Porphyrins with exocyclic rings. Part 10.1 Synthesis of meso,β- propanoporphyrins from 4,5,6,7-tetrahydro-1H-indoles

Tetrahedron

Volumn 54, Issue 3-4, 1998, Pages 359-374

  Lash, Timothy D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE; INDOLE DERIVATIVE; PORPHYRIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032518931     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10288-5     Document Type: Article

References (63)

1. 1. Part 7: Lash, T.D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767. Part 8: Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273. Part 9: Lash, T.D. J. Porphyrins Phthalocyanines 1997, 1, 29.
2. 1. Part 7: Lash, T.D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767. Part 8: Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273. Part 9: Lash, T.D. J. Porphyrins Phthalocyanines 1997, 1, 29.
3. 1. Part 7: Lash, T.D.; Chandrasekar, P. J. Am. Chem. Soc. 1996, 118, 8767. Part 8: Chen, S.; Lash, T.D. J. Heterocyclic Chem. 1997, 34, 273. Part 9: Lash, T.D. J. Porphyrins Phthalocyanines 1997, 1, 29.
4. 2. Treibs, A. Justus Liebigs Ann. Chem. 1934, 510, 42.
5. 3. Baker, E.W. J. Am. Chem. Soc. 1966, 88, 2311; Baker, E.W.; Yen, T.F.; Dickie, J.P.; Rhodes, R.E.; Clark, L.F. ibid., 1967, 89, 3631; Baker, E.W.; Palmer, S.E. In The Porphyrina, Ed. Dolphin, D.; 1978, Vol. 1, pp 486-552; Academic Press, New York.
6. 3. Baker, E.W. J. Am. Chem. Soc. 1966, 88, 2311; Baker, E.W.; Yen, T.F.; Dickie, J.P.; Rhodes, R.E.; Clark, L.F. ibid., 1967, 89, 3631; Baker, E.W.; Palmer, S.E. In The Porphyrina, Ed. Dolphin, D.; 1978, Vol. 1, pp 486-552; Academic Press, New York.
7. 3. Baker, E.W. J. Am. Chem. Soc. 1966, 88, 2311; Baker, E.W.; Yen, T.F.; Dickie, J.P.; Rhodes, R.E.; Clark, L.F. ibid., 1967, 89, 3631; Baker, E.W.; Palmer, S.E. In The Porphyrina, Ed. Dolphin, D.; 1978, Vol. 1, pp 486-552; Academic Press, New York.
8. 4. a. Filby, R.H.; Van Berkel, G.J. In Metal Complexes in Fossil Fuels, Geochemistry, Characterization, and Processing, Ed. Filby, R.H.; Branthaver, J.F.; American Chemical Society, Washington DC, 1987, pp 2-37;
9. b. Chicarelli, M.I.; Kaur, S.; Maxwell, J.R. ibid., pp 40-67;
10. c. Ocampo, R.; Callot, H.J.; Albrecht, P. ibid., pp 68-73.
11. 5. Callot, H.J. In The Chlorophylls. Scheer, H., Ed.; CRC Press, Boca Raton, 1991, pp 339-364.
12. 6. Wolff, G.A.; Murray, M.; Maxwell, J.R.; Hunter, B.K.; Sanders, J.K.M. J. Chem. Soc., Chem. Commun. 1983, 922; Fookes, C.J.R. Ibid., 1474.
13. 6. Wolff, G.A.; Murray, M.; Maxwell, J.R.; Hunter, B.K.; Sanders, J.K.M. J. Chem. Soc., Chem. Commun. 1983, 922; Fookes, C.J.R. Ibid., 1474.
14. 7. Chicarelli, M.I.; Wolff, G.A.; Murray, M.; Maxwell, J.R. Tetrahedron 1984, 40, 4033.
15. 8. Wolff, G.A.; Chicarelli, M.I.; Shaw, G.J.; Evershed, R.P.; Quirke, J.M.E.; Maxwell, J.R. Tetrahedron 1984, 40, 3777.
16. 9. See reference 4b.
17. 10. Lash, T.D. Org. Geochem. 1989, 14, 213.
18. 11. Prowse, W.G.; Maxwell, J.R. Geochim. Cosmochim. Acta 1989, 53, 3081.
19. 12. Lash, T.D.; Balasuhramaniam, R.P. Tetrahedron Lett. 1990, 31, 7545.
20. 13. Preliminary communication: Lash, T.D. Tetrahedron Lett. 1988, 29, 6877.
21. 14. Results presented, in part, at the 190th National Meeting of the American Chemical Society, Chicago, Illinois, Sept. 12, 1985 (Abstract: Lash, T.D.; Johnson, M.C. Book of Abstracts, ORGN 254); 20th Midwest Regional American Chemical Society Meeting, Southern Illinois University, Carbondale, Illinois, Nov. 7, 1985 (Abstract: Lash, T.D. Program and Abstracts, Paper No. 615); 191st National Meeting of the American Chemical Society, New York City, New York, April 13, 1986 (Abstract: Lash, T.D.; Johnson, M.C.; Balasubramaniam, R.P.; Bladel, K.A.; Perun, T.J., Jr. Book of Abstracts, ORGN 74).
22. 14. Results presented, in part, at the 190th National Meeting of the American Chemical Society, Chicago, Illinois, Sept. 12, 1985 (Abstract: Lash, T.D.; Johnson, M.C. Book of Abstracts, ORGN 254); 20th Midwest Regional American Chemical Society Meeting, Southern Illinois University, Carbondale, Illinois, Nov. 7, 1985 (Abstract: Lash, T.D. Program and Abstracts, Paper No. 615); 191st National Meeting of the American Chemical Society, New York City, New York, April 13, 1986 (Abstract: Lash, T.D.; Johnson, M.C.; Balasubramaniam, R.P.; Bladel, K.A.; Perun, T.J., Jr. Book of Abstracts, ORGN 74).
23. 14. Results presented, in part, at the 190th National Meeting of the American Chemical Society, Chicago, Illinois, Sept. 12, 1985 (Abstract: Lash, T.D.; Johnson, M.C. Book of Abstracts, ORGN 254); 20th Midwest Regional American Chemical Society Meeting, Southern Illinois University, Carbondale, Illinois, Nov. 7, 1985 (Abstract: Lash, T.D. Program and Abstracts, Paper No. 615); 191st National Meeting of the American Chemical Society, New York City, New York, April 13, 1986 (Abstract: Lash, T.D.; Johnson, M.C.; Balasubramaniam, R.P.; Bladel, K.A.; Perun, T.J., Jr. Book of Abstracts, ORGN 74).
24. 15. Lash, T.D.; Perun, T.J., Jr. Tetrahedron Lett. 1987, 28, 6265. Lash, T.D.; Johnson, M.C. Tetrahedron Lett. 1989, 30, 5697. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909.
25. 15. Lash, T.D.; Perun, T.J., Jr. Tetrahedron Lett. 1987, 28, 6265. Lash, T.D.; Johnson, M.C. Tetrahedron Lett. 1989, 30, 5697. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909.
26. 15. Lash, T.D.; Perun, T.J., Jr. Tetrahedron Lett. 1987, 28, 6265. Lash, T.D.; Johnson, M.C. Tetrahedron Lett. 1989, 30, 5697. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909.
27. 15. Lash, T.D.; Perun, T.J., Jr. Tetrahedron Lett. 1987, 28, 6265. Lash, T.D.; Johnson, M.C. Tetrahedron Lett. 1989, 30, 5697. Lash, T.D.; Nguyen, T.H.; Hu, Z. Synlett 1994, 905. Hu, Z.; Lash, T.D. Synlett 1994, 909.
28. 16. Lash, T.D.; Balasubramaniam, R.P.; Catarello, J.J.; Johnson, M.C.; May, D.A., Jr.; Bladel, K.A.; Feeley, J.M.; Hoehner, M.C.; Marron, T.G.; Nguyen, T.H.; Perun, T.J., Jr.; Quizon, D.M.; Shiner, C.M.; Watson, A. Energy Fuels, 1990, 4, 668.
29. 17. Lash, T.D.; Quizon-Colquitt, D.M.; Shiner, C.M.; Nguyen, T.H.; Hu, Z. Energy Fuels, 1993, 4, 668.
30. 18. Lash, T.D.; Catarello, J.J. Tetrahedron 1993, 49, 4159.
31. 19. Quizon-Colquitt, D.M.; Lash, T.D. J. Heterocyclic Chem. 1993, 30, 477.
32. 20. Lash, T.D. In Advances in Nitrogen Heterocycles: Moody, C.J., Ed.; JAI Press, 1995, Vol. 1, pp 19-51.
33. 21. These samples have proven to be valuable standards for resonance Raman studies: Rankin, J.G.; Czernuszcwicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.
34. 21. These samples have proven to be valuable standards for resonance Raman studies: Rankin, J.G.; Czernuszcwicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.
35. 21. These samples have proven to be valuable standards for resonance Raman studies: Rankin, J.G.; Czernuszcwicz, R.S.; Lash, T.D. Org. Geochem., 1995, 23, 419. Rankin, J.G.; Czernuszewicz, R.S.; Lash, T.D. Inorg. Chem., 1995, 34, 3025. Czernuszewicz, R.S.; Rankin, J.G.; Lash, T.D. Inorg. Chem., 1996, 35, 199.
36. 22. Fischer, H.; Treibs, A. Justus Liebigs Ann. Chem. 1928, 466, 188; Fischer, H.; Treibs, A.; Helberger, H. ibid., 243; Clezy, P.S.; Mirza, A.H.; Ravi, B.N.; van Thuc, L. Aust. J. Chem. 1984, 37, 143; Dixon, D.W.; Callahan, J.; Ghosh, S.B.; Hwang, Y.C.; Shirazi, A.; Tyler, A.W. Inorg. Chim. Acta 1986, 122, 31.
37. 22. Fischer, H.; Treibs, A. Justus Liebigs Ann. Chem. 1928, 466, 188; Fischer, H.; Treibs, A.; Helberger, H. ibid., 243; Clezy, P.S.; Mirza, A.H.; Ravi, B.N.; van Thuc, L. Aust. J. Chem. 1984, 37, 143; Dixon, D.W.; Callahan, J.; Ghosh, S.B.; Hwang, Y.C.; Shirazi, A.; Tyler, A.W. Inorg. Chim. Acta 1986, 122, 31.
38. 22. Fischer, H.; Treibs, A. Justus Liebigs Ann. Chem. 1928, 466, 188; Fischer, H.; Treibs, A.; Helberger, H. ibid., 243; Clezy, P.S.; Mirza, A.H.; Ravi, B.N.; van Thuc, L. Aust. J. Chem. 1984, 37, 143; Dixon, D.W.; Callahan, J.; Ghosh, S.B.; Hwang, Y.C.; Shirazi, A.; Tyler, A.W. Inorg. Chim. Acta 1986, 122, 31.
39. 22. Fischer, H.; Treibs, A. Justus Liebigs Ann. Chem. 1928, 466, 188; Fischer, H.; Treibs, A.; Helberger, H. ibid., 243; Clezy, P.S.; Mirza, A.H.; Ravi, B.N.; van Thuc, L. Aust. J. Chem. 1984, 37, 143; Dixon, D.W.; Callahan, J.; Ghosh, S.B.; Hwang, Y.C.; Shirazi, A.; Tyler, A.W. Inorg. Chim. Acta 1986, 122, 31.
40. 23. Clezy, P.S.; Prashar, J.K. Aust. J. Chem. 1990, 43, 825; Clezy, P.S.; Jenie, U.; Prashar, J.K. ibid., 839. See also references 12, 15-20.
41. 23. Clezy, P.S.; Prashar, J.K. Aust. J. Chem. 1990, 43, 825; Clezy, P.S.; Jenie, U.; Prashar, J.K. ibid., 839. See also references 12, 15-20.
42. 24. Lash, T.D.; Bladel, K.A.; Shiner, C.M.; Zajeski, D.L.; Balasubramaniam, R.P. J. Org. Chem. 1992, 57, 4809.
43. 25. Clezy, P.S.; Liepa, A.J. Austral. J. Chem. 1970, 23, 229.
44. 26. Paine, J.B., III; Dolphin, D. J. Org. Chem. 1985, 50, 5598. See also: May, D.A., Jr.; Lash, T.D. J. Org. Chem. 1992, 57, 4820
45. 27. Chong, R.; Clezy, P.S.; Liepa, A.J.; Nichol, A.W. Austr. J. Chem. 1969, 22, 229.
46. 28. Cavaleiro, J.A.S.; Rocha Gonsalves, A.M. d'A.; Kenner, G.W.; Smith, K.M. J. Chem. Soc., Perkin Trans. I 1974, 1771. Somewhat different conditions were used in the original "2 + 2" syntheses: Arsenault, G.P.; Bullock. E.; MacDonald, S.F. J. Am. Chem. Soc. 1960, 82, 4384.
47. 28. Cavaleiro, J.A.S.; Rocha Gonsalves, A.M. d'A.; Kenner, G.W.; Smith, K.M. J. Chem. Soc., Perkin Trans. I 1974, 1771. Somewhat different conditions were used in the original "2 + 2" syntheses: Arsenault, G.P.; Bullock. E.; MacDonald, S.F. J. Am. Chem. Soc. 1960, 82, 4384.
48. 29. Lash, T.D. J. Porphyrins Phthalocyanines 1997, 1, 29.
49. 30. Johnson, A.W.; Kay, I.T. J. Chem. Soc. 1961, 2418; Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176; Baptista de Almeida, J.A.P.; Kenner, G.W.; Rimmer, R.; Smith, K.M. Tetrahedron 1976, 32, 1793; Smith, K.M.; Craig, G.W. J. Org. Chem. 1983, 48, 4302.
50. 30. Johnson, A.W.; Kay, I.T. J. Chem. Soc. 1961, 2418; Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176; Baptista de Almeida, J.A.P.; Kenner, G.W.; Rimmer, R.; Smith, K.M. Tetrahedron 1976, 32, 1793; Smith, K.M.; Craig, G.W. J. Org. Chem. 1983, 48, 4302.
51. 30. Johnson, A.W.; Kay, I.T. J. Chem. Soc. 1961, 2418; Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176; Baptista de Almeida, J.A.P.; Kenner, G.W.; Rimmer, R.; Smith, K.M. Tetrahedron 1976, 32, 1793; Smith, K.M.; Craig, G.W. J. Org. Chem. 1983, 48, 4302.
52. 30. Johnson, A.W.; Kay, I.T. J. Chem. Soc. 1961, 2418; Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176; Baptista de Almeida, J.A.P.; Kenner, G.W.; Rimmer, R.; Smith, K.M. Tetrahedron 1976, 32, 1793; Smith, K.M.; Craig, G.W. J. Org. Chem. 1983, 48, 4302.
53. 31. Smith, K.M.; Minnetian, O.M. J. Chem. Soc., Perkin Trans. I 1986, 277.
54. 32. Dolphin, D.; Harris, R.L.N.; Huppatz, J.L.; Johnson, A.W.; Kay, I.T.; Leng, J. J. Chem. Soc. 1966, 98. Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176. Smith, K.M.; Minnetian, O.M. J. Org. Chem. 1985, 50, 2073.
55. 32. Dolphin, D.; Harris, R.L.N.; Huppatz, J.L.; Johnson, A.W.; Kay, I.T.; Leng, J. J. Chem. Soc. 1966, 98. Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176. Smith, K.M.; Minnetian, O.M. J. Org. Chem. 1985, 50, 2073.
56. 32. Dolphin, D.; Harris, R.L.N.; Huppatz, J.L.; Johnson, A.W.; Kay, I.T.; Leng, J. J. Chem. Soc. 1966, 98. Grigg, R.; Johnson, A.W.; Kenyon, R.; Math, V.B.; Richardson, K. J. Chem. Soc. (C) 1969, 176. Smith, K.M.; Minnetian, O.M. J. Org. Chem. 1985, 50, 2073.
57. 33. Laver, W.G.; Neuberger, A.; Scott, J.J. J. Chem. Soc. 1959, 1474. These authors also report a mp of 76-78°C for samples recrystallized from cyclohexane.
58. 34. Clezy, P.S.; Fookes, C.J.R.; Mirza, A.H. Aust. J. Chem. 1977, 30, 1337.
59. 35. Lash, T.D.; Bellettini, J.R.; Bastian, J.A.; Couch, K.B. Synthesis, 1994, 170.
60. 36. Martin, D.F.; Fernelius, W.C.; Shamma, M. J. Am. Chem. Soc. 1959, 81, 130.
61. 37. Lecas-Nawrocka, A.; Levisalles, J.; Mariacher, C.; Renko, Z.; Rose, E. Can. J. Chem. 1984, 62, 2054.
62. 38. Bullock, E.; Johnson, A.W.; Markham, E.; Shaw, K.B. J. Chem. Soc. 1958, 1430.
63. 39. Clezy, P.S.; Fookes, C.J.R.; Liepa, A.J. Aust. J. Chem. 1972, 25, 1979.