CAN-catalyzed regioselective synthesis of pyrido[2,3-c ]carbazoles by the Povarov reaction

Synthesis

Volumn 2012, Issue 2, 2012, Pages 253-258

  Viji, Mayavan ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

annulations; heterocycles; Lewis acids ; Povarov reaction; regioselectivity

Indexed keywords

ANNULATIONS; GOOD YIELD; HETEROCYCLES; LEWIS ACID; MILD REACTION CONDITIONS; POVAROV REACTION; REGIOSELECTIVE SYNTHESIS; VINYL ETHERS;

AMMONIUM COMPOUNDS; CATALYSIS; CERIUM; ETHERS; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

10 BROMO 7 BUTYL 3 METHYL 7H PYRIDO[2,3 C]CARBAZOLE; 10 CHLORO 3,7 DIMETHYL 7H PYRIDO[2,3 C]CARBAZOLE; 2 METHYL 11H PYRIDO[2,3 A]CARBAZOLE; 2,5,11 TRIMETHYL 6H PYRIDO[3,2 B]CARBAZOLE; 3 METHYL 7H PYRIDO[2,3 C]CARBAZOLE; 3,7 DIMETHYL 7H PYRIDO[2,3 C]CARBAZOLE; 6 ETHYL 2,5,11 TRIMETHYL 6H PYRIDO[3,2 B]CARBAZOLE; 7 BENZYL 3 METHYL 7H PYRIDO[2,3 C]CARBAZOLE; 7 BUTYL 8,10 DICHLORO 3 METHYL 7H PYRIDO[2,3 C]CARBAZOLE; 7 ETHYL 3 METHYL 7H PYRIDO[2,3 C]CARBAZOLE; AMMONIUM NITRATE; CARBAZOLE DERIVATIVE; CERIUM AMMONIUM NITRATE; ETHER DERIVATIVE; ETHYLVINYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; POVAROV REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 84855658156     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289967     Document Type: Article

References (104)

1. For reviews, see
2. Pindur U, Lemster T, Recent Res. Dev. Org. Bioorg. Chem. 1997 1 33
3. Kirsch G H., Curr. Org. Chem. 2001 5 507
4. Bergman J, Janosik T, Wahlstrom N, Adv. Heterocycl. Chem. 2001 80 1
5. Knölker H.-J, Reddy K R., Chem. Rev. 2002 102 4303
6. Fröhner W, Krahl M P., Reddy K R., Knölker H.-J, Heterocycles 2004 63 2393
7. Agarwal S, Cämmerer S, Filali S, Fröhner W, Knöll J, Krahl M P., Reddy K R., Knölker H.-J, Curr. Org. Chem. 2005 9 1601
8. Bellina F, Rossi R, Tetrahedron 2006 62 7213
9. Pindur U, Kim Y.-S, Mehrabani F, Curr. Med. Chem. 1999 6 29
10. Prudhomme M, Eur. J. Med. Chem. 2003 38 123
11. Lescot E, Muzard G, Markovits J, Belleney J, Roques B P., LePecq J B., J. Med. Chem. 1986 29 1731
12. Dalton L K., Demerac S, Teitei T, Aust. J. Chem. 1969 22 185
13. Peiaprat D, Oberlin R, LeGuen I, Roques B P., J. Med. Chem. 1980 23 1330
14. Lesca P, Lecointe P, Pelaprat D, Paoletti C, Mansuy D, Biochem. Pharmacol. 1980 29 3231
15. Léon P, Garbay-Jaureguiberry C, Barsi M C., LePecq J B., Roques B P., J. Med. Chem. 1987 30 2074
16. Moron J, Huel C, Bisagni E, Heterocycles 1993 36 2753
17. Goodwin S, Smith A F., Horning E C., J. Am. Chem. Soc. 1959 81 1903
18. Loder J W., Aust. J. Chem. 1966 19 1947
19. Kilminster K N., Sainsbury M, Webb B, Phytochemistry 1972 11 389
20. Ahond A, Fernandez H, Julia-Moore M, Poupat C, Sánchez V, Potier P, Kan S K., Sévenet T, J. Nat. Prod. 1981 44 193
21. Dalton L K., Demerac S, Elmes B C., Loder J W., Swan J M., Teitei T, Aust. J. Chem. 1967 20 2715
22. Svoboda G H., Poore G A., Montfort J, J. Pharm. Sci. 1968 57 1720
23. Sengupta S K., Cheng X C. C., In Cancer Chemotherapeutic Agents, ACS Professional Reference Books Foye W O. American Chemical Society Washington DC 1995 246-251
24. Paoletti C, LePecq J B., DatXuong N, Lesca P, Lecointe P, Curr. Chemother. 1978 2 1195
25. Juret P, Tanguy A, Girard A, LeTalaer J Y., Abbatucci J S., DatXuong N, LePecq J B., Paoletti C, Eur. J. Cancer 1978 14 205
26. LePecq J B., DatXuong N, Gosse C h, Paoletti C, Proc. Natl. Acad. Sci. U.S.A. 1974 71 5078
27. Auclair C, Voisin E, Banoun H, Paoletti C, Bernadou J, Meunier B, J. Med. Chem. 1984 27 1161
28. Jardine I, In Anticancer Agents Based on Natural Product Models Cassady J M. Douros J D. Academic Press New York 1980 319
29. Stiborová M, Breuer A, Aimová D, Stiborová- Rupertová M, Wiessler M, Frei E, Int. J. Cancer 2003 107 885
30. Sainsbury M, Synthesis 1977 437
31. May C, Moody C J., J. Chem. Soc., Perkin Trans. 1 1988 247
32. Suffness M, Cordell C A., In The Alkaloids Vol. 25 Brossi A Academic Press San Diego 1985 89-142
33. Gribble G W., In The Alkaloids Vol. 39 Brossi A Academic Press San Diego 1990 239-352
34. Gribble G W., In Advances in Heterocyclic Natural Product Synthesis Vol. 1 Pearson W H. JAI Press Greenwich 1990 43-94
35. Alvarez M, Joule J A., In The Chemistry of Heterocyclic Compounds Saxton J E. Wiley Chichester 1994 261-278
36. Boese R, VanSickele A P., Vollhardt K P. C., Synthesis 1994 1374
37. Blechert S, Knier R, Schroers H, Wirth T, Synthesis 1995 593
38. Miki Y, Tada Y, Yanase N, Hachiken H, Matsushita K, Tetrahedron Lett. 1996 37 7753
39. Jones R A., Pastor J, Siro J, Voro T N., Tetrahedron 1997 53 479
40. Haider H, Mereiter K, Wanko R, Heterocycles 1995 41 1445
41. Miki Y, Tada Y, Matsushita K, Heterocycles 1998 48 1593
42. Chaitanya T K., Nagarajan R, Org. Biomol. Chem. 2011 9 4662
43. Fujiwara A N., Acton E M., Goodman L, J. Med. Chem. 1967 10 126
44. May C, Moody C J., J. Chem. Soc., Chem. Commun. 1984 925
45. Saulnier M G., Gribble G W., J. Org. Chem. 1983 48 2690
46. Perche J.-C, Ruf S G., Buu-Hoï N P., J. Chem. Soc., Perkin Trans. 1 1972 2 260
47. Elmes B C., Swan J M., Aust. J. Chem. 1969 22 1963
48. Bergman J, Carlsson R, Tetrahedron Lett. 1978 19 4051
49. Gribble G W., Fletcher G L., Ketcha D M., Rojopadhya M, J. Org. Chem. 1989 54 3264
50. Kano S, Sugino E, Shibuya S, Hibino S, J. Org. Chem. 1981 46 2979
51. Gaddam V, Nagarajan R, Org. Lett. 2008 10 1975
52. Gaddam V, Nagarajan R, Tetrahedron Lett. 2009 50 1243
53. Gaddam V, Ramesh S, Nagarajan R, Tetrahedron 2010 66 4218
54. Daly J W., Spande T F., In Alkaloids: Chemical and Biological Perspectives Vol. 4 Pelletier S W. Wiley New York 1986 1-274
55. Foder G B., Colasanti B, In Alkaloids: Chemical and Biological Perspectives Vol. 3 Pelletier S W. Wiley New York 1985 1-90
56. Boger D L., Weinreb S M., Hetero Diels-Alder Methodology in Organic Synthesis Academic Press San Diego 1987 Chap. 2 34-70
57. Buomora P, Olsen J C., Oh T, Tetrahedron 2001 57 6099
58. For representative reviews and monographs, see:, Carruthers W, Cycloaddition Reactions in Organic Synthesis Pergamon Press Oxford 1990
59. Kumar A, Chem. Rev. 2001 101 1
60. Nicolaou K C., Snyder S A., Montagnon T, Vassilikogiannakis G, Angew. Chem. Int. Ed. 2002 41 1669
61. Tringuelli F, Taticchi A, The Diels-Alder Reaction. Selected Practical Methods John Wiley London 2002
62. Cycloaddition Reactions in Organic Synthesis Kobayashi S Jørgensen K A. Wiley-VCH New York 2002
63. Rinner U, Lentsch C, Aichinger C, Synthesis 2010 3763
64. Majumdar K C., Taher S, Ponra S, Synthesis 2010 4043
65. Majumdar K C., Ponra S, Ganal S, Synlett 2010 2575
66. Kouznetsov V V., Tetrahedron 2009 65 2721
67. Povarov L S., Russ. Chem. Rev. (Engl. Transl.) 1967 36 656
68. Povarov L S., Mikhailov B M., Izv. Akad. Nauk SSR., Ser. Khim. 1963 953
69. Waldmann H, Synlett 1995 133
70. Barluenga J, Joglar J, G onzalez F J., Fustero S, Synlett 1990 129
71. Kobayashi S, Eur. J. Org. Chem. 1999 15
72. Stevenson P J., Nieuwenhuyzen M, Osborne D, Chem. Commun. 2002 444
73. Babu G, Perumal P T., Aldrichimica Acta 2000 33 16
74. Waldmann H, Synthesis 1994 535
75. Behforouz M, Ahmadian M, Tetrahedron 2000 56 5259
76. Tietze L F., Kettschau G, Top. Curr. Chem. 1997 189 1
77. Vogt P F., Miller M J., Tetrahedron 1998 54 1317
78. Kametani T, Takeda H, Suzuki Y, Honda T, Synth. Commun. 1985 15 499
79. Ma Y, Qian C, Xie M, Sun J, J. Org. Chem. 1999 64 6462
80. Babu G, Perumal P T., Tetrahedron Lett. 1997 38 5025
81. Zhang J, Li C.-J, J. Org. Chem. 2002 67 3969
82. Kouznetsov V V., Astrudillosaavedra L, VargasMendez L Y., Ramirez M C., J. Chil. Chem. Soc. 2004 49 319
83. Maiti G, Kundu P, Tetrahedron Lett. 2006 47 5733
84. Boger D L., Weinreb S M., Hetero Diels-Alder Methodology in Organic Synthesis Academic Press San Diego 1987 9
85. Grieco P A., Bahasas A, Tetrahedron Lett. 1988 29 5855
86. Yadav J S., Reddy B V. S., Srinivas R, Madhuri C, Ramalingam T, Synlett 2001 240
87. Zhou F, Xu F, Han X, Zhou J, Shen Q, Eur. J. Org. Chem. 2007 5265
88. Semwal A, Nayak S, Synth. Commun. 2006 36 227
89. Sridharan V, Avendaño C, Menéndez J C., Synlett 2007 1079
90. Antoniotti S, Poulain-Martini S, Dunach E, Synlett 2010 2973
91. Nandi G C., Samal S, Singh M S., Synlett 2010 1133
92. For reviews on CAN-mediated reactions, see:, Ho T L., Synthesis 1973 347
93. Molander G A., Chem. Rev. 1992 92 29
94. Imamoto T, Lanthanide Reagents in Organic Synthesis Academic Press London 1994 119
95. Nair V, Mathew J, Prabhakaran J, Chem. Soc. Rev. 1997 127
96. Hwu J R., King K.-Y, Curr. Sci. 2001 81 1043
97. Nair V, Deepthi A, Chem. Rev. 2007 107 1862
98. Nair V, Panicker S B., Nair L G., George T G., Augustine A, Synlett 2003 156
99. Nair V, Balagopal L, Rajan R, Mathew J, Acc. Chem. Res. 2004 37 21
100. Encyclopedia of Reagents for Organic Synthesis 2nd ed., Vol. 3 Wiley New York 2009 2132-2139
101. Nair V, Deepthi A, Tetrahedron 2009 65 10745
102. Sridharan V, Menéndez J C., Chem. Rev. 2010 110 3805
103. Sridharan V, Avendaño C, Menéndez J C., Tetrahedron 2007 63 673
104. 2. Chemical formula weight is 322.39; orthorhombic; unit cell parameters: a =6.6003(8) Å, b =18.947(3) Å, c =27.539(4) Å, = = =90. Space group Pbca.