Perumal Tetrahedron 58 2002 5069
67. M. Nasr-Esfahani, M. Moghadam, and G. Valipour J. Iran. Chem. Soc. 5 2008 244
68. H. Adibi, and A.R. Hajipour Bioorg. Med. Chem. Lett. 17 2007 1008
69. R.S. Varma, and D. Kumar J. Chem. Soc., Perkin Trans. 1 1999 1755
70. D.P. Cheng, and Z.C. Chen Synth. Commun. 32 2002 793
71. J.W. Lee, and K.Y. Ko Bull. Korean Chem. Soc. 25 2004 19
72. N.N. Karade, S.V. Gampawar, J.M. Kondre, and S.V. Shinde ARKIVOC xii 2008 9
73. K.-H. Lee, and K.-Y. Ko Bull. Korean Chem. Soc. 23 2002 1505
74. L. Chai, Y. Zhao, Q. Sheng, and Z.Q. Liu Tetrahedron Lett. 47 2006 9283
75. Org. Synth. Coll. 2 1943 214
76. K. Tsuda, Y. Satch, N. Ikekawa, and H. Mishima J. Org. Chem. 21 1956 800
77. A. Kuno, Y. Sugiyama, K. Katsuta, T. Takenaka, and M. Murakami Chem. Pharm. Bull. 40 1992 1452
78. B. Loev, and K.M. Snader J. Org. Chem. 30 1965 1914
79. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, H.R. Memarian, and I. Mohammadpoor-Baltork J. Chem. Res. (S) 2000 167
80. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, H.R. Memarian, and I. Mohammadpoor-Baltork Synth. Commun. 30 2000 2945
81. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, I. Mohammadpoor-Baltork, and H.R. Memarian Synth. Commun. 30 2000 3919
82. M.A. Zolfigol, F. Shirin, A. Ghorbani Choghamarani, and I. Mohammadpoor-Baltork Green Chem. 4 2002 562
83. M.A. Zolfigol, M. Kiany-Borazjani, M.M. Sadeghi, I. Mohammadpoor-Baltork, and H.R. Memarian Synth. Commun. 30 2000 551
84. M.M. Heravi, K. Bakhtiari, H.A. Oskooie, and R. Hekmatshoar Russ. J. Org. Chem. 43 2007 1408
85. G. Sabitha, G.S.K.K. Reddy, C.S. Reddy, N. Fatima, and J.S. Yadav Synthesis 2003 1267
86. M. Balogh, I. Hermecz, Z. Meszaros, and P. Laszlo Helv. Chim. Acta 67 1984 2270
87. M.A. Zolfigol, M. Bagherzadeh, K. Niknam, F. Shirind, I. Mohammadpoor-Baltore, A.G. Choghamarana, and M. Baghbanzadeh J. Iran. Chem. Soc. 3 2006 73
88. M. Nasr-Esfahani, M. Moghadam, S. Tangestaninejad, V. Mirkhanib, and A.R. Momenic Bioorg. Med. Chem. 14 2006 2720
89. M. Nasr-Esfahani, M. Moghadam, S. Tangestaninejad, and V. Mirkhani Bioorg. Med. Chem. Lett. 15 2005 3276
90. M.M. Heravi, F.K. Behbahani, H.A. Oskooie, and R.H. Shoar Tetrahedron Lett. 46 2005 2775
91. S. Dehghanpour, M.M. Heravi, and F. Derikvand Molecules 12 2007 433
92. F.P. Guengrich, and R.H. Bocker J. Biol. Chem. 263 1998 8168
93. F. Pragst, B. Kaltofen, J. Volke, and J. Kuthan J. Electroanal. Chem. 119 1981 301
94. C. López-Alarcón, L.J. Núñez-Vergara, and J.A. Squella Electrochim. Acta 48 2003 2505
95. M.A. Khalilzadeh, A. Hosseini, H. Sadeghifar, and P. Valipour Acta Chim. Slov. 54 2007 900
96. O. Mitsunobu, S. Matsumoto, M. Wada, and H. Masuda Bull. Chem. Soc. Jpn. 45 1972 1453
97. M.Z. Jin, L. Yang, L.M. Wu, Y.C. Liu, and Z.L. Liu Chem. Commun. 1998 2451
98. M. Wang, Z.-G. Song, H. Gong, and H. Jiang Monatsh. Chem. 140 2009 177
99. R.S. Varma, and R. Dahiya Tetrahedron Lett. 39 1998 1307
100. Y.-G. Suh, B.-A. Koo, J.-A. Ko, and Y.-S. Cho Chem. Lett. 22 1993 1907
101. B.M. Choudary, M.L. Kantam, B. Kavita, C.V. Reddy, K.K. Rao, and F. Figueras Tetrahedron Lett. 39 1998 3555
102. S. Sun, N. Tsubaki, and K. Fujimoto Appl. Catal., A 202 2000 121
103. http://en.wikipedia.org/wiki/Vitamin-B12.
104. P. Selvam, S.K. Mohapatra, S.U. Sonavane, and R.V. Jayaram Tetrahedron Lett. 45 2004 2003
105. H. Firouzabadi, and N. Iranpoor Synth. Commun. 13 1983 1143
106. F. Shirini, H. Tajik, A. Aliakbar, and A. Akbar Synth. Commun. 31 2001 767 and references cited therein
107. F. Shirini, M. Esm-Hosseini, and Z. Hejazi Synth. Commun. 35 2005 2913
108. H. Tajik, F. Shirini, O.R. Farahkah, M.M. Lakouraj, and I.M. Baltork Russ. J. Org. Chem. 38 2002 1384
109. R. Santaiello, A. Manzocchi, and C. Farachi Synthesis 1980 563
110. Comer, W.; Lane, R. U.S. Patent 4120,877, 1979
111. Chem. Abstr. 90, 54802q.
112. R. Santaniello, F. Ponti, and A. Manzocchi Tetrahedron Lett. 21 1980 2655
113. S. David, and A. Thiéffry Tetrahedron Lett. 22 1981 2885
114. M.M. Heravi, A.J. Sabaghiani, M. Bakavoli, M. Ghassemzadeh, and K. Bakhtiari J. Chin. Chem. Soc. 54 2007 123
115. M.M. Heravi, N. Abdolhosseini, and H.A. Oskooie Tetrahedron Lett. 46 2005 8959
116. B.P. Bandgar, S.B. Admane, and S.S. Jare J. Chem. Res. (S) 1998 154
117. H. Gangwani, P.K. Sharma, and K.K. Banerji J. Chem. Res. (S) 1999 180
118. We have tested number of solvents such as benzene, dichloromethane, acetonitrile and acetic acid/water.
119. M.M. Awachat, A.C. Shaikh, N.V. Ganjave, S.P. Chavan, I. Shivakumar, and U.R. Kalkote J. Chem. Res. 2007 193
120. A. Sausins, and G. Duburs Heterocycles 27 1988 291
121. J.-J.V. Eynde, F. Delfosse, A. Mayence, and Y.V. Haverbeke Tetrahedron 51 1995 6511
122. H. Pritzkow Acta Crystallogr., Sect. B 31 1975 1589
123. A. Maquestiau, A. Mayence, and J.J. Vanden Eynde Tetrahedron Lett. 32 1991 3839
124. 4, and concentrated under reduced pressure to obtain crude product which was further purified by silica gel column chromatography using ethyl acetate-hexanes as mobile phase yielded corresponding pyridine. General procedure for oxidation of Hantzsch's 1,4-DHPs (1g) by HMTAI in methanol: An HMTAI (167 mg, 0.26 mmol) was added to the solution of 1,4-DHP (1g) (50 mg, 0.13 mmol) in 7.0 mL methanol and it was heated at reflux for given time. After completion of reaction, reaction mixture was cooled down to rt and filtered through short Celite pad. Methanol was removed under reduced pressure to obtain crude product which was further purified by silica gel column using ethyl acetate-hexane as mobile phase yielded corresponding pyridine.