Regioselective pyrrole synthesis from asymmetric β-diketone and conversion to sterically hindered porphyrin

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1427-1430

  Fujii, Hiroshi ^a   Yoshimura, Tetsuhiko ^a   Kamada, Hitoshi ^a  

^a Yamagata Technopolis Foundation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584911     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00039-7     Document Type: Article

References (13)

1. 1. a) Jones, R. A.; Bean, G. P. The Chemistry of Pyrroles, Academic Press, London, 1977;
2. b) Schofield, K. Hetro-Aromatic Nitrogen Compounds, Pyrrole and Pyridines, Butterworth, London, 1967.
3. 2. Knorr, L. Justus, Liebigs Ann. Chem. 1886, 236, 290.
4. 3. Zanetti, C. U. and Levi, E. Gazz. Chim. Ital. 1894, 24, I, 546.
5. 4. Kleinspehn, G. G. J. Am. Chem. Soc. 1955, 77, 1546.
6. 5. Ono, N.; Kawamura, H.; Bougauchi, M.; Maruyama, K. Tetrahedron, 1990, 46, 7483.
7. 6. a) Fujii, H. J. Am. Chem. Soc. 1993, 115, 4641.
8. b) Fujii, H. Inorg. Chem. 1993, 32, 875.
9. 3. The pyrrole was extracted by ether and evaporation of the ether exatract furnished white pyrrole(6d).
10. + = 647.7 (cal = 647.5).
11. 9. (a) Paine III, J. B.; Kirsher, W. B.; Moskowitz, D. W.; Dolphin, D. J. Org. Chem. 1976, 41, 385.
12. (b) Nguyen, L. T. and Simth, K. M. Tetraherdorn Lett. 1996, 37, 7177.
13. 10. Half of 8 formed its μ-oxo dimer from the reaction with NaOH and the hydroxy complex was not so stable to isolate. Because of flipping over the neopentyl group, the hydroxy complex slowly changed to the μ-oxo dimer.