CA2021328A1 - Stereoselective preparation of z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes and novel intermediates - Google Patents

Stereoselective preparation of z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes and novel intermediates

Info

Publication number
CA2021328A1
CA2021328A1 CA002021328A CA2021328A CA2021328A1 CA 2021328 A1 CA2021328 A1 CA 2021328A1 CA 002021328 A CA002021328 A CA 002021328A CA 2021328 A CA2021328 A CA 2021328A CA 2021328 A1 CA2021328 A1 CA 2021328A1
Authority
CA
Canada
Prior art keywords
formula
compounds
azolylmethyloxiranes
conversion
preparation
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.)
Granted
Application number
CA002021328A
Other languages
French (fr)
Other versions
CA2021328C (en
Inventor
Reiner Kober
Rainer Seele
Heinz Isak
Eckhard Hickmann
Norbert Goetz
Thomas Zierke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
Individual
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
Priority claimed from DE3923674A external-priority patent/DE3923674A1/en
Priority claimed from DE3936823A external-priority patent/DE3936823A1/en
Application filed by Individual filed Critical Individual
Publication of CA2021328A1 publication Critical patent/CA2021328A1/en
Application granted granted Critical
Publication of CA2021328C publication Critical patent/CA2021328C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
    • C07C15/52—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed containing a group with formula
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Disclosed is a process for the stereoselective preparation of Z-1,2-diarylallyl chlorides of the general formula I
(See formula I) in which R1 and R2, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or an unsubstituted or substituted aromatic radical, and n and m are 1, 2 or 3. This process by which the compounds of formula I can be prepared in high isomeric purity, ie. with a high preference for the E- or trans-configuration of the phenyl radicals on the double bond, and in high yield, comprises dehydrating a chlorohydrin of the formula II
(See formula II) in which the radicals are as defined above, at up to 50°C in an inert ether or carboxylic acid ester as solvent and in the presence of a carboxylic anhydride and an organic or inorganic acid. The compounds of formula I that are so obtained are useful intermediates for the preparation of pharmacological, fungicidal and antimycotic active compounds.
CA002021328A 1989-07-18 1990-07-17 Stereoselective preparation of z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes and novel intermediates Expired - Lifetime CA2021328C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEP3923674.9 1989-07-18
DE3923674A DE3923674A1 (en) 1989-07-18 1989-07-18 New 1,2-di:aryl-3-chloro-propene cpds.
DEP3936823.8 1989-11-04
DE3936823A DE3936823A1 (en) 1989-11-04 1989-11-04 New 1,2-di:aryl-3-chloro-propene cpds.

Publications (2)

Publication Number Publication Date
CA2021328A1 true CA2021328A1 (en) 1991-01-19
CA2021328C CA2021328C (en) 2001-03-13

Family

ID=25883133

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002021328A Expired - Lifetime CA2021328C (en) 1989-07-18 1990-07-17 Stereoselective preparation of z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes and novel intermediates

Country Status (13)

Country Link
EP (1) EP0409049B1 (en)
JP (1) JP2975058B2 (en)
KR (1) KR0151380B1 (en)
AT (1) ATE86597T1 (en)
CA (1) CA2021328C (en)
DE (1) DE59001003D1 (en)
DK (1) DK0409049T3 (en)
ES (1) ES2054165T3 (en)
GR (1) GR3007315T3 (en)
HU (1) HU207701B (en)
MD (1) MD1255C2 (en)
RU (1) RU2096401C1 (en)
UA (1) UA37239C2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE284883T1 (en) * 2001-05-18 2005-01-15 Basf Ag METHOD FOR PURIFYING TRIAZOLYLMETHYL OXIRANES
WO2005056548A1 (en) * 2003-12-11 2005-06-23 Cheminova A/S Enantiomerically pure epoxiconazole and its use as crop protection agent
WO2011069912A1 (en) 2009-12-07 2011-06-16 Basf Se Triazole compounds, use thereof and agents containing said compounds
WO2011069894A1 (en) 2009-12-08 2011-06-16 Basf Se Triazole compounds, use thereof, and agents containing same
WO2011069916A1 (en) 2009-12-08 2011-06-16 Basf Se Triazole compounds, use thereof as a fungicide, and agents comprising same
BR112012023157B1 (en) 2010-03-16 2018-08-07 Basf Se Processes for Preparing a Compound, Compost, Using a Compound, and Using a Grignard Reagent
CN112661599B (en) * 2021-01-25 2022-10-04 浙江工业大学 Synthesis method of (Z) -3-halogenated-2- (4-fluorophenyl) -1- (2-chlorphenyl) propylene

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3422153A (en) * 1966-03-09 1969-01-14 Lilly Co Eli Novel aryl-substituted propenes and derivatives
US4013643A (en) * 1973-11-19 1977-03-22 G. D. Searle & Co. N,n-disubstituted 2,3-diphenylallylamines
DE2652313A1 (en) * 1976-11-17 1978-05-18 Basf Ag TRIAZOLE DERIVATIVES
DE3218129A1 (en) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen Azolylmethyloxiranes, their preparation and use as medicaments
DE3218130A1 (en) * 1982-05-14 1983-11-17 Basf Ag, 6700 Ludwigshafen AZOLYL METHYLOXIRANES, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM
NL8402755A (en) * 1983-09-22 1985-04-16 Sandoz Ag AZOLIC DERIVATIVES, METHOD FOR PREPARING THE SAME, PREPARATIONS CONTAINING THEM, AND USE THEREOF
CA1271764A (en) * 1985-03-29 1990-07-17 Stefan Karbach Azolylmethyloxiranes, their preparation and their use as crop protection agents

Also Published As

Publication number Publication date
HUT54335A (en) 1991-02-28
GR3007315T3 (en) 1993-07-30
ATE86597T1 (en) 1993-03-15
MD950079A (en) 1996-06-28
EP0409049A2 (en) 1991-01-23
EP0409049A3 (en) 1991-10-30
DK0409049T3 (en) 1993-04-13
JPH03163073A (en) 1991-07-15
HU904344D0 (en) 1990-12-28
UA37239C2 (en) 2001-05-15
MD1255B2 (en) 1999-06-30
HU207701B (en) 1993-05-28
MD1255C2 (en) 2000-03-31
RU2096401C1 (en) 1997-11-20
ES2054165T3 (en) 1994-08-01
DE59001003D1 (en) 1993-04-15
KR0151380B1 (en) 1998-10-15
KR910002747A (en) 1991-02-26
EP0409049B1 (en) 1993-03-10
CA2021328C (en) 2001-03-13
JP2975058B2 (en) 1999-11-10

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