Porphyrins with exocyclic rings. Part 19: Efficient syntheses of phenanthrolinoporphyrins

Tetrahedron

Volumn 61, Issue 49, 2005, Pages 11601-11614

  Lash, Timothy D ^a   Lin, Yanning ^a   Novak, Bennett H ^a   Parikh, Mihir D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

'3+1' Methodology; MacDonald condensation; Phenanthroline; Porphyrins; Pyrroles

Indexed keywords

2 PROPANOL; ACETIC ACID; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; DICHLOROMETHANE; ESTER DERIVATIVE; ETHYLENE GLYCOL; PHENANTHRENE DERIVATIVE; PHENANTHROLINE DERIVATIVE; PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DILUTION; ELECTRON; OXIDATION; POLYMERIZATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE MEASUREMENT; ULTRAVIOLET SPECTROSCOPY;

EID: 27644548170     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.089     Document Type: Article

References (114)

1. T.D. Lash K.M. Kadish K.M. Smith R. Guilard The Porphyrin Handbook Vol. 2 2000 Academic San Diego 125 199
2. T.D. Lash J. Porphyrins Phthalocyanines 5 2001 267
3. T.D. Lash Energy Fuels 7 1993 166
4. T.F. Yen T.F. Yen The Role of Trace Metals in Petroleum 1975 Ann Arbor Science Ann Arbor 1 30
5. M.J. Crossley, and P.L. Burn J. Chem Soc., Chem. Commun. 1991 1569
6. M.J. Crossley, L.J. Govenlock, and J.K. Prashar J. Chem. Soc., Chem. Commun. 1995 2379
7. M.J. Crossley, and J.K. Prashar Tetrahedron Lett. 38 1997 6751
8. T.X. Lu, J.R. Reimers, M.J. Crossley, and N.S. Hush J. Phys. Chem. 98 1994 11878
9. L. Jaquinod, O. Siri, R.G. Khoury, and K.M. Smith Chem. Commun. 1998 1261
10. M.G.H. Vicente, M.T. Cancilla, C.B. Lebrilla, and K.M. Smith Chem. Commun. 1998 2355
11. P.S. Clezy, C.J.R. Fookes, and A.H. Mirza Aust. J. Chem. 30 1977 1337
12. P.S. Clezy, and A.H. Mirza Aust. J. Chem. 35 1982 197
13. P.S. Clezy, and C.W.F. Leung Aust. J. Chem. 46 1993 1705
14. D.A. May Jr., and T.D. Lash J. Org. Chem. 57 1992 4820
15. J.M. Boggess, R.S. Czernuszewicz, and T.D. Lash Org. Geochem. 33 2002 1111
16. R. Bonnett, and K.A. McManus J. Chem. Soc., Perkin Trans. 1 1996 2461
17. M.G.H. Vicente, A.C. Tome, A. Walter, and J.A.S. Cavaleiro Tetrahedron Lett. 38 1997 3639
18. M.G.H. Vicente, L. Jaquinod, R.G. Khoury, A.Y. Madrona, and K.M. Smith Tetrahedron Lett. 40 1999 8763
19. S. Ito, N. Ochi, T. Murashima, H. Uno, and N. Ono Heterocycles 52 2000 399
20. O.S. Finikova, A.V. Cheprakov, I.P. Beletskaya, P.J. Carroll, and S.A. Vinogradov J. Org. Chem. 69 2004 522 and references cited therein
21. S. Ito, N. Ochi, H. Uno, T. Murashima, and N. Ono Chem. Commun. 2000 893
22. O.S. Finikova, A.V. Cheprakov, P.J. Carroll, and S.A. Vinogradov J. Org. Chem. 68 2003 7517
23. O.S. Finikova, S.E. Aleshchenkov, R.P. Brinas, A.V. Cheprakov, P.J. Carroll, and S.A. Vinogradov J. Org. Chem. 70 2005 4617
24. T.D. Lash, and B.H. Novak Tetrahedron Lett. 36 1995 4381
25. T.D. Lash, and B.H. Novak Angew. Chem., Int. Ed. Engl. 34 1995 683
26. B.H. Novak, and T.D. Lash J. Org. Chem. 63 1998 3998
27. P. Chandrasekar, and T.D. Lash Tetrahedron Lett. 37 1996 4873
28. T.D. Lash, and P. Chandrasekar J. Am. Chem. Soc. 118 1996 8767
29. J.D. Spence, and T.D. Lash J. Org. Chem. 65 2000 1530
30. T.D. Lash, P. Chandrasekar, A.T. Osuma, S.T. Chaney, and J.D. Spence J. Org. Chem. 63 1998 8455
31. T.D. Lash, C. Wijesinghe, A.T. Osuma, and J.R. Patel Tetrahedron Lett. 38 1997 2031
32. T.D. Lash, T.M. Werner, M.L. Thompson, and J.M. Manley J. Org. Chem. 66 2001 3152
33. T.D. Lash, and V. Gandhi J. Org. Chem. 65 2000 8020
34. P.G. Sammes, and G. Yahioglu Chem. Soc. Rev. 23 1994 327
35. R.P. Thummel, and C.M. Chamchoumis C.J. Moody Advances in Nitrogen Heterocycles Vol. 4 2000 JAI Stamford, CT 107
36. Preliminary communication: Y. Lin, and T.D. Lash Tetrahedron Lett. 36 1995 9441
37. M.J. Crossley, P.L. Burn, S.J. Langford, and J.K. Prashar J. Chem. Soc., Chem. Commun. 1995 1921
38. These results were presented, in part, at the following meetings: 207th National Meeting of the American Chemical Society, San Diego, CA, March 1994
39. (Lash, T. D.; Roper, T. J.; Novak, B. H.; Lin, Y. Book of Abstracts, ORGN 154);
40. 27th Great Lakes/26th Central Joint Regional American Chemical Society Meeting, Ann Arbor, Michigan, June 1994
41. (Novak, B. H.; Lash, T.D. Program and Abstracts, Abstract No. 419);
42. 208th National Meeting of the American Chemical Society, Washington, DC, August 1994
43. (Novak, B. H.; Lash, T.D. Book of Abstracts, ORGN 222);
44. 209th National Meeting of the American Chemical Society, Anaheim, CA, April 1995
45. (Lash, T. D.; Novak, B. H.; Lin, Y.; Melquist, M. J.; Patel, J.R. Book of Abstracts, ORGN 177);
46. 28th Great Lakes Regional American Chemical Society Meeting, La Crosse, Wisconsin, June 1995
47. (Lin, Y.; Lash, T.D. Program and Abstracts, Abstract No. 125);
48. 210th National Meeting of the American Chemical Society, Chicago, Illinois, August 1995
49. (Lash, T. D.; Lin, Y. Book of Abstracts, ORGN 179).
50. (a) Novak, B.H. M.S. Thesis, Illinois State University, 1994.
51. (b) Lin, Y. M.S. Thesis, Illinois State University, 1995.
52. T.D. Lash, and C.P. Denny Tetrahedron 51 1995 59
53. See also: A.C. Tomé, P.S.S. Lacerdo, M.G.P.M.S. Neves, and J.A.S. Cavaleiro Chem. Commun. 1997 1199
54. D.H.R. Barton, and S.Z. Zard J. Chem. Soc., Chem. Commun. 1985 1098
55. D.H.R. Barton, J. Kervagoret, and S.Z. Zard Tetrahedron 46 1990 7587
56. T.D. Lash, J.R. Bellettini, J.A. Bastian, and K.B. Couch Synthesis 1994 170
57. M.A. Drinan, and T.D. Lash J. Heterocycl. Chem. 31 1994 255
58. S. Chen, and T.D. Lash J. Heterocycl. Chem. 34 1997 273
59. D.H. Burns, C.S. Jabara, and M.W. Burden Synth. Commun. 25 1995 379
60. N. Ono, H. Kawamura, and K. Maruyama Bull. Chem. Soc. Jpn. 62 1989 3386
61. N. Ono, H. Kawamura, M. Bougauchi, and K. Maruyama Tetrahedron 46 1990 7483
62. J.L. Sessler, A. Mozaffari, and M.R. Johnson Org. Synth. 70 1991 68
63. C. Bauder, R. Ocampo, and H.J. Callot Tetrahedron 48 1992 5135
64. D.P. Arnold, L. Burgess-Dean, J. Hubbard, and M.A. Rahman Aust. J. Chem. 47 1994 969
65. G. Haake, D. Struve, and F.-P. Montforts Tetrahedron Lett. 35 1994 9703
66. H. Dumoulin, S. Rault, and M. Robba J. Heterocycl. Chem. 33 1996 255
67. M. Adamczyk, and R.E. Reddy Tetrahedron 52 1996 14689
68. N. Bag, S.-S. Chern, S.-M. Peng, and C.K. Chang Tetrahedron Lett. 36 1995 6409
69. J. Tang, and J.G. Verkade J. Org. Chem. 59 1994 7793
70. T.D. Lash, B.H. Novak, and Y. Lin Tetrahedron Lett. 35 1994 2493
71. See also: T.D. Lash, M.L. Thompson, T.M. Werner, and J.D. Spence Synlett 2000 213
72. N. Ono, H. Hironaga, K. Simizu, K. Ono, K. Kuwano, and T. Ogawa J. Chem. Soc., Chem. Commun. 1994 1019
73. N. Ono, H. Hironaga, K. Ono, S. Kaneko, T. Murashima, T. Ueda, C. Tsukamura, and T. Ogawa J. Chem. Soc., Perkin Trans. 1 1996 417
74. For related studies, see: (c) E.T. Pelkey, and G.W. Gribble Synthesis 1999 1117
75. L. Jaquinod, C. Gros, M.M. Olmstead, M. Antolovich, and K.M. Smith Chem. Commun. 1996 1475
76. G.P. Arsenault, E. Bullock, and S.F. MacDonald J. Am. Chem. Soc. 82 1960 4384
77. J.A.S. Cavaleiro, A.M.d'A Rocha Gonsalves, G.W. Kenner, and K.M. Smith J. Chem. Soc., Perkin Trans. 1 1974 1771
78. T.D. Lash, and J.J. Catarello Tetrahedron 49 1993 4159
79. T.D. Lash Tetrahedron 54 1998 359
80. T.D. Lash Chem. Eur. J. 2 1996 1197
81. For recent reviews on porphyrin synthesis, see: (a) K.M. Smith K.M. Kadish K.M. Smith R. Guilard The Porphyrin Handbook Vol. 1 2000 Academic San Diego 1 43
82. K.M. Smith J. Porphyrins Phthalocyanines 4 2000 319 324
83. H. Sakurai, A. Shirahata, K. Sasaki, and A. Hosomi Synthesis 1979 740
84. T.D. Lash, S.T. Chaney, and D.T. Richter J. Org. Chem. 63 1998 9076
85. M.J. Broadhurst, R. Grigg, and A.W. Johnson J. Chem. Soc. (C) 1971 3681
86. J.L. Sessler, M.R. Johnson, and V. Lynch J. Org. Chem. 52 1987 4394
87. T.D. Lash J. Porphyrins Phthalocyanines 1 1997 29
88. D.H. Burns, D.C. Shi, and T.D. Lash Chem. Commun. 2000 299
89. A. Boudif, and M. Momenteau J. Chem. Soc., Chem. Commun. 1994 2069
90. A. Boudif, and M. Momenteau J. Chem. Soc., Perkin Trans. 1 1996 1235
91. J.L. Sessler, J.W. Genge, A. Urbach, and P. Sanson Synlett 1996 187
92. T.D. Lash Angew. Chem., Int. Ed. Engl. 34 1995 2533
93. T.D. Lash, and S.T. Chaney Chem. Eur. J. 2 1996 944
94. T.D. Lash, and S.T. Chaney Tetrahedron Lett. 37 1996 8825
95. T.D. Lash, M.J. Hayes, J.D. Spence, M.A. Muckey, G.M. Ferrence, and L.F. Szczepura J. Org. Chem. 67 2002 4860
96. T.D. Lash Synlett 2000 279 and references cited therein
97. T. Schönemeier, and E. Breitmaier Synthesis 1997 273
98. Waldo, M. L. 'Synthesis and characterization of 8,12,13,17-tetraethyl-7, 18-dimethyl-3,4-diazaporphyrin and bis-3,5-(2-pyrryl)-1,2,4-triazoles and their substituted analogs', MS Thesis, Michigan State University, 1998
99. R. Bohme, and E. Breitmaier Synthesis 1999 2096
100. S. Ito, T. Murashima, H. Uno, and N. Ono Chem. Commun. 1998 1661
101. D.H. Burns, Y.H. Li, D.C. Shi, and T.M. Caldwell J. Org. Chem. 67 2002 4536
102. D.T. Gryko, and M. Galezowski Org. Lett. 7 2005 1749
103. S.H. Lee, and K.M. Smith Tetrahedron Lett. 46 2005 2009
104. C. Tardieux, F. Bolze, C.P. Gros, and R. Guilard Synthesis 1998 267
105. L.T. Nguyen, M.O. Senge, and K.M. Smith Tetrahedron Lett. 35 1994 7581
106. L.T. Nguyen, M.O. Senge, and K.M. Smith J. Org. Chem. 61 1996 998
107. T.D. Lash, and T.J. Roper Tetrahedron Lett. 35 1994 7715
108. J.M. Manley, T.J. Roper, and T.D. Lash J. Org. Chem. 70 2005 874
109. G.D. Hartman, and L.M. Weinstock Org. Synth. 59 1979 183
110. G.F. Smith, and F.W. Cagle Jr. J. Org. Chem. 12 1947 781
111. P.J. Crook, A.H. Jackson, and G.W. Kenner J. Chem. Soc. (C) 1971 474
112. P.S. Clezy, R.J. Crowley, and T.T. Hai Aust. J. Chem. 35 1982 411
113. E. Bullock, A.W. Johnson, E. Markham, and K.B. Shaw J. Chem. Soc. 1958 1430
114. A.W. Johnson, I.T. Kay, E. Markham, R. Price, and K.B. Shaw J. Chem. Soc. 1959 3416