Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1996-03-20
1997-11-04
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568383, 549355, 549498, 549499, C07C 4976
Patent
active
056842066
DESCRIPTION:
BRIEF SUMMARY
This Application is the US National stage of PCT/FR94/00726 filed Jun. 16, 1994 which was published on Jan. 5, 1995 as WO95/00476.
The present invention relates to new .beta.-aminovinyl ketones having an aromatic substituent on the carbon attached to the amino group, to a process for the preparation of these compounds from nitriles and from a methyl organo ketone and to their use in the preparation of aromatic .beta.-diketones.
TECHNICAL CONTEXT OF THE INVENTION
Aromatic .beta.-diketones of general formula: ##STR2## in which the X symbol represents, for example, an aliphatic or cycloaliphatic group and Y represents, for example, an aromatic group, can advantageously be used as intermediates in the synthesis of 4-benzoylisoxazole derivatives of general formula: ##STR3## which can be broad-spectrum herbicides which are well known in the prior state of the art (cf. in particular EP-A-0,418,175).
The synthesis of a 4-benzoylisoxazole derivative from a diketone of formula (I) can be carried out by linking together the following two stages: dimethylformamide dialkyl acetal to lead to a product corresponding to the general formula: ##STR4## in which L is an O-alkyl group or an N,N-dialkylamino group; this reaction is generally carried out in an inert solvent such as, for example, diethyl ether or tetrahydrofuran, at a temperature ranging from 0.degree. C. to the reflux temperature of the mixture; and reaction is generally carried out in a solvent such as, for example, ethanol or acetonitrile, optionally in the presence of a base or of an acid acceptor such as, for example, triethylamine or sodium acetate.
As regards the starting .beta.-diketone of formula (I), its synthesis is commonly carried out by linking together the following three stages: alcohol such as, for example, methanol; and ##STR5## this reaction being carried out in the presence of a strong base under conditions in accordance with the Claisen condensation.
PURPOSE OF THE PRESENT INVENTION
The essential purpose of the present invention is that of proposing: .beta.-diketones which are capable of being used as intermediates in the synthesis of 4-benzoylisoxazole derivatives, excellent and the process is genuinely easy to develop on an industrial scale.
According to this access route, a .beta.-aminovinyl ketone which has an aromatic substituent on the carbon attached to the amino group is prepared which has the double characteristic of being a compound which, on the one hand, is novel and which, on the other hand, can be easily converted to the desired .beta.-diketone by subjecting, to the conversion reaction, either the aminovinyl ketone isolated from the reaction mixture in which it has been prepared or directly the said reaction mixture containing the aminovinyl ketone.
DESCRIPTION OF THE PRESENT INVENTION
I--In its first subject, the present invention relates to a .beta.-aminovinyl ketone of general formula: ##STR6## in which: R.sup.1 represents: carbon atoms which is optionally substituted with one or a number of halogen atom(s) and whose unsaturation is not conjugated with the ketone double bond; with one or a number of R.sup.4 or OR.sup.4 group(s) or one or a number of halogen atom(s); with one or a number of R.sup.4 or OR.sup.4 group(s) or one or a number of halogen atom(s), in which the ethylenic unsaturation is not conjugated with the ketone double bond; open-st.CR.sup.6 R.sup.7).sub.q --; carbon atoms; carbon atoms or a halogen atom (F, Cl, Br or I); a straight- or branched-chain alkyl group containing up to 4 carbon atoms; to 3; group formed by: atoms and in which the halo substitution is a monosubstitution which can range up to a virtually complete polysubstitution; a hydrogen atom or a straight- or branched-chain alkyl group containing up to 4 carbon atoms; carbon atoms, it being possible for the alkyl group to be optionally substituted with an OR.sup.4 group; integer ranging from 1 to 4; represents an integer ranging from 0 to 3; and q=0,
Mention may be made, as .beta.-aminovinyl ketones preferentially representative of the pres
REFERENCES:
Journal of Organic Chemistry;USSR;26#10;pp. 1801-1805; 1990.
Journal of Organic Chemistry;USSR;22#4;pp. 790-791;Sosnovskikh et al, 1986.
Journal of Organic Chemistry; 53#11;pp. 2426-2429, 1988.
Journal of the Chemical Society;Perkin Trans.l;#7; pp. 1401-1406;Nitta et al, 1985.
LA Chimica EL'Industria;vol. 56 #1;pp. 25-26;P.Barvo et al, 1974.
Sosnovskikh et al, Journal of Organic Chemistry of the USSR, vol. 26, No. 10, pp. 1801-1805, Oct. 1990.
Sosnovskikh et al, Journal of Organic Chemistry of the USSR, vol. 22, No. 4, pp. 790-791, Apr. 1986.
Guarna et al, Journal of Organic Chemistry, vol. 53, No. 11, pp. 2426-2429, May 1988.
Casado Michel
Le Roy Pierre
Pevere Virginie
Ivy C. Warren
Padmanabhan Sreeni
Rhone-Poulenc Argochimie
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