Preparation of anthraquinones

Details Preparation of anthraquinones Preparation of anthraquinones

1993-11-09

1995-02-07

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Polycyclo ring system containing anthracene configured ring...

552239, 552240, 552241, 552243, 552245, 552246, 552247, 552248, 552251, 552252, 552253, 552254, 552255, 552256, 552260, C07C22100

Patent

active

053877047

ABSTRACT:
Process for preparing amino- and carbamoyl-substituted anthraquinones by Diels-Alder reaction of an N-butadienylcarbamic acid ester of the formula H.sub.2 C.dbd.CH--CH.dbd.CH--NH--COOR.sup.2, wherein R.sup.2 is alkyl or phenylalkyl, with a 1,4-naphthoquinone or with 1,4-benzoquinone to form a carbamoyl-substituted hydroanthraquinone intermediate and by oxidation of this intermediate with an oxygen-containing gas in a tertiary amine and in the presence of a copper salt to obtain a carbamoyl-substituted anthraquinone product. The Diels-Alder reaction and the oxidation reaction can be carried out as a one-pot synthesis or in separate steps. The carbamic acid ester reactant provides a blocking group represented by --COOR.sup.2, and this blocking group is optionally removed by treatment of the carbamoyl-substituted anthraquinone with an alkaline hydroxide solution.

REFERENCES:
patent: 3998857 (1976-12-01), Oediger
Tetrahedron Letters, vol. 28 (1987) pp. 4529-4532.
Houben-Weyl, Methoden der organischen Chemie, vol. 7/3c, pp. 23-31.

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