Porphyrins with Exocyclic Rings. Part 8 [1], Synthesis of Nitrogen-15 and Carbon-13 Labeled 2,3:7,8:12,13:17,18-Tetrabutanoporphyrin [2,3]

Journal of Heterocyclic Chemistry

Volumn 34, Issue 1, 1997, Pages 273-278

  Chen, Shaohua ^a   Lash, Timothy D ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000918394     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340141     Document Type: Article

References (56)

1. Part 6: T. D. Lash and B. H. Novak, Angew. Chem., 107, 723 (1995); Angew. Chem., Int. Ed. Engl., 34, 683 (1995); Part 7: T. D. Lash and P. Chandrasekar, J. Am. Chem. Soc., 118, 8767 (1996).
2. Part 6: T. D. Lash and B. H. Novak, Angew. Chem., 107, 723 (1995); Angew. Chem., Int. Ed. Engl., 34, 683 (1995); Part 7: T. D. Lash and P. Chandrasekar, J. Am. Chem. Soc., 118, 8767 (1996).
3. Part 6: T. D. Lash and B. H. Novak, Angew. Chem., 107, 723 (1995); Angew. Chem., Int. Ed. Engl., 34, 683 (1995); Part 7: T. D. Lash and P. Chandrasekar, J. Am. Chem. Soc., 118, 8767 (1996).
4. Results taken, in part, from S. Chen, M. S. Thesis, Illinois State University, 1995.
5. Results presented, in part, at the 28th Great Lakes Regional American Chemical Society Meeting, La Crosse, Wisconsin, June 1995. S. Chen and T. D. Lash, Program and Abstracts, 126.
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14. 15N-etioporphyrin-1 by the cyclotetramerization of an acetoxymethylpyrrole has also been reported: M. Momenteau, J. Mispelter, B. Loock and J. M. Lhoste, Can. J. Chem., 56, 2598 (1978). However, this methodology was subsequently shown, in accord with previous observations, to give mixtures of all four etioporphyrin type isomers. See: K. M. Smith and F. Eivazi, J. Org. Chem., 44, 2591 (1979).
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31. T. D. Lash, R. P. Balasubramaniam, J. J. Catarelio, M. C. Johnson, D. A. May, Jr., K. A. Bladel, J. M. Feeley, M. C. Hoehner, T. G. Marron, T. H. Nguyen, T. J. Perun, Jr., D. M. Qirizon, C. M. Shiner and A. Watson, Energy Fuels, 4, 668 (1990).
32. [191 D. A. May, Jr. and T. D. Lash, J. Org. Chem., 57, 4820 (1992).
33. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
34. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
35. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
36. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
37. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
38. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
39. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
40. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
41. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
42. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
43. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
44. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
45. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
46. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
47. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
48. For related papers on the synthesis of geochemically significant porphyrins, see: [a] T. D. Lash, Org. Geochem., 14, 213 (1989); [b] T. D. Lash, Energy Fuels, 7, 166 (1993); [c] T. D. Lash, D. M. Quizon-Colquitt, C. M. Shiner, T. H. Nguyen and Z. Hu, Energy Fuels, 7, 172 (1993); [d] T. D. Lash, in Advances in Nitrogen Heterocycles, Vol 1, C. J. Moody, ed, JAI Press, 1995, pp 19-69; [e] T. D. Lash and T. J. Perun, Jr., Tetrahedron Letters, 28, 6265 (1987); [f] T. D. Lash, Tetrahedron Letters, 29, 6877 (1988); [g] T. D. Lash and M. C. Johnson, Tetrahedron Letters, 30, 5697 (1989); [h] T. D. Lash and R. P. Balasubramaniam, Tetrahedron Letters, 31, 7545 (1990); [i] T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski and R. P. Balasubramaniam, J. Org. Chem., 57, 4809 (1992); [J] T. D. Lash and J. J. Catarello, Tetrahedron, 49, 4159 (1993); [k] D. M. Quizon-Colquitt and T. D. Lash, J. Heterocyclic Chem., 30, 477 (1993); [l} T. D. Lash, T. H. Nguyen and Z. Hu, Synlett, 905 (1994); [m] Z. Hu and T. D. Lash, Synlett, 909 (1994); [n] T. D. Lash and T. J. Roper, Tetrahedron Letters, 35, 7715 (1994); [o] T. D. Lash and C. P. Denny, Tetrahedron, 51, 59 (1995); [p] T. D. Lash and B. H. Novak, Tetrahedron Letters, 36, 4381 (1995).
49. G. D. Hartman and L. M. Weinstock, Organic Synthesis, 59, 183 (1979).
50. Glycine can also be used to prepare substituted pyrrole-2-carboxylates using alternative methodologies; e.g.: T. D. Lash and M. C. Hoehner, J. Heterocyclic Chem., 28, 1671 (1991).
51. It should be noted that improved yields have been claimed in the "Barton-Zard" pyrrole synthesis when a phosphorus Superbase is used in place of 1,8-diazabicyclo[5.4.0]undec-7-ene, and it is likely that slightly improved results could be obtained under these conditions; see: J. Tang and J. G. Verkade, J. Org. Chem., 59, 7793 (1994).
52. K. M. Smith, in Porphyrins and Metalloporphyrins, K. M. Smith, ed, Elsevier, Amsterdam, 1975, pp 381-399.
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