KR960034172A - 치환된 1,2,3,4-테트라히드로카르바졸의 제조 방법 - Google Patents
치환된 1,2,3,4-테트라히드로카르바졸의 제조 방법 Download PDFInfo
- Publication number
- KR960034172A KR960034172A KR1019960005674A KR19960005674A KR960034172A KR 960034172 A KR960034172 A KR 960034172A KR 1019960005674 A KR1019960005674 A KR 1019960005674A KR 19960005674 A KR19960005674 A KR 19960005674A KR 960034172 A KR960034172 A KR 960034172A
- Authority
- KR
- South Korea
- Prior art keywords
- process according
- bar
- hydrogenation
- general formula
- alkyl
- Prior art date
Links
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title abstract 2
- 150000002989 phenols Chemical class 0.000 claims abstract 3
- 230000002378 acidificating effect Effects 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 8
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- -1 phenol hydrazone Chemical class 0.000 claims 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 2
- 229940067157 phenylhydrazine Drugs 0.000 claims 2
- YAPRWCFMWHUXRS-UHFFFAOYSA-N (2-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=CC=C1O YAPRWCFMWHUXRS-UHFFFAOYSA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229910021538 borax Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
- 150000004031 phenylhydrazines Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000004328 sodium tetraborate Substances 0.000 claims 1
- 235000010339 sodium tetraborate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 150000007857 hydrazones Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
Abstract
하기 일반식(Ⅰ)의 치환된 1,2,3,4-테트라히드로카르바졸은 하기 일반식(Ⅱ)의 치환된 페놀을 촉매적으로 수소화하고, 수소화 용액을 하기 일반식(Ⅱ)의 페닐히드라진과 반응시켜 히드라존을 얻고, 얻어진 히드라존을 산성 조건 하에서 고리화함으로써 제조될 수 있다.
상기 일반식에서 R1내지 R8은 상기 명세서에서 나타난 것과 동일한 의미를 갖는다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
1종 이상의 에테르 용매 중에서, 임의로 지지체에 적용되는, 원소 주기율표(멘델레프)의 Ⅷ족의 일련의 금속 중에서 선택되는 촉배 존재 하, 및 필요에 따라 일련의 알칼리 반응성 알칼리 (토)금속 또는 암모늄염 중의 하나 이상의 추가의 첨가제 존재 하에서 하기 일반식(Ⅱ)의 치환 페놀을 촉매적으로 수소화하고, 촉매를 제거한 후 얻어진 수소화 용액을, 필요에 따라 물을 첨가한 후, 하기 일반식(Ⅲ)의 페닐히드라진과 반응시키고, 이 공정에서 얻어진 치환된 페놀히드로존 중간체를, 바람직하게 중간체 단리 후, 산성 조건 하에서 분자내 고리화시키는 것을 특징으로 하는 하기 일반식(Ⅰ)의 치환된 1,2,3,4-테트라히드로카르바졸의 제조 방법.
상기 일반식에서, R1, R2, R3, 및 R4는 서로 독립적으로 수소, C1-C4알킬, C3-C8-시클로알킬, 할로겐, 히드록실, C1-C4-알콕시, C3-C8-시클로알콕시, C1-C4-알킬아미노, N(C1-C4-알킬)2-, NH-C1-C4-아실, COOH, -COOC1-C4-알킬 또는 -CH2-Q를 나타내고, 여기에서 Q는 히드록실, C1-C4-알콕시 또는 NH-C1-C4-아실이고, R1내지 R4중 적어도 하나는 수소가 아니고, R5, R6, R7 , R 8은 서로 독립적으로 수소, C1-C4-알킬, 할로겐 또는 C1-C4-알콕시이다.
제1항에 있어서, 수소화가 디에틸렌 글리콜 디메틸, 에테르, 에틸렌 글리콜 에테르, 1.4-디옥산, 테트라 히드로푸란 또는 이들 혼합물 중에서 수행되는 것인 제조 방법.
제1항에 있어서, 사용된 치환된 페놀이 히드로퀴논, 4-메톡시-페놀 또는 p-아세틸아미노-페놀인 제조 제조 방법.
제1항에 있어서, 수소화가 20℃ 내지 250℃, 바람직하게는 60℃ 내지 230℃, 특히 바람직하게는 100℃ 내지 210℃의 온도 범위에서 수행되는 것인 제조 방법.
제1항에 있어서, 수소화가 1바아 내지 200바아, 바람직하게는 2바아 내지 150바아, 특히 바람직하게는 3바아 내지 100바아의 입력 범위에서 수행되는 것인 제조 방법.
제1항에 있어서, 사용된 촉매가 지지체, 바람직하게는 탄소 상의 팔라듐인 제조 방법.
제1항에 있어서, 수소화에 사용된 첨가제가 탄산나트륨 또는 붕사인 제조 방법.
제1항에 있어서, 비치환된 페닐히드라진이 사용되는 제조 방법.
제1항에 있어서, 고리화 단계를 수행하는데 사용된 산이 물과 혼합된 1 내지 3개의 탄소 원자를 갖는 알칸카르복실산, 바람직하게는 아세트산 수용액인 제조 방법.
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19507751.2 | 1995-03-06 | ||
| DE19507751A DE19507751A1 (de) | 1995-03-06 | 1995-03-06 | Verfahren zur Herstellung von substituierten 1,2,3,4-Tetrahydrocarbazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960034172A true KR960034172A (ko) | 1996-10-22 |
Family
ID=7755747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960005674A KR960034172A (ko) | 1995-03-06 | 1996-03-05 | 치환된 1,2,3,4-테트라히드로카르바졸의 제조 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5648500A (ko) |
| EP (1) | EP0731092B1 (ko) |
| JP (1) | JPH08245586A (ko) |
| KR (1) | KR960034172A (ko) |
| CN (1) | CN1137521A (ko) |
| AT (1) | ATE165821T1 (ko) |
| CA (1) | CA2170828A1 (ko) |
| CZ (1) | CZ66596A3 (ko) |
| DE (2) | DE19507751A1 (ko) |
| ES (1) | ES2115409T3 (ko) |
| HU (1) | HUP9600551A2 (ko) |
| TW (1) | TW386079B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10026646A1 (de) * | 2000-05-29 | 2001-12-06 | Merck Patent Gmbh | Verfahren zur Herstellung von Indolen |
| CN101456840B (zh) * | 2009-01-06 | 2011-05-11 | 华中师范大学 | 具有光学活性的取代的四氢咔唑衍生物 |
| CN102249983A (zh) * | 2011-05-24 | 2011-11-23 | 南通海迪化工有限公司 | 一种合成四氢咔唑类化合物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959309A (en) * | 1968-01-24 | 1976-05-25 | Sterling Drug Inc. | 3-Amido-1,2,3,4-tetrahydrocarbazoles |
| DE3431416A1 (de) * | 1984-08-27 | 1986-02-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 2-hydroxy-5,6,7,8-tetrahydrocarbazol, die alkali- und erdalkalisalze des 2-hydroxy-5,6,7,8-tetrahydrocarbazols und deren verwendung |
| DE3631824A1 (de) * | 1986-02-21 | 1988-03-31 | Bayer Ag | Cycloalkano(1.2-b)indol-sulfonamide |
| US4988820A (en) * | 1986-02-21 | 1991-01-29 | Bayer Aktiengesellschaft | Cycloalkano(1,2-B) indole-sulponamides |
-
1995
- 1995-03-06 DE DE19507751A patent/DE19507751A1/de not_active Withdrawn
-
1996
- 1996-01-31 TW TW085101162A patent/TW386079B/zh active
- 1996-02-22 AT AT96102651T patent/ATE165821T1/de not_active IP Right Cessation
- 1996-02-22 DE DE59600182T patent/DE59600182D1/de not_active Expired - Fee Related
- 1996-02-22 ES ES96102651T patent/ES2115409T3/es not_active Expired - Lifetime
- 1996-02-22 EP EP96102651A patent/EP0731092B1/de not_active Expired - Lifetime
- 1996-02-29 US US08/608,869 patent/US5648500A/en not_active Expired - Fee Related
- 1996-03-01 CA CA002170828A patent/CA2170828A1/en not_active Abandoned
- 1996-03-04 JP JP8070884A patent/JPH08245586A/ja active Pending
- 1996-03-05 HU HU9600551A patent/HUP9600551A2/hu unknown
- 1996-03-05 KR KR1019960005674A patent/KR960034172A/ko not_active Application Discontinuation
- 1996-03-05 CZ CZ96665A patent/CZ66596A3/cs unknown
- 1996-03-06 CN CN96104111A patent/CN1137521A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN1137521A (zh) | 1996-12-11 |
| EP0731092A1 (de) | 1996-09-11 |
| ES2115409T3 (es) | 1998-06-16 |
| DE19507751A1 (de) | 1996-09-12 |
| JPH08245586A (ja) | 1996-09-24 |
| CZ66596A3 (en) | 1996-09-11 |
| TW386079B (en) | 2000-04-01 |
| HU9600551D0 (en) | 1996-04-29 |
| CA2170828A1 (en) | 1996-09-07 |
| DE59600182D1 (de) | 1998-06-10 |
| HUP9600551A2 (hu) | 1998-09-28 |
| US5648500A (en) | 1997-07-15 |
| EP0731092B1 (de) | 1998-05-06 |
| ATE165821T1 (de) | 1998-05-15 |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |