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United States Patent (19) 11 Patent Number: 4,772,719 Chiarino Et Al

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United States Patent (19) 11 Patent Number: 4,772,719 Chiarino Et Al United States Patent (19) 11 Patent Number: 4,772,719 Chiarino et al. 45 Date of Patent: Sep. 20, 1988 54 PROCESS FOR THE PREPARATION OF (56) References Cited 3,5-DISUBSTITUTED ISOXAZOLES PUBLICATIONS 75 Inventors: Dario Chiarino; Alberto Sala, both of Christoph Grundmann et al., J. Org. Chem., 30(8); pp. Monza; Mauro Napoletano, Milan, all 2809-2812 (1965). of Italy Chemical Abstracts, 56, 12869e (1962). Primary Examiner-Donald G. Daus Assistant Examiner-E. Bernhardt 73) Assignee: Zambon S.p.A., Vicenza, Italy Attorney, Agent, or Firm-Stevens, Davis, Miller & Mosher 21 Appl. No.: 900,147 57 ABSTRACT 22, PCT Filed: Dec. 10, 1985 A novel process for the preparation of 3-bromo- and 3-chloro-5-substituted isoxazoles is provided. Dibromo or dichloro-formaldoxime is reacted with an excess of 86 PCT No.: PCT/EP85/00693 an 1-alkyne derivative of the formula S371 Date: Jul. 24, 1986 S 102(e) Date: Jul. 24, 1986 where R is hydrogen, phenyl or 1-6 Calkyl optionally 87 PCT Pub. No.: WO86/03490 substituted by halogen, OH, OR", CHO, COR", COOR", PCT Pub. Date: Jun. 19, 1986 CONH2, CONR'R' or NHCOR' where, in turn, R' and R", which may be the same or different, are a 1-6 C (30) Foreign Application Priority Data alkyl or haloalkyl, in the presence of (i) at least an equi molecular amount, with respect to the dibromo- or Dec. 13, 1984 IT Italy ............................... 24023 A/84 dichloro-formaldoxime, of an alkaline base selected from the class consisting of sodium and potassium car 51) Int. Cl'............................................ CO7D 261/10 bonate and bicarbonate and (ii) an inert solvent in which 52 U.S.C. .................................... 548/247: 548/125; the 1-alkyne is soluble at room temperature. 548/248 58) Field of Search ........................ 548/247, 240, 248 3 Claims, No Drawings 4,772,719 1. 2 ylene, 4-chlorophenylacetylene, 4-methylphenylacety PROCESS FOR THE PREPARATION OF lene, 2,4-dimethylphenylacetylene, and the like; com 3,5-DISUBSTITUTED ISOXAZOLES pounds containing a hydroxy group such as 3-butyn-2- ol, 3-butyn-1-ol, propargyl alcohol, 1,1-dimethylpropar This invention relates to a process for the preparation 5 gyl alcohol, 1-pentyn-3-ol, 1-hexyn-3-ol, l-phenylpro of 3,5-disubstituted isoxazoles and more specifically of pargyl alcohol and the corresponding derivatives in 5-substituted 3-haloisoxazoles. which the hydroxy group is protected such as in the The process of this invention comprises the reaction form of tetrahydropyranyl or acyl derivatives; com of a dihaloformaldoxime with an excess of an 1-alkyne pounds containing an optionally protected carbonyl derivative in the presence of an alkaline base in an inert 10 group like acetal or thioacetal, such as for example solvent. propargyl aldehyde, methyl ethynyl ketone, methyl The cycloaddition of a dihaloformaldoxime with an propargyl ketone, ethyl ethynyl ketone, propyl ethynyl alkyne has precedents in the literature (Gazz. Chim. ketone, phenyl ethynyl ketone; esters like ethyl propio Ital. 91, 47 (1967) and 99, 1107 (1969)). In accordance late or amides of propiolic and 3-butynoic acid; com with this procedure the alkyne is used as organomag- 15 pounds containing a protected amino group such as for nesium derivative. example amides of propargylamine, alpha-methyl This fact does limit its applicability only to the al propargylamine, alpha,alpha-dimethylpropargylamine, kynes which do not contain functional groups reactive alpha,alpha-diethylpropargylamine, and N-tert.butyl to Grignard compounds. propargylamine; halogenated compounds such as for This procedure cannot be used on industrial scale 20 example propargyl chloride, propargyl bromide, 4 because of the well-known difficulties in processing and chlorobutyne-l; compounds containing different func handling the Grignard compounds. tional groups such as for example 2-hydroxy-3-butynoic 3,5-Disubstituted-isoxazoles, but not 3-halo, 3 acid esters. hydroxy or 3-alkoxy-5-substituted isoxazoles, may be With the process of this invention are prepared 3 prepared by cycloaddition according to C. Grundmann, 25 chloro or 3-bromoisoxazoles having at 5-position a P. Griinanger "The nitrile-oxides' Springer-Verlag, large number of substituents such as alkyl, aryl, hydrox Berlin (1971). alkyl, alkylcarbonyl, alkylcarbonylalkyl, formyl, alk Cycloadditions of dihaloformaldoximes with alkenes oxycarbonyl, alkoxycarbonylalkyl, aminoalkyl, mono to obtain the corresponding 5-substituted 3-halo-isox or dialkylaminoalkyl, haloalkyl, and the like, wherein azolines are known (Tetrahedron Letters, 21, 229, 30 each alkyl or alkoxy group has from 1 to 6 carbon (1980); 23,4563, (1982) and 25, 478 (1984)). However, atons. this reaction was specifically studied for the preparation In accordance with the preferred embodiment of this of alpha-amino-3-chloro-4,5-dihydro-5-isoxazolylacetic invention dibromo- or dichloroformaldoxime is reacted acid and its 3-bromo analog, these compounds being with an 1-alkyne derivative of formula R-C=CH antitumor agents known as Acivicin and Bromo-acivi- 35 wherein R is hydrogen, phenyl or 1-6C alkyl optionally cin, respectively. subtituted by halogen, OH, OR", CHO, COR, COOR, This cycloaddition is carried out by reaction of an CONH2, CONR'R'', NHCOR' where in turn R and excess of dihaloformaldoxime (3-5 times) with the al R", the same or different, are an 1-6C alkyl or haloal kene in the presence of a base or of silver nitrate. kyl, to afford 3-bromo- or 3-chloro-5-substituted isox Disappointing results were obtained when the proce azoles. dure was used to condensate a dihaloformaldoxime with When desired, it is possible to transform these substit an 1-alkyne derivative. The main reaction product was uents by conventional procedures. Thus, for example, it a dihalofuroxan resulting from the reaction between is possible to substitute the 3-bromo or 3-chloro atom two molecules of dihaloformaldoxime. with an alkoxy or arylalkoxy group by reaction with The presence of relevant amounts of furoxan is a 45 aqeous KOH and the corresponding alcohol. Said serious drawback and must be avoided as much as possi group may then be converted into hydroxy and this ble because of its dangerousness (J. Chem. Soc. Perkin may be alkylated with alkylanting agents containing Trans. I; 294 (1983)) and of problems connected with different functional groups; examples of such alkylating the isolation of the desired isoxazole derivative. agents are the chlorohydrins, bromohydrins, epichloro We have now surprisingly found that 3-halo-isox 50 hydrins, and aminoalkyl halides. azoles having a wide range of substituents at 5-position Similarly the hydroxy of a hydroxyalkyl group at can be easily prepared with high selectivity and with 5-position may be converted into the corresponding high yields by reacting a dihaloformaldoxime with an acyloxy, tosyloxy, mesyloxy or haloderivative and excess (from 2 to 5 times) of an 1-alkyne derivative in these may be substituted with nucleophilic groups such the presence of an alkaline base in an inert solvent at 55 as amines, alcohols, and the like. room temperature. The formation of furoxans is mini The same hydroxyalkyl group may be oxidated to mized (see Example 6). carbonyl or carboxyl group. The dihaloformaldoximes which are useful in the The carbonyl of an alkylcarbonyl, alkylcarbonylalkyl process of the present invention are dichloroformaldox or formyl group may be reduced to alcohol or con ime and dibromoformaldoxime. 60 verted into a carbonyl derivative such as hydrazone or The high versatility of the process of this invention is oxine. due to the fact that a variety of 1-alkyne derivatives can Hydrolysis of isoxazoles bearing an alkoxycarbonyl be successfully used to afford 3-chloro or 3-bromoisox alkyl group at 5-position affords the corresponding azoles having at 5-position various different groups. carboxylic acids from which various derivative such as Suitable 1-alkyne derivative comprise hydrocarbons 65 acyl halides, amides and salts or other esters may be such as propyne, 1-butyne, 1-pentyne, 1-hexyne, 3 prepared by conventional procedures. methyl-1-butyne and acetylene; aryl-derivatives option The 3,5-disubstituted isoxazoles which can be pre ally substituted at the aromatic ring such as phenylacet pared by the process of this invention may be used in 4,772,719 3. 4. various fields and may also be useful as intermediates The 5-isoxazolylacetic derivatives are intermediates for the preparation of other compounds. for the preparation of compounds having antibiotic Thus for example, 3-chloro- and 3-bromoisoxazoles activity (U.K. patent application No. 2,018,247 (C.A., having at 5-position an optionally substituted phenyl 93, 26449y), German patent application No. 2,409,949 group are endowed with anthelmintic activity (J. Med. 5 (C.A., 82, 31341j), U.K. Pat. No. 1,464,377). Chem., 20, 934, (1977)) or nematocidal activity (U.S. Preparation of the above cited compounds and inter Pat. No. 3,879,532). They can be readily prepared ac mediates and of other 3,5-disubstituted isoxazoles may cording to the process of this invention by reaction of therefore be performed in accordance with the process dichloro- or dibromoformaldioxime with phenylacety of the present invention by reacting dichloro- or di lene optionally substituted at the phenyl ring. O bromoformaldioxime with an excess (from 2 to 5 mol) of Replacement of the bromine or the chlorine atom at an 1-alkyne derivative and optionally performing the 3-position with a hydroxy group gives 3-hydroxy-5- appropriate transformation of the substituents at 3- or phenylisoxazoles also having anthelmintic activity (J. 5-position. Med. Chem. 20, 934, (1977)) or antimicrobic activity The reaction is carried out in an inert solvent in the (Japanese patent application No. 57/165305 (C.A., 99, 15 presence of a mild alkaline base at room temperature. 34520d)). Said compounds are useful also as intermedi Suitable solvents are the solvents in which the 1 ates for preparing herbicides (Japanese patent applica alkyne derivative is soluble at room temperature.
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