KR950704279A - 2,4-옥사졸리딘디온의 제조 방법(Processes for Preparing 2,4-Oxazolidinediones) - Google Patents

2,4-옥사졸리딘디온의 제조 방법(Processes for Preparing 2,4-Oxazolidinediones)

Info

Publication number
KR950704279A
KR950704279A KR1019950701902A KR19950701902A KR950704279A KR 950704279 A KR950704279 A KR 950704279A KR 1019950701902 A KR1019950701902 A KR 1019950701902A KR 19950701902 A KR19950701902 A KR 19950701902A KR 950704279 A KR950704279 A KR 950704279A
Authority
KR
South Korea
Prior art keywords
formula
compound
phenyl
triazolyl
halogen
Prior art date
Application number
KR1019950701902A
Other languages
English (en)
Other versions
KR100269681B1 (en
Inventor
제프리 아서 스턴버그
깅-모 선
마수오 토지
빈센트 제라드 위터홀트
Original Assignee
미리암 디. 메코너헤이
이.아이. 듀폰 디 네모아 앤드 캄파니
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 미리암 디. 메코너헤이, 이.아이. 듀폰 디 네모아 앤드 캄파니 filed Critical 미리암 디. 메코너헤이
Publication of KR950704279A publication Critical patent/KR950704279A/ko
Application granted granted Critical
Publication of KR100269681B1 publication Critical patent/KR100269681B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/44—Two oxygen atoms
    • 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
    • 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
    • C07D233/60—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 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen 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

Landscapes

  • 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

본 발명은 2―하이드록시카르복실산 에스테르를 염기의 존재하에 카르보닐화제와 반응시킨 후, 산의 존재하에 페닐 히드라진과 반응시키는 것을 포함하는, 하기 일반식(I)의 1,4―옥사졸리딘디온의 제조 방법을 제공한다.
상기 식중, R1은 1―2개의 할로겐; 또는 각각의 페닐 고리 상에서 R2에 의해 임의로 치환된 4―페녹시, 4―(1―페넬틸옥시) 또는 4―벤질옥시에 의해 임의 치환된 페닐이고, R7는 할로겐, 메틸 또는 에틸이다.

Description

2,4―옥사졸리딘디온의 제조 방법(Processes for Preparing 2,4―Oxazolidiones)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

1)하기 일반식 II
의 2―히드록시카르복실산 에스테를 염기 및 하기 일반식 III
의 카르보닐화제의 반응시켜 하기 일반식 IV
의 중간체 화합물을 얻고: 2)상기한 일반식 IV의 화합물을 산의 존재하에 페닐히드라진과 반응시켜서 하기 일반식 I의 화합물을 얻는 것으로 이루어진, 하기 일반식 I의 2,4―옥사졸리딘 디온의 제조방법.
상기 식들중, R1은 1―2개의 할로겐; 또는 각각의 페닐 고리 상에서 R2에 의해 임의 치환된 4―페녹시, 4―(1―페네틸옥시) 또는 4―벤질옥시에 의해 치환된 페닐이고, R2는 할로겐, 메틸 또는 에틸이고, R3는 C1―C4알킬이고, Y는 1―이미다졸릴 또는 1,2,4―트리아졸릴이고, 단 일반식 II에 있는 R1이 4―(1―페네틸옥시) 또는 4―벤질옥시에 의해 치환된 페닐일 경우 Y는 1,2,4―트리아졸릴이다.
제1항에 있어서, 일반식 III의 Y가 1―이미다졸릴 또는 1,2,4―트리아졸릴이고, 일반식 II의 R1이 4―페녹시페닐 또는 2,4―디플루오로페닐인 것인 방법.
제1항에 있어서, 일반식 I의 생성물 중의 R1이 4―페녹시페닐인 것인 방법.
제1항에 있어서, 1)포스겐, 2)이미다졸 또는 1,2,4―트리아졸 중 하나, 및 3)트리알킬아민, 피리딘, 피콜린 또는 다른 치환 피리딘으로 이루어진 군으로부터 선택된 유기 염기를 반응시키거나; 1)포스겐 및 2)1,2,4―트리아졸의 알칼리 금속염을 반응시킴으로써 일반식 III의 카르보닐화제를 동일 반응계 내에서 제조하는 것을 더 포함하는 것인 방법.
제4항에 있어서, 일반식 III의 카르보닐화제가 포스겐 및 1,2,4―트리아졸의 알칼리 금속염을 반응시킴으로써 동일 반응계 내에서 제조되는 것인 방법.
제1항에 있어서, 일반식 IV의 화합물이 유기 염기로서 1종 이상의 피콜린을 사용하에 제조되는 것인 방법.
제6항에 있어서, 단계 1)의 반응 혼합물의 단계 2)에 앞서 여과시키는 것인 방법.
제7항에 있어서, 단계 2)에 사용된 산이 아세트산인 것인 방법.
하기 일반식 IV의 화합물
상기 식 중, R1은 1―2개의 할로겐; 또는 고리 상에 R2에 의해 임의 치환된 4―페녹시, 4―(1―페넬티옥시) 또는 4―벤질옥시에 의해 치환된 페닐이고, R2는 할로겐, 메틸 또는 에틸이고, R3은 C1―C4알킬이고, Y는 1―이미다졸릴 또는 1,2,4―트리아졸릴이다.
제9항에 있어서, R1이 4―페녹시페닐이고, Y가 1,2,4―트리아졸릴인 화합물.
※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019950701902A 1992-11-13 1995-05-12 Process for preparing 2,4-oxazolidinediones KR100269681B1 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US97613092A 1992-11-13 1992-11-13
US07/976130 1992-11-13
US98857492A 1992-12-10 1992-12-10
US07/988574 1992-12-10
US2323993A 1993-02-25 1993-02-25
US08/023239 1993-02-25
PCT/US1993/010435 WO1994011359A1 (en) 1992-11-13 1993-11-05 Processes for preparing 2,4-oxazolidinediones

Publications (2)

Publication Number Publication Date
KR950704279A true KR950704279A (ko) 1995-11-17
KR100269681B1 KR100269681B1 (en) 2000-10-16

Family

ID=27362036

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019950701902A KR100269681B1 (en) 1992-11-13 1995-05-12 Process for preparing 2,4-oxazolidinediones

Country Status (12)

Country Link
US (1) US5552554A (ko)
EP (1) EP0668859B1 (ko)
JP (1) JP3356286B2 (ko)
KR (1) KR100269681B1 (ko)
AT (1) ATE149157T1 (ko)
AU (1) AU674042B2 (ko)
BR (1) BR9307577A (ko)
DE (1) DE69308317T2 (ko)
ES (1) ES2098901T3 (ko)
HU (1) HU215699B (ko)
PL (1) PL177163B1 (ko)
WO (1) WO1994011359A1 (ko)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ296513B6 (cs) * 1995-07-12 2006-03-15 E. I. Du Pont De Nemours And Company Synergická fungicidní kompozice
GB9607784D0 (en) * 1996-04-15 1996-06-19 Zeneca Ltd Fungicides
WO1998031672A1 (en) * 1997-01-17 1998-07-23 Ppg Industries Ohio, Inc. Method of producing n,n'-diazole compounds
DE19830556A1 (de) 1998-07-08 2000-01-13 Basf Ag Verfahren zur Herstellung von Carbonyldiimidazolen
EP1092712A1 (en) * 1999-10-13 2001-04-18 E.I. Du Pont De Nemours And Company Process for preparing fungicidal oxazolidinones and imidazolinones
HUP0202516A3 (en) 2000-05-15 2003-04-28 Kaneka Corp Methods for crystallization of n-(1-(s)-ethoxycarbonyl-3-phenylpropyl)-l-alanine n-carboxyanhydride
KR101126954B1 (ko) * 2004-03-30 2012-03-23 호도가야 가가쿠 고교 가부시키가이샤 Ｎ,ｎ'-카르보닐디이미다졸의 제조 방법
CN103396410A (zh) * 2013-08-07 2013-11-20 北京金五元科技发展有限责任公司 吡噁唑菌酮的合成及作为农用杀菌剂的应用
CN107540626A (zh) * 2016-06-23 2018-01-05 华东理工大学 噁唑菌酮的多晶型及其制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3954992A (en) * 1973-07-02 1976-05-04 E. I. Du Pont De Nemours And Company 2-Cyano-2-hydroxyiminoacetamides as plant disease control agents
CH654979A5 (de) * 1982-01-26 1986-03-27 Sandoz Ag Fungizide und ihre verwendung.
US5356908A (en) * 1989-04-21 1994-10-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
DK0393911T3 (da) * 1989-04-21 1994-10-03 Du Pont Fungicide oxazolidinoner
US4957933A (en) * 1989-04-21 1990-09-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
WO1993018016A1 (en) * 1992-03-11 1993-09-16 E.I. Du Pont De Nemours And Company Fungicidal oxazolidinones
EP0637301A1 (en) * 1992-04-24 1995-02-08 E.I. Du Pont De Nemours And Company Fungicidal oxazolidinones
USH1401H (en) * 1993-11-15 1995-01-03 E. I. Du Pont De Nemours And Company, Inc. Fungicidal oxazolidinones

Also Published As

Publication number Publication date
AU674042B2 (en) 1996-12-05
AU5544094A (en) 1994-06-08
HU9500607D0 (en) 1995-04-28
HU215699B (hu) 1999-02-01
ES2098901T3 (es) 1997-05-01
EP0668859B1 (en) 1997-02-26
KR100269681B1 (en) 2000-10-16
US5552554A (en) 1996-09-03
HUT71639A (en) 1996-01-29
JPH08502994A (ja) 1996-04-02
ATE149157T1 (de) 1997-03-15
BR9307577A (pt) 1999-05-25
PL308908A1 (en) 1995-09-04
PL177163B1 (pl) 1999-09-30
WO1994011359A1 (en) 1994-05-26
EP0668859A1 (en) 1995-08-30
DE69308317D1 (de) 1997-04-03
DE69308317T2 (de) 1997-09-04
JP3356286B2 (ja) 2002-12-16

Similar Documents

Publication Publication Date Title
JPH0317071A (ja) ３―アミノ―５―アミノカルボニル―１，２，４―トリアゾール誘導体類の製造方法
KR950704279A (ko) 2,4-옥사졸리딘디온의 제조 방법(Processes for Preparing 2,4-Oxazolidinediones)
RU2588570C2 (ru) Способ получения хиральных гидразидов
KR870006018A (ko) 복소환식 화합물
CZ281655B6 (cs) Způsob přípravy derivátů 1-fenylimidazolin-2,5-dionu
CA2009480A1 (fr) Derives de pyrimidinyl-piperazinyl-alkyl azoles avec activite anxiolitique et/ou tranquillisante
KR860008988A (ko) 복소환식 화합물의 제법
KR840007589A (ko) 트리아졸 유도체의 제조방법
KR860007251A (ko) 트리아졸 유도체의 제조방법
SU497772A3 (ru) Способ получени замещенных 2-фениламино-имидазолинов-(2)
JPH051273B2 (ko)
KR870008860A (ko) 설포닐 아졸 및 그의 제조방법
RU2179552C2 (ru) СПОСОБ ПОЛУЧЕНИЯ ЭТИЛ-α-2-ДИХЛОР-5-[4-(ДИФТОРМЕТИЛ)-4,5-ДИГИДРО-3-МЕТИЛ-5-ОКСО-1H-1,2,4-ТР ИАЗОЛ-1-ИЛ]-4-ФТОРБЕНЗОЛПРОПИОНАТА
JPS60136573A (ja) １，２，４−トリアゾロン誘導体の製造方法
KR880011128A (ko) 1,5-디페닐 -1h-1,2,4-트라이졸 -3- 카르복시아미드 유도체 및 이를 함유하는 제초제 조성물
JPS60136571A (ja) β−ヒドロキシエチル−（１，２，４−トリアゾ−ル）誘導体の製造方法
US4835283A (en) 3,5-diphenyl-3-[(1H-imidazol-1-ylmethyl) or (1H-1,2,4-triazol-1-ylmethyl)]-2
GB1477277A (en) Process for the manufacture of heterocyclic substituted styrenes heterocyclic substituted styrenes and their use as optical brighteners
US5166378A (en) Selective monoacylation of substituted hydrazines
CA2190851C (en) Palladium catalyzed ring closure of triazolyl tryptamine
SK12392003A3 (sk) Spôsob prípravy monohydrátu a kryštalických modifikácií flukonazolu
JP2750960B2 (ja) ５−アルコキシヒダントイン類の製造方法
EP0296745A1 (en) Process for the isomerization of symmetric triazoles to unsymmetric triazoles
EP0812834B1 (en) Process for the preparation of 3-(substituted phenyl)-5-alkylidene-1,3-oxazolidine-2,4-dione derivatives
US4288598A (en) Pyridine-2,3,6-triones

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
G170 Re-publication after modification of scope of protection [patent]
FPAY Annual fee payment

Payment date: 20130618

Year of fee payment: 14

EXPY Expiration of term