Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-08-08
1997-09-02
Owens, Amelia
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
560 60, C07D31176, C07C 6976
Patent
active
056633700
DESCRIPTION:
BRIEF SUMMARY
The present invention provides chemical compounds which are useful as intermediates for the preparation of agrochemicals (especially fungicides), to processes for preparing said chemical compounds and to methods of using them to prepare other intermediates.
The compounds of the invention can be used to prepare fungicidal acrylic ester derivatives, for example those known from EP-178826, EP-370629, EP-414153, EP-460575, WOg3/16986, WO92/18494, WO90/07493, EP-586393 or WO94/08968.
The present invention provides a compound of formula (I), wherein R is hydrogen or methyl; or a compound of formula (Ia) wherein M is an alkali metal or alkaline earth metal cation and n is 1 or 2.
It is preferred that M is an alkali metal (especially sodium or potassium).
In one aspect present invention provides a process for the preparation of a compound of formula (I), wherein R is methyl, the process comprising reacting isochromanone with trimethyl orthoformate in the presence of an acid anhydride.
In another aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is hydrogen, the process comprising reacting a compound obtainable by treating isochromanone with a source of methoxide anions, with an alkyl formate and acidifying the product so formed.
In a further aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is hydrogen, the process comprising the steps: the product so formed.
In a still further aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is methyl, the process comprising reacting a compound obtainable by treating a compound of formula (I), wherein R is hydrogen, with a suitable base, with a suitable methylating agent.
In another aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is methyl, the process comprising the steps: suitable base; and,
In yet another aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is methyl, the process comprising the steps: of methoxide anions, with an alkyl formate and acidifying the product so formed;
In a further aspect the present invention provides a process for the preparation of a compound of formula (I), wherein R is methyl, the process comprising the steps: the product so formed;
In a still further aspect the present invention provides a process for the preparation of a compound of formula (II), wherein X is chlorine or bromine, the process comprising reacting a compound of formula (I), wherein R is methyl, with a thionyl halide of formula SOX.sub.2 (wherein X is as previously defined) and reacting the product so formed with methanol.
In another aspect the present invention provides a process for the preparation of a compound of formula (II), wherein X is chlorine or bromine, the process comprising the steps: formula (I) (wherein R is hydrogen) with a suitable base, with a suitable methylating agent; and, SOX.sub.2 (wherein X is as previously defined) and reacting the product so formed with methanol.
In yet another aspect the present invention provides a process for the preparation of a compound of formula (II), wherein X is chlorine or bromine, the process comprising the steps: suitable base; and, SOX.sub.2 (wherein X is as previously defined) and reacting the product so formed with methanol.
In a further aspect the present invention provides a process for the preparation of a compound of formula (II), wherein X is chlorine or bromine, the process comprising the steps: of methoxide anions, with an alkyl formate and acidifying the product so formed; SOX.sub.2 (wherein X is as previously defined) and reacting the product so formed with methanol.
In a still further aspect the present invention provides a process for the preparation of a compound of formula (II), wherein X is chlorine or bromine, the process comprising the steps:
(a) reacting isochromamone with a source of methoxide anions; the product so for
REFERENCES:
Barbier, M., "Synthesis of Substituted 2-Phenyl .alpha..beta.-Unsaturated Aliphatic Acids", Synthetic Communications, vol. 19 (9&10), pp. 1661-1667 (1989).
Black, Gerald G., "The Synthesis and Flash Vacuum Pyrolysis of 4-Alkenylisochroman-3-Ones", Journal of Chemical Research, Synopses., vol. 9, Sep. 1986,. pp. 332-333.
Kosuge, Takuo et al., "Synthesis and Some Reactions of 6-Bromooxindole", Chem. Pharm. Bull., vol. 33 (1985), pp. 1414-1418.
Elix, J. A. et al., "Annelated Furans, XIII. Methylation of 3-Acylbenzofuran-2(3H)-Ones", Aus. J. Chem., vol. 26 (1973), pp. 1079-1091.
Hutchings, Michael G., "The Regio-and Stereochemistry of the Alkoxide-Induced Ring-Opening of Methoxymethylidene-Substituted Homophthalic Anhydride", Tetrahedron, vol. 44 (1988), No. 12, pp. 3727-3734.
Wolfbeis, Otto S., "Uber die Umalgerung von Alkoxymethylen-und Amino-methylenhomophthalsaureanhydriden zu Isocumarinen bzw. Isochinolinonen", Liebigs Ann. Chem., (1981), pp. 819-827.
Bowden Martin Charles
Brown Stephen Martin
Owens Amelia
Snyder Joseph R.
Thomson Marian T.
Zeneca Limited
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