An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea-hydrogen peroxide adduct, catalyzed by molecular iodine

Tetrahedron

Volumn 64, Issue 24, 2008, Pages 5649-5656

  Filipan Litvić, Mirela ^a   Litvić, Mladen ^a   Vinković, Vladimir ^b  

^a BELUPO Pharmaceuticals   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

1,4 Dihydropyridines; Aromatization; Catalytic; Iodine; Urea hydrogen peroxide adduct

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; ACETIC ACID; ACETIC ACID ETHYL ESTER; ALKYL GROUP; CYTOCHROME P450; FREE RADICAL; FUNCTIONAL GROUP; HYDROGEN PEROXIDE; IODINE; LORAZEPAM; OXAZEPAM; PERBORATE SODIUM; PERCARBONATE SODIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM IODATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SODIUM DERIVATIVE; SOLVENT; TRIFLUOROACETIC ACID; UREA;

ACETYLATION; AROMATIZATION; ARTICLE; BIOLOGY; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DERIVATIZATION; ELECTRON TRANSPORT; ELIMINATION REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERIZATION; METABOLISM; MOLECULAR DYNAMICS; MOLECULAR WEIGHT; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STOICHIOMETRY; SYNTHESIS; THERMOREGULATION;

EID: 43449132077     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.040     Document Type: Article

References (102)

1. Berkels B., Roesen R., Dhein S., Fricke U., and Klaus W. Cardiovasc. Drug Rev. 17 (1999) 179-186
2. Grün G., and Fleckenstein A. Arzneim.-Forsch. (Drug Res.) 22 (1972) 334-344
3. Bossert F., Meyer H., and Wehinger E. Angew. Chem. 93 (1981) 755-763
4. Janis R.A., and Triggle D.J. J. Med. Chem. 26 (1983) 775-785
5. Bischhoff H., Angerbauer R., Bender J., Bischoff E., Faggiotto A., Petzinna D., Pfitzner J., Porter M.C., Schmidt D., and Thomas G. Atherosclerosis 135 (1997) 119-130
6. Tsuruo T., Iida H., Nojiri M., Tsukagoshi S., and Sakurai Y. Cancer Res. 43 (1983) 2905-2910
7. Chapman R.W., Danko G., and Siegels M.I. Pharmacology 29 (1984) 282-291
8. Malaise W.J., and Mathias P.C.F. Diabetologia 28 (1985) 153-156
9. Krauze A., Germane S., Eberlins O., Sturms I., Klusa V., and Duburs G. Eur. J. Med. Chem. 34 (1999) 301-310
10. Peri R., Padmanabhan S., Singh S., Rutledge A., and Triggle D.J. J. Med. Chem. 43 (2000) 2906-2914
11. Zhou X., Zhang L., Tseng E., Scott-Ramsay E., Schentag J.J., Coburn R.A., and Morris M.E. Drug Metab. Dispos. 33 (2005) 321-328
12. Böcker R.H., and Guengerich F.P. J. Med. Chem. 28 (1986) 1596-1603
13. Kudo S., Okumura H., Miyamoto G., and Ishizaki T. Drug Metab. Dispos. 27 (1999) 303-308
14. The Merck Index. 13th ed. (2001), Merck Research Laboratories, New Jersey, NJ 6370
15. Mohr E., and Schneider W. J. Prakt. Chem. 69 (1904) 245-264
16. Kröhnke F., Ahrenhok G.M., and Gross K.F. J. Prakt. Chem. 11 (1960) 256-264
17. Görlitzer K., and Buß D. Arch. Pharm. (Weinheim, Ger.) 314 (1981) 949-954
18. Zolfigol M.A., Kiany-Borazjani M., Sadeghi M.M., Memarian H.R., and Mohammadpoor-Baltork I. Synth. Commun. 30 (2000) 2945-2950
19. Zolfigol M.A., Kiany-Borazjani M., Sadeghi M.M., Mohammadpoor-Baltork I., and Memarian H.R. Synth. Commun. 30 (2000) 3919-3923
20. Zolfigol M.A., Kiany-Borazjani M., Sadeghi M.M., Mohammadpoor-Baltork I., and Memarian H.R. Synth. Commun. 30 (2000) 551-558
21. Niknam K., Zolfigol M.A., Razavian S.M., and Mohammadpoor-Baltork I. Heterocycles 65 (2005) 657-660
22. Zolfigol M.A., Shirini F., Choghamarani A.G., and Mohammadpoor-Baltork I. Phosphorus Sulfur Silicon 178 (2003) 1709-1715
23. Zolfigol M.A., Choghamarani A.G., Dialameh S., Sadeghi M.M., Mohammadpoor-Baltork I., and Memarian H.R. J. Chem. Res. (2003) 18-20
24. Hashemi M.M., Ghafuri H., and Karimi-Jaberi Z. Monatsch. Chem. 134 (2006) 197-200
25. Zolfigol M.A., Bagherzadeh M., Niknam K., Shirini F., Mohammadpoor-Baltork I., Choghamarani A.G., and Baghbanzadeh M. J. Iran. Chem. Soc. 3 (2006) 73-80
26. Niknam K., Zolfigol M.A., Razavian S.M., and Mohammadpoor-Baltork I. J. Heterocycl. Chem. 43 (2006) 199-202
27. Itoh T., Nagata K., Matsuya Y., Miyazaki M., and Ohsawa A. J. Org. Chem. 62 (1997) 3582-3585
28. Zhu X.Q., Zhao B.J., and Cheng J.P. J. Org. Chem. 65 (2000) 8158-8163
29. Zolfigol M.A., Zebarjadian M.H., Sadegh M.M., Mohammadpoor-Baltork I., Memarian H.R., and Shamsipur M. Synth. Commun. 31 (2001) 929-934
30. Mashraqui S.H., and Karnik M.A. Synthesis (1998) 713-714
31. Khadilkar B., and Borkar S. Synth. Commun. 28 (1998) 207-212
32. Pfister J.R. Synthesis (1990) 689-690
33. Sabitha G., Kiran Kumar Reddy G.S., Reddy Ch.S., Fatima N., and Yadav J.S. Synthesis (2003) 1267-1271
34. Balogh M., Hermecz I., Mészáros Z., and Laszlo P. Helv. Chim. Acta 67 (1984) 2270-2272
35. Meyer H., Wehinger E., Bossert F., and Scherling D. Arzneim.-Forsch. (Drug. Res.) 33 (1983) 106-112
36. Sadeghi M.M., Mohammadpoor-Baltork I., Memarian H.R., and Sobhani S. Synth. Commun. 30 (2000) 1661-1665
37. Vanden Eynde J.J., Mayence A., and Maquestiau A. Tetrahedron 48 (1992) 463-468
38. Wang B., Hu Y., and Hu H. Synth. Commun. 29 (1999) 4193-4199
39. Zolfigol M.A., Sadeghi M.M., Mohammadpoor-Baltork I., Choghamarani A.G., and Taqian-Nasab A. Asian J. Chem. 13 (2001) 887-890
40. Zolfigol M.A., Salehi P., Ghorbani-Choghamarani A., Safaiee M., and Shahamirian M. Synth. Commun. 37 (2007) 1817-1823
41. Ko K.J., and Kim J.Y. Tetrahedron Lett. 40 (1999) 3207-3208
42. Vanden Eynde J.J., D'Ozario R., and Van Haverbeke Y. Tetrahedron 50 (1994) 2479-2484
43. Choudary B.M., Valli V.L.K., and Durga Prasad A. Synth. Commun. 21 (1991) 2007-2013
44. Kamal A., Ahmad M., Mohd N., and Hamid A.M. Bull. Chem. Soc. Jpn. 37 (1964) 610-612
45. Vanden Eynde J.J., Delfosse F., Mayence A., and Van Haverbeke Y. Tetrahedron 51 (1995) 6511-6516
46. Bagley M.C., and Lubinu M.C. Synthesis (2006) 1283-1288
47. Varma R.S., and Kumar D. Tetrahedron Lett. 40 (1999) 21-24
48. Kametani T., Ogasawara K., and Kozuka A. J. Pharm. Soc. Jpn. 86 (1966) 815-822
49. Hashemi M.M., Zakeri M.S., and Arianfar S. Iran. J. Chem. Chem. Eng. 22 (2003) 9-11
50. Momeni A.R., Massah A.R., Naghash H.J., Aliyan H., Solati S., and Sameh T. J. Chem. Res., Synop. 4 (2005) 227-228
51. Jain S.M., Kant R., Dhar K.L., Singh S., and Singh G.B. Ind. J. Chem. 29B (1990) 277-279
52. Litvić M., Cepanec I., Filipan M., Kos K., Bartolinčić A., Drušković V., Tibi M.M., and Vinković V. Heterocycles 65 (2005) 23-35
53. Memarian H.R., Mohammadpoor-Baltork I., Sadeghi M.M., and Samani Z.S. Ind. J. Chem. 40B (2001) 727-728
54. Comins D.L., and O'Connor S. Adv. Heterocycl. Chem. 44 (1988) 199-267
55. Varma R.S., and Kumar D. J. Chem. Soc., Perkin Trans. 1 (1999) 1755-1757
56. Gangadhar N., Kumar Ch.H., and Krupadanam G.L.D. Ind. J. Chem. 38B (1999) 87-89
57. Memarian H.R., Sadeghi M.M., and Momeni A.R. Ind. J. Chem. 38B (1999) 800-804
58. Memarian H.R., Sadeghi M.M., and Aliyan H. Ind. J. Chem. 37B (1998) 219-223
59. Zeynizadeh B., Dilmaghani K.A., and Roozijoy A. J. Chin. Chem. Soc. 52 (2005) 1001-1004
60. Yadav J.S., Reddy B.S., Sabitha G., and Reddy G.S.K.K. Synthesis (2000) 1532-1534
61. Cheng D.-P., and Chen Z.-C. Synth. Commun. 32 (2002) 793-798
62. Lee J.-W., and Ko K.-Y. Bull. Korean Chem. Soc. 25 (2004) 19-20
63. Lee K.-H., and Ko K.-Y. Bull. Korean Chem. Soc. 23 (2002) 1505-1506
64. Heravi M.M., Dirkwand F., Oskooie H.A., and Ghassemzadeh M. Heterocycl. Commun. 11 (2005) 75-78
65. Yadav J.S., Reddy B.V.S., Basak A.K., Baishya G., and Venkat Narsaiah A. Synthesis (2006) 451-454
66. Chai L., Zhao Y., Sheng Q., and Liu Z.-Q. Tetrahedron Lett. (2006) 9283-9285
67. Ortiz M.E., Núñez-Vergara L.J., and Squella J.A. Pharm. Res. 20 (2003) 292-296
68. Ortiz M.E., Núñez-Vergara L.J., Camargo C., and Squella J.A. Pharm. Res. 21 (2004) 428-435
69. Cai X.-h., Yang H.-j., and Zhang G.-l. Can. J. Chem. 83 (2005) 273-275
70. Panchgalle S.P., Choudhary S.M., Chavan S.P., and Kalkote U.R. J. Chem. Res., Synop. (2004) 550-551
71. Mao Y.-Z., Jin M.-Z., Liu Z.-L., and Wu L.-M. Org. Lett. 2 (2000) 741-742
72. Zolfigol M.A., Choghamarani A.G., Shahamirian M., Safaiee M., Mohammadpoor-Baltork I., Mallakpour S., and Abdollahi-Alibeik M. Tetrahedron Lett. (2005) 5581-5584
73. Anniyappan M., Muralidharan D., and Perumal T. Tetrahedron 58 (2002) 5069-5073
74. Mashraqui S.H., and Karnik M.A. Tetrahedron Lett. 39 (1998) 4896-4898
75. Heravi M.M., Behbahani F.K., Oskooie H.A., and Shoar R.H. Tetrahedron Lett. 46 (2005) 2775-2777
76. Nakamichi N., Kawashita Y., and Hayashi M. Org. Lett. 4 (2002) 3955-3957
77. Misner R.E. Diss. Abstr. 29B (1969) 2817
78. Nakamichi N., Kawashita Y., and Hayashi M. Synthesis (2004) 1015-1020
79. Chavan S.P., Kharul R.K., Kalkote U.R., and Shivakumar I. Synth. Commun. 33 (2003) 1333-1340
80. Hashemi M.M., Ahmadibeni Y., and Ghafuri H. Monatsh. Chem. 134 (2003) 107-110
81. Nasr-Esfahani M., Moghadam M., Tangestaninejad S., and Mirkhani V. Bioorg. Med. Chem. Lett. 15 (2005) 3276-3278
82. Moghadam M., Nasr-Esfahani M., Tangestaninejad S., and Mirkhani V. Bioorg. Med. Chem. Lett. 16 (2006) 2026-2030
83. Moghadam M., Nasr-Esfahani M., Tangestaninejad S., Mirkhani V., and Zolfigol M.A. Can. J. Chem. 84 (2006) 1-4
84. Vanden Eynde J.J., and Mayence A. Molecules 8 (2003) 381-391
85. Heravi M.M., and Ghassemzadeh M. Phosphorus Sulfur Silicon 180 (2005) 347-351
86. Tajbakhsh M., Lakouraj M., and Khojasteh V. Phosphorus Sulfur Silicon 179 (2004) 463-468
87. Cepanec I., Litvić M., and Pogorelić I. Org. Process Res. Dev. 10 (2006) 1192-1198
88. Skulski L. Molecules 5 (2000) 1331-1371
89. Zielinska A., and Skulski L. Molecules 10 (2005) 1307-1317
90. Lulinski P., Kryska A., Sosnowski M., and Skulski L. Synthesis (2004) 441-445
91. Jander J. Pure Appl. Chem. 49 (1977) 67-73
92. Zard S.Z. Radical Reactions in Organic Synthesis (2003), Oxford Chemistry Masters, New York, NY
93. Čeković Z. J. Serb. Chem. Soc. 70 (2005) 287-318
94. Litvić M., Filipan M., Pogorelić I., and Cepanec I. Green Chem. 7 (2005) 771-774
95. Filipan-Litvić, M. Aromatization of 1,4-Dihydropyridine Derivatives. Doctoral Thesis, University of Zagreb, 2006; 190 pp;
96. Loev B., Goodman M.M., Snader K.M., Tedeschi R., and Macko E. J. Med. Chem. 17 (1974) 956-965
97. Meyer H., Bossert F., and Horstmann H. Liebigs Ann. Chem. (1977) 1888-1894
98. Phillips A.P. J. Am. Chem. Soc. 72 (1950) 2780
99. Filipan-Litvić M., Litvić M., Cepanec I., and Vinković V. Molecules 12 (2007) 2546-2558
100. Filipan-Litvić M., Litvić M., Cepanec I., and Vinković V. ARKIVOC xi (2008) 96-103
101. Litvić M., Cepanec I., and Vinković V. Heterocycl. Commun. 9 (2003) 385-390
102. Kröhnke F. Synthesis (1976) 1-24