Organic compounds -- part of the class 532-570 series – Organic compounds – Rare earth containing
Patent
1989-12-21
1992-10-27
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Rare earth containing
540465, 540467, 540470, C07D48722, C07D25900
Patent
active
051590654
ABSTRACT:
The present invention involves, in addition to many unique substituted sapphyrins, a novel method for synthesizing sapphyrins with good efficiency and high yield. An improved 9-step synthesis of substituted sapphyrins, e.g., the two C.sub.2 symmetric sapphyrins, compounds 2 and 4 of FIG. 1C, is described herein. This synthesis involves as an important step the condensation between a tripyrrane diacid and a diformyl bipyrrole. The key tripyrrane component is prepared in three high-yield steps from readily available pyrrolic precursors and the bipyrrole portion is prepared in four steps from ethyl 3-methyl-4-methylpyrrole-2-carboxylate in roughly 33% yield overall.
REFERENCES:
patent: 4883790 (1989-11-01), Levy et al.
patent: 4915683 (1990-05-01), Sieber
patent: 4935498 (1990-06-01), Sessler et al.
Harriman et al., J. Chem. Soc., Chem. Commun., (1989) 314-316.
Sessler et al., Chem. Absts., vol. 111:125716e (Oct. 2, 1989).
Sessler et al., J Amer Chem Soc, 110(6):5586-5588 (1988).
Sessler et al., "Synthetic and structural studies of sapphyrin, a 22-pi-electron pentapyrrolic `Expanded Porphyrin`," Journal of the American Chemical Society, 112:2810-2813 (1990).
Maiya et al., "In vitro photodynamic activity of diprotonated sapphyrin: a 22-pi-electron pentapyrrolic porphyrin-like macrocycle," Chemical Abstracts, 112:348-349, Abstract #194584t (1990).
Edward A. Cuellar et al., Synthesis and Characterization of Metallo and Metal-Free Octaalkylphthalocyanines and Uranyl Decaalkylsuperphthalocyanines.sup.1. Inorg. Chem. 1981, 20, 3766-3770.
Victor J. Bauer et al., Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles. J. Am. Chem. Soc. 1983, 105, 6429-6436.
Hans Rexhausen et al., The Synthesis of a New 22 .pi.-Electron Macrocycle: Pentaphyrin. Chem. Soc., Chem. Commun., 1983.
M. J. Broadhurst et al., 18- and 22-.pi.-Electron Macrocycles Containing Furan, Pyrrole, and Thiophen Rings. Chemical Communications, 1969 pp. 1480-1482.
M. J. Broadhurst et al., The Synthesis of 22 .pi.-Electron Macrocycles. Sapphyrins and Related Compounds. J. Chem. Soc. Perkin I, 1972, 2111.
Tobin J. Marks et al., Large Metal Ion-Centered Template Reactions. Chemical and Spectral Studies of the "Superphthalocyanine" Dioxocyclipentakis (1-iminoisoindolinato) uranium(VI) and Its Derivatives. American Chemical Society 1978.
Cyr Michael J.
Sessler Jonathan L.
Board of Regents , The University of Texas System
Shah Mukund J.
Ward E. C.
LandOfFree
Sapphyrins, derivatives and syntheses does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Sapphyrins, derivatives and syntheses, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Sapphyrins, derivatives and syntheses will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-906446