WO1998040363A1 - Procede de production de chinazol-4-ones - Google Patents

Procede de production de chinazol-4-ones Download PDF

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Publication number
WO1998040363A1
WO1998040363A1 PCT/EP1998/001254 EP9801254W WO9840363A1 WO 1998040363 A1 WO1998040363 A1 WO 1998040363A1 EP 9801254 W EP9801254 W EP 9801254W WO 9840363 A1 WO9840363 A1 WO 9840363A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
mol
acid
alkyl
quinazol
Prior art date
Application number
PCT/EP1998/001254
Other languages
German (de)
English (en)
Inventor
Gerhard Stucky
Beat Schmidt
Original Assignee
Lonza Ag
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lonza Ag filed Critical Lonza Ag
Priority to AU68275/98A priority Critical patent/AU6827598A/en
Publication of WO1998040363A1 publication Critical patent/WO1998040363A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms

Definitions

  • the invention relates to a process for the preparation of quinazol-4-one derivatives of the general formula
  • R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen, alkyl, alkenyl alkoxy, alkoxcarbonyl, aryl, arylalkyl, cyano or a halogen atom and R and R 6 are alkyl or alkenyl
  • R represents hydrogen, alkyl, alkenyl, alkoxy, alkoxycarbonyl, aryl, arylalkyl, cyano, a halogen atom or a radical of an ⁇ -amino acid and R represents hydrogen, alkyl, alkenyl, alkoxy, alkoxycarbonyl, aryl, arylalkyl, cyano or a halogen atom , implemented
  • alkyl group is understood to mean a straight-chain or branched, optionally substituted alkyl group having 1 to 6 C atoms, preferably 1 to 4 C atoms
  • Methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl should be mentioned by name
  • alkenyl group is understood to mean a straight-chain or branched optionally substituted alkenyl group having 2 to 6 C atoms, preferably 2 to 4 C atoms
  • An aryl group is advantageously an optionally substituted phenyl or naphthyl group
  • Suitable substituents for both the alkyl groups mentioned and for the aryl yeasts can be halogen, nitro, amino, alkylamino, dialkylamino, hydroxy, alkoxy, alkyl, and
  • Alkanoyl preferably with 1 to 6 carbon atoms
  • Halogen expediently means fluorine, chlorine, bromine or iodine
  • the derivatives of the anthranilic acid of the general formula II used as starting product are generally commercially available products, alternatively they can be prepared by known processes from the prior art
  • N-alkylimidocarbonic acid dialkyl esters of the general formula III can be easily and, for example, analogously to the specification of US Pat. No. 3,401,201 by reacting an iminocarbonic acid ester of the general formula
  • R has the meaning given with an ammonium salt of an alkylamine of the general formula
  • An acid residue is understood to mean the rest of a mineral acid such as chloride, sulfate or phosphate, or the rest of a carboxylic acid such as acetate
  • Suitable imidazole derivatives of the general formula IV are imidazole, alkylimidazoles such as, for example, 1-methylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, alkenylimidazoles such as, for example, 1-alkylimidazole, arylimidazoles such as, for example, 4-phenylimidazole, arylalkylimidazole -Benzylimidazole or imidazole with a residue of an ⁇ -amino acid such as histidine.
  • Imidazole is particularly preferably used
  • the imidazole derivative of the general formula IV is used in the reaction according to the invention in an amount of 5 mol% to 200 mol%, preferably from 80 mol% to 120 mol%, based on 1 mol of anthranile acid derivative of the general formula II
  • the reaction temperature is advantageously chosen between -10 ° C and 50 ° C, preferably between 0 ° C and 20 ° C
  • the reaction is generally complete after 2 h to 6 h, whereupon the quinazol-4-one derivative of the general formula I obtained can be removed in a professional manner, for example by aqueous work-up with extraction, from the reaction mixture
  • Preferred quinazol-4-one derivatives which can be prepared by the process according to the invention are derivatives of the general formula I in which R, R, R and R are identical or different and hydrogen, C] - alkyl, C 1-4 alkoxy or represent a halogen and R 5 and R 6 are the same or different and are for Cj. 4 - alkyl Examples:
  • Example 1 a) Preparation of the Iminokohlenkladipropylester from Cyanogen Chloride To propanol (919.9 g, 15 mol) was added sodium hydroxide (108.08 g, 2.675 mol)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Nouveau procédé de production de chinazol-4-ones de formule générale (I), dans laquelle un dérivé d'acide anthranilique est cyclisé avec N-alykimido-dialkyle carbonate en présence d'un dérivé d'imidazole. Les chinazol-4-ones sont des produits intermédiaires pour la production de substances actives fongicides.
PCT/EP1998/001254 1997-03-07 1998-03-05 Procede de production de chinazol-4-ones WO1998040363A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU68275/98A AU6827598A (en) 1997-03-07 1998-03-05 Method for producing quinazol-4-ones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH53997 1997-03-07
CH539/97 1997-03-07

Publications (1)

Publication Number Publication Date
WO1998040363A1 true WO1998040363A1 (fr) 1998-09-17

Family

ID=4189338

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/001254 WO1998040363A1 (fr) 1997-03-07 1998-03-05 Procede de production de chinazol-4-ones

Country Status (2)

Country Link
AU (1) AU6827598A (fr)
WO (1) WO1998040363A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166208A (en) * 1996-06-18 2000-12-26 E. I. Du Pont De Nemours And Company Preparation of fungicidal quinazolinones and useful intermediates

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026722A1 (fr) * 1993-05-12 1994-11-24 E.I. Du Pont De Nemours And Company Pyrimidinones bicycliques fusionnees a pouvoir fongicide
WO1997048684A1 (fr) * 1996-06-18 1997-12-24 E.I. Du Pont De Nemours And Company Preparation de quinazolinones fongicides et intermediaires utiles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026722A1 (fr) * 1993-05-12 1994-11-24 E.I. Du Pont De Nemours And Company Pyrimidinones bicycliques fusionnees a pouvoir fongicide
WO1997048684A1 (fr) * 1996-06-18 1997-12-24 E.I. Du Pont De Nemours And Company Preparation de quinazolinones fongicides et intermediaires utiles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166208A (en) * 1996-06-18 2000-12-26 E. I. Du Pont De Nemours And Company Preparation of fungicidal quinazolinones and useful intermediates

Also Published As

Publication number Publication date
AU6827598A (en) 1998-09-29

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