DD237836A5 - Verfahren zur synthese der diastereomeren formen von triazolyl-o,n-acetalen - Google Patents

Verfahren zur synthese der diastereomeren formen von triazolyl-o,n-acetalen Download PDF

Info

Publication number: DD237836A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; optionally substituted; triazole; halogen; carbon atoms
Prior art date: 1984-07-20

Application number

DD85278737A

Other languages

German (de)

English (en)

Inventor

Johann Gasteiger

Karlheinz Kaufmann

Rudolf Mengel

Original Assignee

��@��k��

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.)

1984-07-20

Filing date

1985-07-18

Publication date

1986-07-30

1985-07-18 Application filed by ��@��k�� filed Critical ��@��k��

1986-07-30 Publication of DD237836A5 publication Critical patent/DD237836A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 39
230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
238000003786 synthesis reaction Methods 0.000 title claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 title claims description 8
150000002924 oxiranes Chemical class 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
-1 4-chlorophenoxy Chemical group 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 13
150000002989 phenols Chemical class 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
239000003085 diluting agent Substances 0.000 claims description 12
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Chemical group 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 9
GFFLDESXTQQGEI-UHFFFAOYSA-N 2-bromo-3-tert-butyloxirane Chemical compound CC(C)(C)C1OC1Br GFFLDESXTQQGEI-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
159000000000 sodium salts Chemical class 0.000 claims description 6
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 4
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims 4
150000001875 compounds Chemical class 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000002585 base Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
150000003852 triazoles Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 5
239000012038 nucleophile Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
150000004707 phenolate Chemical class 0.000 description 4
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZAMHHRMCMPEUKX-RNFRBKRXSA-N 1-[(2r,3s)-3-tert-butyloxiran-2-yl]-1,2,4-triazole Chemical compound CC(C)(C)[C@@H]1O[C@H]1N1N=CN=C1 ZAMHHRMCMPEUKX-RNFRBKRXSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
RGEZZTFVDYNHMD-GHMZBOCLSA-N (2S,3S)-2-tert-butyl-3-(4-chlorophenoxy)oxirane Chemical compound C(C)(C)(C)[C@@H]1O[C@H]1OC1=CC=C(C=C1)Cl RGEZZTFVDYNHMD-GHMZBOCLSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 2
IYILYLSXJIVJMR-UHFFFAOYSA-N 2-tert-butyl-3-chlorooxirane Chemical compound CC(C)(C)C1OC1Cl IYILYLSXJIVJMR-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
OWXCNOQKAWVBSU-UHFFFAOYSA-N 1,2,4-triazolylsodium Chemical compound [Na+].C1=N[C-]=NN1 OWXCNOQKAWVBSU-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 description 1
IIQAWMPOSKYFSS-UHFFFAOYSA-N 3,3-dimethyl-2-(1,2,4-triazol-1-yl)butanal Chemical compound CC(C)(C)C(C=O)N1C=NC=N1 IIQAWMPOSKYFSS-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000005846 Triadimenol Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000006065 biodegradation reaction Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000002464 fungitoxic effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000004321 preservation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
NVMNEWNGLGACBB-UHFFFAOYSA-N sodium;1,2-diaza-4-azanidacyclopenta-2,5-diene Chemical compound [Na+].C=1N=C[N-]N=1 NVMNEWNGLGACBB-UHFFFAOYSA-N 0.000 description 1
CFPLEOLETMZLIB-UHFFFAOYSA-M sodium;4-chlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C=C1 CFPLEOLETMZLIB-UHFFFAOYSA-M 0.000 description 1
BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/36—Halogenated alcohols the halogen not being fluorine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- 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
- 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
- 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
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD85278737A 1984-07-20 1985-07-18 Verfahren zur synthese der diastereomeren formen von triazolyl-o,n-acetalen DD237836A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843426906 DE3426906A1 (de)	1984-07-20	1984-07-20	Verfahren und zwischenprodukte zur synthese diastereomerer verbindungen

Publications (1)

Publication Number	Publication Date
DD237836A5 true DD237836A5 (de)	1986-07-30

Family

ID=6241207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85278737A DD237836A5 (de)	1984-07-20	1985-07-18	Verfahren zur synthese der diastereomeren formen von triazolyl-o,n-acetalen

Country Status (14)

Country	Link
US (1)	US4751312A (da)
EP (1)	EP0169439B1 (da)
JP (1)	JPS6176466A (da)
KR (1)	KR860001079A (da)
CN (1)	CN85105611A (da)
AT (1)	ATE45569T1 (da)
BR (1)	BR8503453A (da)
CA (1)	CA1250585A (da)
DD (1)	DD237836A5 (da)
DE (2)	DE3426906A1 (da)
DK (1)	DK330885A (da)
HU (1)	HUT39167A (da)
IL (1)	IL75832A (da)
ZA (1)	ZA855466B (da)

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KR101101919B1 (ko) *	2011-04-07	2012-01-02	이상민	회전 감속기를 이용한 무선 소형 전동 드라이버
WO2014075676A1 (en) *	2012-11-15	2014-05-22	V-Biotek Holding Aps	Amines from trigonella foemum - graecum
CN105481784A (zh) *	2015-12-28	2016-04-13	徐静	一种高含量苏式三唑醇的制备方法
CN107628935A (zh) *	2017-09-27	2018-01-26	南通利奥化工科技有限公司	一种二氯频哪酮的生产方法
JP7782851B2 (ja) *	2020-11-09	2025-12-09	国立大学法人鹿児島大学	ペプチド架橋剤及び当該架橋剤で架橋された架橋ペプチド
CN112961043B (zh) *	2021-03-12	2023-06-23	重庆医科大学	无溶剂条件制备α,α-二氯代酮

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DE2324010C3 (de) *	1973-05-12	1981-10-08	Bayer Ag, 5090 Leverkusen	1-Substituierte 2-Triazolyl-2-phenoxyäthanol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Pilzen
DE2743767A1 (de) *	1977-09-29	1979-04-12	Bayer Ag	Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
GR78217B (da) *	1981-07-02	1984-09-26	Ciba Geigy Ag
GB2102796A (en) *	1981-07-15	1983-02-09	Ici Plc	Fungicidal triazole and imidazole derivatives
DE3242252A1 (de) *	1982-11-15	1984-05-17	Bayer Ag, 5090 Leverkusen	Heterocyclisch substituierte hydroxyalkyl-azolyl-derivate

1984
- 1984-07-20 DE DE19843426906 patent/DE3426906A1/de not_active Withdrawn
1985
- 1985-07-10 AT AT85108573T patent/ATE45569T1/de not_active IP Right Cessation
- 1985-07-10 EP EP85108573A patent/EP0169439B1/de not_active Expired
- 1985-07-10 DE DE8585108573T patent/DE3572352D1/de not_active Expired
- 1985-07-17 IL IL75832A patent/IL75832A/xx unknown
- 1985-07-18 DD DD85278737A patent/DD237836A5/de unknown
- 1985-07-18 CA CA000487007A patent/CA1250585A/en not_active Expired
- 1985-07-19 HU HU852776A patent/HUT39167A/hu unknown
- 1985-07-19 BR BR8503453A patent/BR8503453A/pt unknown
- 1985-07-19 JP JP60158503A patent/JPS6176466A/ja active Pending
- 1985-07-19 DK DK330885A patent/DK330885A/da not_active Application Discontinuation
- 1985-07-19 KR KR1019850005156A patent/KR860001079A/ko not_active Withdrawn
- 1985-07-19 ZA ZA855466A patent/ZA855466B/xx unknown
- 1985-07-19 US US06/757,052 patent/US4751312A/en not_active Expired - Fee Related
- 1985-07-23 CN CN198585105611A patent/CN85105611A/zh active Pending

Also Published As

Publication number	Publication date
IL75832A0 (en)	1985-11-29
US4751312A (en)	1988-06-14
HUT39167A (en)	1986-08-28
EP0169439B1 (de)	1989-08-16
DK330885A (da)	1986-01-21
DE3426906A1 (de)	1986-01-30
CA1250585A (en)	1989-02-28
ZA855466B (en)	1986-03-26
EP0169439A2 (de)	1986-01-29
IL75832A (en)	1988-11-15
KR860001079A (ko)	1986-02-22
CN85105611A (zh)	1987-01-28
EP0169439A3 (en)	1987-05-27
JPS6176466A (ja)	1986-04-18
ATE45569T1 (de)	1989-09-15
BR8503453A (pt)	1986-04-15
DK330885D0 (da)	1985-07-19
DE3572352D1 (en)	1989-09-21

Publication	Publication Date	Title
EP0124009B1 (de)	1988-11-02	Verfahren zur Herstellung von Oxiranen
EP0143384B1 (de)	1989-04-05	Verfahren zur Herstellung von Beta-Hydroxyethyl-(1,2,4-triazol)-Derivaten
EP0054865A1 (de)	1982-06-30	Substituierte 1-Azolyl-butan-2-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide sowie als Zwischenprodukte
EP0560109B1 (de)	1996-07-17	Verfahren zur Herstellung von 1-Fluorcyclopropyl-methyl-keton
DD237836A5 (de)	1986-07-30	Verfahren zur synthese der diastereomeren formen von triazolyl-o,n-acetalen
EP0124013B1 (de)	1988-07-13	Verfahren zur Herstellung von Oxiranen
DE4030061A1 (de)	1991-12-19	Verfahren zur herstellung von benzylketonen sowie verfahren zur herstellung eines oxiranes
EP0124014B1 (de)	1988-10-05	Verfahren zur Herstellung von Oxiranen
US4962278A (en)	1990-10-09	Novel azole derivative and agricultural/horticultural fungicide containing said derivative as active ingredient
EP0063099A2 (de)	1982-10-20	Verfahren zur Herstellung von Phenyläthyltriazolen
EP0143379B1 (de)	1988-03-30	Verfahren zur Herstellung von beta-Hydroxyethyl-(1,2,4-triazol)-Derivaten
EP0260521A1 (de)	1988-03-23	Verfahren zur Herstellung von 4-substituierten 1-Aryl-5-amino-pyrazolen
EP0042980A2 (de)	1982-01-06	4-Substituierte 1-Azolyl-l-phenoxy-3,3-dimethyl-butan-2-one und -ole, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide
EP0048372B1 (de)	1983-10-26	Verfahren zur Herstellung von Pyrazol
DE3021516C2 (da)	1989-11-09
EP0132730A1 (de)	1985-02-13	3-(1,2,4-Triazol-1-yl)-1-propene
EP0046532B1 (de)	1983-09-14	3,3-Dimethyl-1-fluor-1-phenoxy-2-butanone(ole), Verfahren zu ihrer Herstellung und ihre Verwendung
EP0015456A1 (de)	1980-09-17	Omega-Halogen-acetophenon-oximether, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Zwischenprodukte zur Herstellung von omega-Azolyl-acetophenon-oximethern
EP0069754B1 (de)	1984-10-10	Verfahren zur herstellung von imidazolylvinylethern
EP0431450B1 (de)	1994-04-13	1-Brom-3-chlor-1,2-diaryl-2-propanole, Verfahren zur stereoselektiven Herstellung der erythro-1-Brom-3-chlor-1,2-diaryl-2-propanole und deren Umsetzung zu Azolylmethyloxiranen
EP0096801B1 (de)	1987-09-09	Azolylmethyl-ketone, Verfahren zu ihrer Herstellung und ihre Verwendung als Zwischenprodukte
EP0349856A2 (de)	1990-01-10	Optisch aktive Oxirane
DE69210717T2 (de)	1996-10-31	1,3,2-Dioxathiolan-S-Oxidderivate, ihre Verwendung als Fungizide und als Zwischenprodukte
EP0290903A2 (de)	1988-11-17	Beta-Fluoracyl-beta-halogenvinylalkylether
EP0060222A1 (de)	1982-09-15	Halogenmethyltriazole