Quinonoid intermediates from chloroprene

Details Quinonoid intermediates from chloroprene Quinonoid intermediates from chloroprene

1978-10-10

1979-08-14

Curtis, Allen B.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260383, 260384, C07C 4972, C07C 4974, C07C 4980, C09B 382

Patent

active

041645030

ABSTRACT:
There is provided a novel and efficent method of synthesizing 7,10-dihydro-6,11-dihydroxy-5,9,12(8H)-naphthacenetrione and analogs thereof substituted in the 1,2,3 or 4 positions. The novel method comprises reacting the appropriate quinizarinquinone with a haloprene under Diels-Alder conditions, followed by aromatization and treatment with strong acid under very mild temperature conditions. The products of this process are important intermediates in the synthesis of daunomycin and its analogs which are useful in the therapy of neoplastic ailments.

REFERENCES:
patent: 3803124 (1974-04-01), Arcamone et al.
patent: 4021457 (1977-05-01), Kende et al.
patent: 4070382 (1978-01-01), Kende et al.
Chemical Abstract, vol. 82, #169826c, "Polycyclic Quinone Charge Transfer Complexes", Medne et al., 1975.
Chemical Abstract, vol. 63, #16273b, "Rhodomycins IX Antibiotics from Actinomycetes", Brockmann et al., 1965.

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