Syntheses of type-I porphyrins via monopyrrole tetramerization

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7177-7180

  Nguyen, Liem T ^a   Smith, Kevin M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030607150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01632-2     Document Type: Article

References (21)

1. 1. (a) Nguyen, L. T.; Senge, M. O.; Smith, K. M. Tetrahedron Lett. 1994, 35, 7581.
2. (b) Nguyen, L. T.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1996, 61, 998.
3. 2. Boudif, A.; Momenteau, M. J. Chem. Soc., Chem. Commun. 1994, 2069.
4. 3. Lin, Y. N.; Lash, T. D. Tetrahedron Lett. 1995, 36, 9441.
5. 4. Sessler, J. L.; Genge, J. W.; Urbach, A.; Sanson, P. Synlett 1996, 1987.
6. 5. Smith, K. M. In "Porphyrins and Metalloporphyrins," (Smith, K. M., ed.); Elsevier: Amsterdam, 1975, p 5.
7. 6. (a) Bullock, E.; Johnson, A. W.; Markham, E.; Shaw, K. B. J. Chem. Soc. 1958, 1430.
8. (b) Momenteau, M.; Mispelter, J.; Loock, B.; Lhoste, J. M. Can. J. Chem. 1978, 56, 2598.
9. 7 (a) Kay, I. T. Proc. Natl. Acad. Sci. 1962, 48, 901.
10. (b) Smith, K. M.; Eivazi, F. J. Org. Chem. 1979, 44, 2591.
11. 8. Mauzerall, D. J. Am. Chem. Soc. 1960, 82, 2601.
12. 9. Smith, K. M. In "Porphyrins and Metalloporphyrins," (Smith, K. M., ed.); Elsevier: Amsterdam, 1975, p. 38.
13. 10. Chang, C. K.; Bag, N. J. Org. Chem. 1995, 60, 7030.
14. 11. Jeandon, C.; Callot, H. J. Bull. Soc. Chim. Fr. 1993, 48, 625.
15. 12. Cheng, L.; Ma, J. OPPI Briefs 1995, 27, 224.
16. 13. Pyrrole Mannich bases [2-(N,N-dimethylaminomethyl)pyrroles] have previously been used in porphyrin syntheses: Whitlock, H. W.; Hanauer, R. J. Org. Chem. 1968, 33, 2169. Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733.
17. 13. Pyrrole Mannich bases [2-(N,N-dimethylaminomethyl)pyrroles] have previously been used in porphyrin syntheses: Whitlock, H. W.; Hanauer, R. J. Org. Chem. 1968, 33, 2169. Eisner, U.; Lichtarowicz, A.; Linstead, R. P. J. Chem. Soc. 1957, 733.
18. 2Me), 3.67, 3.69 (each s, 12 H, Me and OMe), 10.08 (s, 4 H, meso-H).
19. 15. Fischer, H.; Orth, H. "Die Chemie des Pyrrols," Vol. 2, part 1; Akademische Verlag.: Leipzig, 1937, p. 483.
20. 16. Hudson, M. F.; Smith, K. M. J. Chem. Soc., Chem. Commun. 1973, 515. Hudson, M. F.; Smith, K. M. Tetrahedron 1975, 31, 3077.
21. 16. Hudson, M. F.; Smith, K. M. J. Chem. Soc., Chem. Commun. 1973, 515. Hudson, M. F.; Smith, K. M. Tetrahedron 1975, 31, 3077.