GB1023383A - - Google Patents

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Publication number
GB1023383A
GB1023383A GB1023383DA GB1023383A GB 1023383 A GB1023383 A GB 1023383A GB 1023383D A GB1023383D A GB 1023383DA GB 1023383 A GB1023383 A GB 1023383A
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United Kingdom
Prior art keywords
aminoalkyne
formula
alkyl
basic substance
hydroxamyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
Publication of GB1023383A publication Critical patent/GB1023383A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,023,383. Preparation of isoxazole derivatives. SHIONOGI & CO. Ltd. Nov. 5, 1963 [Jan. 24, 1963], No. 43698/63. Heading C2C. Isoxazole derivatives of the general formula wherein R is an isocyclic or heterocyclic ring, optionally substituted by an alkyl, alkoxy, hydroxy, halogeno, nitro or amino group, each of R<SP>1</SP> and R<SP>11</SP> is a hydrogen atom or an alkyl or alkenyl group or R<SP>1</SP> and R<SP>11</SP> may represent the residue of a 5- or 6-membered heterocyclic ring and A is an alkylene group, are prepared by the reaction of an aminoalkyne of the formula with a nitrile oxide of the formula in the presence of an inert solvent. The reaction may be effected at temperatures ranging from room temperature to reflux temperature and suitable solvents are alkanols, halogenoalkanes, aromatic hydrocarbons and ethers. Suitable values for R<SP>1</SP> and R<SP>11</SP> are C 1-5 alkyl groups, allyl, butenyl and pentenyl groups and, as a heterocyclic ring, pyrrolidino, piperidino, piperazino, N-alkyl-piperazino, morpholino and thiomorpholino rings. R may be, e.g., a furyl, thienyl, pyrazolyl, phenyl, cyclohexyl, pyridyl, pyrimidyl, naphthyl or quinolyl ring. A may be a straight or branched chain alkylene group. The nitrile oxide of the' Formula III, which is prepared by dehydrohalogenation in the presence of a basic substance of the hydroxamyl halide of the formula where X<SP>1</SP> is halogen, is unstable and the process of the invention may be carried out by adding a basic substance to a mixture of the aminoalkyne (II) and the hydroxamyl halide or by adding the aminoalkyne to a mixture of a basic substance and the hydroxamyl halide; the basic substance may be omitted and the aminoalkyne per se used as the dehydrohalogenation agent. The isoxazoles (I) may be converted into their acid addition or quaternary salts using the usual inorganic or organic acids or quaternizing agents. The process is illustrated by reference to a considerable number of examples.
GB1023383D Active GB1023383A (en)

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ID=1755073

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413289A2 (en) * 1989-08-18 1991-02-20 Sterling Winthrop Inc. Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
US6723724B2 (en) * 2000-12-04 2004-04-20 Korea Institute Of Science And Technology Isoxazolylalkylpiperazine derivatives having selective biological activity at dopamine D3 or D4 receptor, and preparation thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0413289A2 (en) * 1989-08-18 1991-02-20 Sterling Winthrop Inc. Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
EP0413289B1 (en) * 1989-08-18 1995-02-01 Sterling Winthrop Inc. Oxadiazolyl-phenoxyalkylisoxazoles and their use as antiviral agents
US6723724B2 (en) * 2000-12-04 2004-04-20 Korea Institute Of Science And Technology Isoxazolylalkylpiperazine derivatives having selective biological activity at dopamine D3 or D4 receptor, and preparation thereof

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