CS268891B1 - Halogenated derivatives of 5-acetoxy-7-oxo-7H-benzo (c) fluorene and a process for their preparation - Google Patents

Abstract

The solution concerns new halogen derivatives of 5-acetoxy-7-oxo-7H-oenzo(c)fluorene of the general formula I p2 1 2 in which -R denotes hydrogen and R chlorine or κ _i RZ bromine, serving as an intermediate stage in the preparation of antineoplastically active halogen derivatives of benzo(c)fluorene. Their preparation consists in the reaction of the corresponding halogen derivatives of 3-phenyl-1-oxo- -inden-2-yl acetic acid of the general formula II 1 2 with the above-mentioned meaning of R and R with acetic anhydride under boiling of the reaction mixture.

Description

The invention relates to new halogen derivatives of 5-acetoxy-7-oxo-7H-benzo(c)fluorene of the general formula I->

R^

212 in which R represents hydrogen and R represents chlorine or R and R represent bromine.

The compounds of general formula I with the above-mentioned meanings of R and R are valuable intermediates for the preparation of compounds with interesting biological effects, especially tetracyclic derivatives of benzo(c)fluorene. Benzo(c)fluorene derivatives exhibit significant antitumor, interferonogenic and antibacterial activity (Křepelka et al. Collect. Czech, Chem. Commun. 47, 1258 (1982), 47, 1857 (1982), Vančurová et al. Collect. Czech. Chem. Commun. 47, 1867 (1982). AO No. 212 669, USA patent No. 4,661.297, Šmejkal et al. Acta Virol. 29, 11 (1984) and compounds of general formula I are important precursors in their synthesis.

2

The compounds of general formula 1 with the above-mentioned meanings of R and R are prepared according to the invention from the corresponding halogen derivatives of 3-phenyl-1-oxo-inden-2-yl acetic acid of general formula II

R ²

(substances of general formula II are prepared according to Czechoslovak author's certificate No. 268890), in which R denotes hydrogen and R chlorine or R and R bromine, by reaction with acetic anhydride while boiling the reaction mixture.

More detailed information on the preparation of compounds of general formula I with the above-mentioned meanings of R1, R2 and R3 will be found in the following example, which does not limit the scope of the invention in any way.

Example

2,1l-Obromo-5-acetoxy-7-oxo-7H-benzo(c)fluorene

To 10 g (0.023 mol) of 3-(3-bromophenyl)-5-bromo-1-oxo-inden-2-yl acetic acid in a three-necked flask equipped with a reflux condenser and a stirrer was added 72 ml (0.76 mol) of acetic anhydride and the reaction mixture was stirred and heated to reflux (reaction temperature 133 °C) for 4 hours. The brown reaction mixture was then rapidly quenched with water while stirring to give a yellow solid with a melting point of 182-185 °C. 6.67 g (63.1%) of product was obtained.

2-Chloro-5-acetoxy-7-oxo-7H-benzo(c)fluorene was prepared analogously, melting point 226-230 °C.

Claims (4)

SUBJECT OF THE INVENTION 1. Halogen derivatives of 5-acetoxy-7-oxo-7H-benzo(c)fluorene of the general formula IH ² 1 2 12 in which R represents hydrogen and R represents chlorine or R and R represent bromine. 2. 2,1-Dibromo-5-acetoxy-7-oxo-7H-benzo(c)fluorene. 3. 2-Chloro-5-acetoxy-7~oxo-7H-benzo(c)fluorene. 4. A method for preparing substances according to point 1, of general formula I, characterized in that the corresponding halogenated 3-phenyl-1-oxo-inden-2-yl acetic acid of general formula II 1 2 12 in which R denotes hydrogen and R chlorine or R ^A and R bromine, are converted by reaction with acetic anhydride under boiling of the reaction mixture into compounds of general formula I with the above-mentioned meanings of R and R .