Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1995-03-16
1996-02-27
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544165, 544176, 564171, C07D295192, C07C23112
Patent
active
054950198
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/01803 filed Jul. 8, 1993.
The invention concerns a new process for the preparation of 3,3-diaryl acrylic acid amides of the general formula I ##STR3## in which A represents ##STR4## B represents ##STR5## and Q represents ##STR6## where
R.sub.1 represents a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, amino, mono- or di-(C.sub.1-4 alkyl)amino, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-4 alkenyloxy, C.sub.3-4 alkynyloxy or C.sub.3-6 cycloalkyl group;
R.sub.2 represents a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group or a halogen atom;
R.sub.3 represents a hydrogen or halogen atom;
R.sub.4 represents a hydrogen or halogen atom or a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group;
R.sub.5 represents a hydrogen atom, a phenyl group optionally substituted by one or more substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen, phenyl and phenoxy moieties, a C.sub.1-12 alkyl group optionally substituted by one or more halogen atoms, a C.sub.3-7 cycloalkyl group, a C.sub.2-6 alkenyl or a C.sub.2-6 alkynyl group each optionally substituted by a phenyl group, or a naphthyl or C.sub.5-8 cycloalkenyl group;
--X--Y-- represents a single bond or a --O--, --S(O).sub.p --, --N.dbd.N--, --CHR.sub.10 --O--, --O--CHR.sub.10 --, --CHR.sub.10 --S(O).sub.p --, --S(O).sub.p --CHR.sub.10 --, --C.sub.n H.sub.2n --, --HC.dbd.CH-- or --C.ident.C-- moiety, in which moieties p represents 0, 1 or 2 and n represents an integer from 1 to 10;
R.sub.6 represents a C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl, benzyl, C.sub.3-4 alkenyl or C.sub.3-4 alkynyl group;
R.sub.7 represents a C.sub.1-4 alkyl group;
R.sub.8 represents a hydrogen atom or a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group; and
R.sub.9 and R.sub.10 independently represent a hydrogen atom or a C.sub.1-4 alkyl group.
Compounds of formula I are fungicidally active and are particularly useful in the control of phytopathogenic fungi, especially Plasmopara viticola and Phytophthora infestans. Particularly preferred compounds of formula I in this respect are those in which A represents a 3,4-dimethoxyphenyl, 3-ethoxy-4-methoxyphenyl, 3-chloro-4-methoxyphenyl, 3-bromo-4-methoxyphenyl, 3-methyl-4-methoxyphenyl, 3-ethyl-4-methoxyphenyl, 3-propyl-4-methoxyphenyl, 3,4-dimethylphenyl, 3-amino-4-methoxyphenyl, 3,5-dichloro-4-aminophenyl or 3-methoxy-4-methylphenyl group and, of these, 3,4-dimethoxyphenyl is especially preferred, and B represents 4-chlorophenyl or 4-(4-chlorophenoxy)phenyl. It is also preferred that Q represents a morpholino group. Especially preferred compounds of the general formula I are 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl) acrylic acid morpholide and 3-[4-(4-chlorophenoxy)phenyl]-3-(3,4-dimethoxyphenyl) acrylic acid morpholide.
Compounds of the general formula I as well as processes for their preparation have been described in European patent applications EP 120 321 and EP 219 756.
A more efficient process for the preparation of compounds of the general formula I has been described in European patent application EP 294 907. In this document the condensation of a substituted benzophenone and an appropriate acetamide has been described in the presence of a strong base such as potassium tert-butylate, an alkali metal hydroxide or carbonate, or tert-butyl lithium. However, these methods give yields of less than 50%, due to decomposition of the starting materials and/or the end product under the influence of the base. Further, sometimes an intermediate is formed which has to be converted in a second step.
European patent application EP 329256 reveals that the yield of the above condensation reaction is considerably improved if a sodium tertiary alcoholate is used as the base. Such alcoholates react readily with the water which is produced in the course of the reaction yielding the corresponding alcohol and sodium hydroxide. This hydroxide, together with the alcoholate, in turn cleaves base-sensitive reactants, especially the acetamide, or the desired product, often to a large extent and thus reduces the yield from the process. Attempts to ove
REFERENCES:
Chodkiewicz, "Preparation d'amides et de nitriles beta-alcools diaryles; deshydratation en derives alpha-ethyleniques correspondants", Bulletin De La Societe Chimique De France, pp. 1586-1591, Paris, France 1958.
Curtze Jurgen
Haertel Bodo
American Cyanamid Company
Hill Gregory M.
Ramsuer Robert W.
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