MX376412B - Proceso para la preparación de compuestos de isoxazolina ópticamente activos. - Google Patents
Proceso para la preparación de compuestos de isoxazolina ópticamente activos.Info
- Publication number
- MX376412B MX376412B MX2017001707A MX2017001707A MX376412B MX 376412 B MX376412 B MX 376412B MX 2017001707 A MX2017001707 A MX 2017001707A MX 2017001707 A MX2017001707 A MX 2017001707A MX 376412 B MX376412 B MX 376412B
- Authority
- MX
- Mexico
- Prior art keywords
- sub
- preparation
- formula
- optically active
- isoxazoline compounds
- Prior art date
Links
- 150000002547 isoxazolines Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- 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
-
- 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
- C07D261/10—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención se refiere a un proceso para la preparación de un compuesto de fórmula (I) (ver Fórmula) donde A1 y A2 son C-H, o uno de A1 y A2 es C-H y el otro es N; R1 es alquilo C1-C4, haloalquilo C1-C4 o cicloalquilo C3-C6; cada R2 es independientemente bromo, cloro, flúor o trifluorometilo; R3 es hidrógeno; R4 es hidrógeno, halógeno, metilo, halometilo o ciano; o R3 y R4 juntos forman un grupo 1,3-butadieno que actúa como puente; R5 es clorodifluorometilo o trifluorometilo; n es 2 o 3; haciendo reaccionar un compuesto de fórmula (II) (ver Fórmula) donde A1, A2, R1, R2, R3, R4, R5 y n son como se han definido para la fórmula I anterior, con hidroxilamina, una base y un catalizador quiral, caracterizado por que el catalizador quiral es un catalizador dimérico quiral de fórmula (III) (ver Fórmula) donde R6, R7, R8, R9, R10 y X son como se han definido en la reivindicación 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14180467 | 2014-08-11 | ||
| EP15164843 | 2015-04-23 | ||
| PCT/EP2015/067894 WO2016023787A1 (en) | 2014-08-11 | 2015-08-04 | Process for the preparation of optically active isoxazoline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2017001707A MX2017001707A (es) | 2017-04-27 |
| MX376412B true MX376412B (es) | 2025-03-07 |
Family
ID=53761405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2017001707A MX376412B (es) | 2014-08-11 | 2015-08-04 | Proceso para la preparación de compuestos de isoxazolina ópticamente activos. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9815829B2 (es) |
| EP (1) | EP3180336B1 (es) |
| JP (1) | JP6541771B2 (es) |
| KR (1) | KR102497654B1 (es) |
| CN (1) | CN106661016B (es) |
| BR (1) | BR112017002507B1 (es) |
| DK (1) | DK3180336T3 (es) |
| ES (1) | ES2702193T3 (es) |
| HU (1) | HUE041438T2 (es) |
| IL (1) | IL250211B (es) |
| MX (1) | MX376412B (es) |
| PL (1) | PL3180336T3 (es) |
| SI (1) | SI3180336T1 (es) |
| TW (1) | TWI699362B (es) |
| WO (1) | WO2016023787A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201721235D0 (en) * | 2017-12-19 | 2018-01-31 | Syngenta Participations Ag | Polymorphs |
| CA3164924A1 (en) | 2019-12-18 | 2021-06-24 | Elanco Tiergesundheit Ag | Isoxazoline derivatives as pesticides |
| KR20230043904A (ko) * | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| PY2272949A (es) * | 2021-08-30 | 2023-04-28 | Syngenta Crop Prot Ag | Procedimiento para la preparación de un compuesto de isoxazolina ópticamente activo |
| IL317108A (en) | 2022-05-30 | 2025-01-01 | Syngenta Crop Protection Ag | Process for preparing 4-SUBSTITUTED 2-OXAZOLIDINONES |
| IL322407A (en) | 2023-02-24 | 2025-09-01 | Syngenta Crop Protection Ag | Process for preparing isoxazoline derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6596870B2 (en) * | 2000-07-13 | 2003-07-22 | Brandeis University | Asymmetric synthetic methods based on phase transfer catalysis |
| TWI487486B (zh) * | 2009-12-01 | 2015-06-11 | Syngenta Participations Ag | 以異唑啉衍生物為主之殺蟲化合物 |
| EA201201179A1 (ru) * | 2010-02-25 | 2013-04-30 | Зингента Партисипейшнс Аг | Способ получения изоксазолиновых производных |
| WO2011161130A1 (en) | 2010-06-23 | 2011-12-29 | Basf Se | Process for producing imine compounds for combating invertebrate pests |
| US9126995B2 (en) * | 2011-11-08 | 2015-09-08 | Nissan Chemical Industries, Ltd. | Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound |
-
2015
- 2015-08-04 PL PL15744256T patent/PL3180336T3/pl unknown
- 2015-08-04 WO PCT/EP2015/067894 patent/WO2016023787A1/en not_active Ceased
- 2015-08-04 EP EP15744256.7A patent/EP3180336B1/en active Active
- 2015-08-04 MX MX2017001707A patent/MX376412B/es active IP Right Grant
- 2015-08-04 JP JP2017506741A patent/JP6541771B2/ja active Active
- 2015-08-04 CN CN201580042943.3A patent/CN106661016B/zh active Active
- 2015-08-04 SI SI201530526T patent/SI3180336T1/sl unknown
- 2015-08-04 KR KR1020177003713A patent/KR102497654B1/ko active Active
- 2015-08-04 US US15/501,008 patent/US9815829B2/en active Active
- 2015-08-04 DK DK15744256.7T patent/DK3180336T3/en active
- 2015-08-04 BR BR112017002507-8A patent/BR112017002507B1/pt active IP Right Grant
- 2015-08-04 ES ES15744256T patent/ES2702193T3/es active Active
- 2015-08-04 HU HUE15744256A patent/HUE041438T2/hu unknown
- 2015-08-10 TW TW104125921A patent/TWI699362B/zh active
-
2017
- 2017-01-19 IL IL250211A patent/IL250211B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| BR112017002507A2 (pt) | 2019-10-22 |
| HUE041438T2 (hu) | 2019-05-28 |
| CN106661016A (zh) | 2017-05-10 |
| DK3180336T3 (en) | 2019-01-14 |
| EP3180336A1 (en) | 2017-06-21 |
| ES2702193T3 (es) | 2019-02-27 |
| US20170217953A1 (en) | 2017-08-03 |
| CN106661016B (zh) | 2020-02-14 |
| JP2017526665A (ja) | 2017-09-14 |
| MX2017001707A (es) | 2017-04-27 |
| IL250211A0 (en) | 2017-03-30 |
| JP6541771B2 (ja) | 2019-07-10 |
| EP3180336B1 (en) | 2018-09-26 |
| KR102497654B1 (ko) | 2023-02-08 |
| IL250211B (en) | 2019-06-30 |
| PL3180336T3 (pl) | 2019-05-31 |
| TW201612176A (en) | 2016-04-01 |
| WO2016023787A1 (en) | 2016-02-18 |
| BR112017002507B1 (pt) | 2021-05-04 |
| US9815829B2 (en) | 2017-11-14 |
| KR20170035937A (ko) | 2017-03-31 |
| TWI699362B (zh) | 2020-07-21 |
| SI3180336T1 (sl) | 2019-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |