Method of producing paraquinones

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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546 78, 546101, 546108, 548421, 548427, 549 24, 549 26, 549388, 549389, 260351, 2603515, 260365, 260369, 260383, 260396, C07C 5016, C07C 5022, C07D22118, C07D33504

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047390620

ABSTRACT:
A new widely-applicable method has been found for synthesis of 9,10-anthraquinones and similar chemical compounds of wide use in industry and pharmacology, by reacting suitable aromatic substrates with activated dicarboxylic acids (more particularly dichlorides) in the presence of metal halides. The special characteristics of the reaction are the good yields, high selectivity, the possibility of operating in a single reactor and the use of starting compounds which are cheap and easily available on the market.

REFERENCES:
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patent: 4312811 (1982-01-01), Schoemans et al.
patent: 4393221 (1983-07-01), Broadhurst et al.
Kerdesky et al, Journal of Amer. Chem. Soc., vol. 110, No. 11, p. 3635, 1978, "A General, Selective & Facile Method for Ketone Synthesis from Acid Chlorides & Organotin Comp. Catalyzed by Pd".
Karsten Krohn, "Total Synthesis of Anthracyclinone" Angew. Chem. Int. Ed. Engl. 25 (1986) 790-807.
Russell, et al. "A Caveat Regarding Chiroptical Measurements of Chiral Anthracyclinones" Tetrahedron Letters, 25 No. 50 p. 5817 (1984).
Kimball, et al. "Anthracyclines and Related Substances, 4, A Novel Regio- and Stereoselective Total Synthesis of 7-Epidaunomycinone and Daunomycinone" Tetrahedron Letters, vol. 23, No. 38, pp. 3871-3874 (1982).
Kim, et al. "Anthracyclines and Related Substances I, A New Freidel-Crafts Alkylation Reaction Using 3-Bromophthalides, Efficient Synthesis of Islandicin, " Tetrahedron Letters No. 4, pp. 331-334, (1979).

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