Benzodifurantrione compounds and process

Details Benzodifurantrione compounds and process Benzodifurantrione compounds and process

1995-05-25

1997-04-29

Owens, Amelia

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D40700

Patent

active

056250800

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to benzodifurantriones and their tautomeric forms, to a process for their preparation, to intermediate acid chlorides, to processes for the preparation of benzodifuranones, to intermediate benzofuranones and to a process for the preparation of benzofuranones.
According to a first feature of the present invention there is provided a benzodifurantrione of Formula (1): ##STR3## wherein: W is unsubstituted or substituted aryl.
Examples of suitable substituent groups for W are alkyl; alkenyl; alkoxy; alkoxyalkyl; alkoxyalkoxy; alkylcarbonyl; alkoxycarbonyl; alkoxycarbonylalkoxy; alkoxyalkoxycarbonylalkoxy; alkylcarbonyloxyalkoxy; cyanoalkyl; cyanoalkoxy; hydroxyalkyl; hydroxyalkoxy; haloalkyl, especially fluoro-, chloro- or bromoalkyl; haloalkoxy, especially fluoro-, chloro- or bromoalkoxy; alkythio; arylthio; aryloxy; alkylsulphonyl; arylsulphonyl; halo, especially chloro or bromo; hydroxy; cyano; nitro; amino; alkylamino; dialkylamino; cycloalkylamino; alkylcarbonylamino; arylcarbonylamino; alkylsulphonylamino; arylsulphonylamino; cycloalkyl; and alkylamino and dialkylamino substituted by --CN, --Cl, --F, --Br, --OH, --COOC.sub.1-4 -alkyl, --COOC.sub.1-4 -alkylOC.sub.1-4 -alkyl, -phenyl, --OCOC.sub.1-4 -alkyl; and preferably such groups in which the alkyl or alkoxy contains from 1 to 8 carbon atoms, especially from 1 to 4 carbon atoms; the alkenyl contains from 2 to 6 carbon atoms, especially from 2 to 4 carbon atoms; the aryl is phenyl or naphthyl and the cycloalkyl contains from 3 to 8 carbon atoms, more preferably from 4 to 6 carbon atoms and especially 6 carbon atoms. Each alkyl, alkoxy or alkenyl may be straight or branched chain alkyl or alkoxy respectively.
W is preferably naphthyl or phenyl, more preferably a group of formula: ##STR4## wherein: Ring A is unsubstituted or is substituted by from 1 to 5 groups.
Preferred substituent groups for Ring A are selected from C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, hydroxy, C.sub.1-4 -alkoxy-C.sub.1-4 -alkoxycarbonylC.sub.1-4 -alkoxy, amino, C.sub.1-4 -alkylamino and (C.sub.1-4 -alkyl).sub.2 amino and combinations thereof.
Ring A is preferably unsubstituted or is substituted by from one to three groups. Where one substituent group is present in Ring A this is preferably in the 4-position, where two substituent groups are present in Ring A these are preferably in the 3- and 4-positions and where three substituent groups are present in Ring A these are preferably in the 3-, 4- and 5-positions.
The benzodifurantriones of Formula (1) may exist in a number of tautomeric forms, for example in forms represented by Formulae (1A) and (1B): ##STR5## and it is intended that the structure represented by Formula (1) includes all tautomeric forms.
According to a further feature of the present invention there is provided a process for the preparation of a benzodifurantrione of Formula (1) by reacting a compound of Formula (2): ##STR6## with a compound of Formula (3): ##STR7## wherein: W is as hereinbefore defined; and X and X.sup.1 each independently is halo; --Oalkyl; --OH; --NH.sub.2 ; --NHalkyl and --N(alkyl).sub.2.
The halo group represented by X and X.sup.1 is preferably --Cl, --Br or --I and more preferably --Cl or --Br. The --Oalkyl group represented by X and X.sup.1 is preferably --OC.sub.1-6 -alkyl, more preferably--OC.sub.1-4 -alkyl and especially --OCH.sub.3 or --OC.sub.2 H.sub.5. The --NHalkyl group represented by X and X.sup.1 is preferably --NHC.sub.1-6 -alkyl and more preferably --NHC.sub.1-4 -alkyl. The --N (alkyl).sub.2 group represented by X and X.sup.1 is preferably --N (C.sub.1-6 -alkyl).sub.2 and more preferably --N(C.sub.1-4 -alkyl).sub.2.
X and X.sup.1 are preferably --Cl or --Br.
The reaction of the compound of Formula (2) with the compound of Formula (3) may occur in one or in two stages depending on the reaction conditions used.
In a two stage reaction a compound of Formula (2) is firstly reacted with a compound of Formula (3) to form a compound of Formula (4): ##STR8## wherein: W and X are as hereinbefore defined.
The first

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