KR900011745A - 할로겐화 공정 - Google Patents
할로겐화 공정 Download PDFInfo
- Publication number
- KR900011745A KR900011745A KR1019900000555A KR900000555A KR900011745A KR 900011745 A KR900011745 A KR 900011745A KR 1019900000555 A KR1019900000555 A KR 1019900000555A KR 900000555 A KR900000555 A KR 900000555A KR 900011745 A KR900011745 A KR 900011745A
- Authority
- KR
- South Korea
- Prior art keywords
- halo
- alkyl
- substituted
- alkoxy
- starting material
- Prior art date
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- 238000000034 method Methods 0.000 title claims 9
- 230000026030 halogenation Effects 0.000 title 1
- 238000005658 halogenation reaction Methods 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims 9
- 239000007858 starting material Substances 0.000 claims 7
- -1 hydroxy-substituted nitrogen Chemical class 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical class C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- GVRRXASZZAKBMN-UHFFFAOYSA-N 4-chloroquinazoline Chemical compound C1=CC=C2C(Cl)=NC=NC2=C1 GVRRXASZZAKBMN-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 claims 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
- C07D243/34—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings containing a quinazoline or hydrogenated quinazoline ring system
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 환 질소원자에 인접한 환 위치에서 하이드록시-치환된는 질소-함유 헤테로사이클릭 출발물질을 반응형태(Kinetic from)의 일반식(1)의 트리페닐포스파이트-할로겐 복합체와 반응시킴을 특징으로하는, 환 질소원자에 인접한 환 위치에서 클로로 또는 브로모 치환되는 질소-함유 헤테로사이클릭 화합물의 제조방법.상기식에서,Q는 H,할로,(C1-C4)알킬 또는 (C1-C4)알콕시이고, X는 C1 또는 Br이다.
- 제1항에 있어서, 트리페닐포스파이트-할로겐 복합체를 하이드록시-치환된 헤테로사이클릭 출발물질의 존재하에 제조하는 방법.
- 제1항에 있어서, 반응을 3급 아민 염기의 존재하에 수행하는 방법.
- 제1항에 있어서, 하이드록시-치환된 출발물질 1몰당 트리페닐포스파이트-할로겐 복합체 1내지1.3당량을 사용하는 방법.
- 제1항에 있어서, 질소-함유 헤테로사이클릭 출발물질이 임의로 치환된 4-하이드록시퀴나졸린인 방법.
- 제5항에 있어서, 임의로 치환된 4-하이드록시퀴나졸린 출발물질이 일반식(2)의 화합물인 방법.상기식에서,R1내지R4는 독립적으로 H, 할로,(C1-C4)알킬,측쇄(C3-C4)알킬,할로(C1-C4)알킬,할로(C1-C4)알콕시,(C1-C4)알콕시,할로(C1-C4)알킬티오,(C1-C4)알킬티오,또는 NO2이고,R1내지R4중 적어도 두 개는 H이며,Z＇는 H,CI,CH₃또는 OCH₃이다.
- 제6항에 있어서,출발물질이 4-하이드록시퀴나졸린인 방법.
- (a) 일반식(2)의 4-하이드록시퀴나졸린을 30℃ 이하의 온도하 불활성 유기용매 중에서, 일반식(Ⅰ)의 할로겐화 시약 1내지 1.3당량과 반응시키고, (b) 단계 (a)에서 생성된 4-클로로퀴나졸린을 분리시키지 않고,이를 일반식 (5a) 또는 (5b)의 알코올과 반응시키거나, 일반식(6)의 아민과 반응시킴을 특징으로 하는, 일반식(3)의 화합물 또는 일반식(1) 화합물의 산부가염의 제조방법.HO-Alk (5a)HO-W-Ar (5b)HNR7-W-Ar (6)상기식에서, R1내지 R4는 독립적으로 H, 할로 C1-C4)알킬, 측쇄(C3-C4)알킬, 할로(C1-C4)알킬, 할로(C1-C4)알콕시, (C1-C4)알콕시, 할로(C1-C4)알킬티오, (C1-C4)알킬티오, 또는 NO2이고 R1내지 R4중 적어도 두 개는 H이며, Y는 O-Alk, O-W-Ar,또는 NR7-W-Ar이고, Z는 H,Cl, OCH3, CH3, CCl3, 또는 -NR7-W-Ar이며, 단 Y가 -NR7-W-Ar인 경우에만 Z는 -NR7-W-Ar일수 있고, R|7은 H, 또는 (C1-C4)알킬이며, W는 산소, S, SO, SO2또는 NR7그룹을 임의로 포함하거나 3내지 7개의 탄소원자를 함유하는 포화 또는 불포화 카보사이클릭 환을 포함하거나, (C1-C3)알킬, (C2-C4)알케닐, 페닐, (C3-C8)사이클로알킬, 할로, 또는 아세틸로 치환되는, 탄소수 2내지 8의 알킬렌쇄이고, Ar은 이미다졸릴; 인돌릴; CH3또는 Cl로 임의 치환된 티에닐: 티아졸릴: 1,3-벤조디옥솔릴: 플루오레닐: 사이클로벤틸: 1-메틸사이클로펜틸: 사이클로헥실(헥사하이드로페닐): 사이클로헥세닐(테트라하이드로페닐): 나프틸: 디하이드로나프틸:테트라하이드로나프틸: 데카하이드로나프틸: 피리딜: 또는 일반식[여기에서, R10내지 R14는 독립적으로 H, 할로, I, (C₁-C10)알킬, 측쇄(C3-C6)알킬, 할로(C1-C4)알킬, (C1-C4)알콕시, 할로(C1-C4)알콕시, 페녹시, 치환된 페녹시, 페닐, 치환된 페닐, 페닐티오, 치환된 페닐티오, NO2, 아세톡시, CN, SiR15R16R17, OSiR15R16R17(여기서, R15,R16및 R17은 독립적으로 (C1-C4)알킬, (C1-C4)측쇄알킬, 페닐, 또는 치환된 페닐이다)이며, R10내지 R14중 적어도 두 개는 H이다]의 그룹이고, Alk는 할로, 할로C1-C4)알콕시, (C3-C8)사이클로알킬, 하이드록시, 또는 (C1-C4)아실로 임의 치환된, 직쇄 또는 측쇄의 ( C2-C18)포화 또는 불포화 탄화수소 쇄이며, Z'는 H, Cl, CH3, 또는 OCH3이고, Q는 H, 할로, (C1-C4)알킬, 또는 (C1-C4)알콕시이며, X는 Cl 또는 Br이다.
- 제8항에 있어서, 일반식(2)의 출발물질이 4-하이드록시퀴나졸린인 방법.
- 제9항에 있어서, 단계(b)가, 4-클로로퀴나졸린을 4-(3급-부틸)벤젤에탄올과 반응시킴을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30063389A | 1989-01-23 | 1989-01-23 | |
| US07/300.633 | 1989-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900011745A true KR900011745A (ko) | 1990-08-02 |
Family
ID=23159935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900000555A KR900011745A (ko) | 1989-01-23 | 1990-01-18 | 할로겐화 공정 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0380264A3 (ko) |
| JP (1) | JPH02258731A (ko) |
| KR (1) | KR900011745A (ko) |
| BR (1) | BR9000242A (ko) |
| CA (1) | CA2008079A1 (ko) |
| HU (1) | HUT52471A (ko) |
| IE (1) | IE900232L (ko) |
| IL (1) | IL93096A0 (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2769897A (en) * | 1996-05-07 | 1997-11-26 | Basf Aktiengesellschaft | Imidazoquinazolines, agents containing them and their use to combat fungi and animal pests |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230644A (en) * | 1979-02-01 | 1980-10-28 | Eli Lilly And Company | Halogenating reagents |
| US4510307A (en) * | 1980-08-20 | 1985-04-09 | Asahi Kasei Kogyo Kabushiki Kaisha | 6-Quinazolinesulfonyl derivatives and process for preparation thereof |
| IL89027A (en) * | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Quinazoline derivatives, process for their preparation and fungicidal, insecticidal and miticidal compositions containing them |
-
1990
- 1990-01-18 CA CA002008079A patent/CA2008079A1/en not_active Abandoned
- 1990-01-18 IL IL93096A patent/IL93096A0/xx unknown
- 1990-01-18 KR KR1019900000555A patent/KR900011745A/ko not_active Application Discontinuation
- 1990-01-18 JP JP2009479A patent/JPH02258731A/ja active Pending
- 1990-01-22 HU HU90229A patent/HUT52471A/hu unknown
- 1990-01-22 BR BR909000242A patent/BR9000242A/pt unknown
- 1990-01-22 IE IE900232A patent/IE900232L/xx unknown
- 1990-01-22 EP EP19900300625 patent/EP0380264A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IL93096A0 (en) | 1990-11-05 |
| EP0380264A3 (en) | 1991-02-06 |
| CA2008079A1 (en) | 1990-07-23 |
| JPH02258731A (ja) | 1990-10-19 |
| IE900232L (en) | 1990-07-23 |
| HUT52471A (en) | 1990-07-28 |
| BR9000242A (pt) | 1990-11-20 |
| HU900229D0 (en) | 1990-03-28 |
| EP0380264A2 (en) | 1990-08-01 |
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