PL88728B1 - - Google Patents
Download PDFInfo
- Publication number
- PL88728B1 PL88728B1 PL17058874A PL17058874A PL88728B1 PL 88728 B1 PL88728 B1 PL 88728B1 PL 17058874 A PL17058874 A PL 17058874A PL 17058874 A PL17058874 A PL 17058874A PL 88728 B1 PL88728 B1 PL 88728B1
- Authority
- PL
- Poland
- Prior art keywords
- phthalazine
- mixture
- dione
- dioxane
- tetrahydrofuran
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 22
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- YSZIOXAEADAJLX-UHFFFAOYSA-N phthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)N=NC(=O)C2=C1 YSZIOXAEADAJLX-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- DRTWNJQJYUBAMQ-UHFFFAOYSA-N phthalazino[2,3-b]phthalazine Chemical compound C1=CC=CC2=CN3N(C=C4C=CC=CC4=C3)C=C12 DRTWNJQJYUBAMQ-UHFFFAOYSA-N 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960001701 chloroform Drugs 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VOYADQIFGGIKAT-UHFFFAOYSA-N 1,3-dibutyl-4-hydroxy-2,6-dioxopyrimidine-5-carboximidamide Chemical compound CCCCn1c(O)c(C(N)=N)c(=O)n(CCCC)c1=O VOYADQIFGGIKAT-UHFFFAOYSA-N 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 0 CCCC(c1ccccc1C(*C1CC=C)*=*)N1C(c1c(CC)cccc1)=O Chemical compound CCCC(c1ccccc1C(*C1CC=C)*=*)N1C(c1c(CC)cccc1)=O 0.000 description 1
- JKGOVRUQVOXRKF-UHFFFAOYSA-N C[N](C(c1c2cccc1)=[O-])(C(c1ccccc1C1)=O)N1C21[IH]C1 Chemical compound C[N](C(c1c2cccc1)=[O-])(C(c1ccccc1C1)=O)N1C21[IH]C1 JKGOVRUQVOXRKF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 ethylene glycol dialkyl ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2019873 | 1973-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL88728B1 true PL88728B1 (cs) | 1976-09-30 |
Family
ID=10142038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17058874A PL88728B1 (cs) | 1973-04-27 | 1974-04-25 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5221518B2 (cs) |
| AR (1) | AR198570A1 (cs) |
| CA (1) | CA1014556A (cs) |
| CH (1) | CH587855A5 (cs) |
| CS (1) | CS176136B2 (cs) |
| DD (1) | DD111205A5 (cs) |
| ES (1) | ES425746A1 (cs) |
| HU (1) | HU167320B (cs) |
| NL (1) | NL156406B (cs) |
| PL (1) | PL88728B1 (cs) |
| SU (1) | SU518129A3 (cs) |
-
1974
- 1974-04-18 AR AR25334674A patent/AR198570A1/es active
- 1974-04-19 NL NL7405320A patent/NL156406B/xx unknown
- 1974-04-25 PL PL17058874A patent/PL88728B1/pl unknown
- 1974-04-25 CH CH569274A patent/CH587855A5/fr not_active IP Right Cessation
- 1974-04-26 HU HULE000743 patent/HU167320B/hu unknown
- 1974-04-26 CA CA198,253A patent/CA1014556A/en not_active Expired
- 1974-04-26 SU SU2018861A patent/SU518129A3/ru active
- 1974-04-26 JP JP4745274A patent/JPS5221518B2/ja not_active Expired
- 1974-04-26 CS CS300074A patent/CS176136B2/cs unknown
- 1974-04-26 DD DD17816074A patent/DD111205A5/xx unknown
- 1974-04-27 ES ES425746A patent/ES425746A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS176136B2 (cs) | 1977-06-30 |
| CA1014556A (en) | 1977-07-26 |
| HU167320B (cs) | 1975-09-27 |
| JPS5013397A (cs) | 1975-02-12 |
| NL156406B (nl) | 1978-04-17 |
| NL7405320A (cs) | 1974-10-29 |
| DD111205A5 (cs) | 1975-02-05 |
| JPS5221518B2 (cs) | 1977-06-10 |
| SU518129A3 (ru) | 1976-06-15 |
| ES425746A1 (es) | 1976-07-01 |
| CH587855A5 (en) | 1977-05-13 |
| AR198570A1 (es) | 1974-06-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fowler | Synthesis of 1, 2-and 1, 4-dihydropyridines | |
| US3609184A (en) | 1-substituted-3-indenylacetic acid and esters | |
| PL88728B1 (cs) | ||
| PL84115B3 (en) | 2-(furfuryl-methyl)-6,7-benzomorphans and acid addition salts thereof[us3823150a] | |
| US3167579A (en) | Substituted 4, 10-dioxo-5-hydroxy-1, 2, 3, 4, 4a, 9, 9a, 10-octahydroanthracenes | |
| US3891630A (en) | Substituted pyrazolo{8 3,4-e{9 {8 1,4{9 thiazepines and isoxazolo{8 5,4-e{9 {8 1,4{9 thiazepines | |
| US20030204095A1 (en) | Process for the preparation of thiazole intermediate | |
| JPS5927349B2 (ja) | ２，６−メタノ−２ｈ−１−ベンゾオキソシン類 | |
| EP0026505B1 (en) | 7,8-substituted-1-phenyl-2,3,4,5-tetrahydro-1-h-3-benzazepines | |
| KR101338297B1 (ko) | 2,9-디메틸-4,7-디페닐-1,10-페난트롤린의 단일 단계 합성방법 | |
| PL140035B1 (en) | Process for preparing novel derivatives of 8-carbonylamino-4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinoline | |
| Doi et al. | Regiospecificity in the cyclization of 6-(1-hydroxyalkyl) geraniol derivatives. A simple route to the taxol a-ring system | |
| Bishop et al. | The behaviour of unsaturated 1, 2-hydroxyiminoketones with trifluoroacetic acid | |
| IE46327B1 (en) | Carbocylic fused thiophen-2-oxaminic acid derivatives | |
| CN107673956A (zh) | 一种苯并环酮类化合物的制备方法 | |
| US3709947A (en) | 6-chloropropylidene-1,1a,6,10b-tetrahydrobenzo(a,e)cyclopropa(c)cycloheptenes | |
| Lempert-Sréter et al. | Electron deficient heteroaromatic ammonioamidates. Part 26. N-(quinazolin-3-io) amidates. Part 13. Phototransformations of an N-(quinazolin-3-io) thioamidate and of a 10b H-1, 3, 4-thiadiazolo [3, 2-c] quinazoline, the ring isomer of an N-(quinazolin-3-io) thioamidate, and the photochemical formation of some 4, 4′-biquinazolinyls | |
| Doyle | Cycloaddition reactions. Addition of dimethyl acetylenedicarboxylate to 1-dimethylaminoindene | |
| Korbonits et al. | Chemistry of the Heterocyclic Pseudobasic Amino Alcohols, XXXVIII Ring‐Chain Tautomerism of Pyrimido [6, 1‐a] isoquinolines | |
| CA1055944A (en) | 2-methyl-6-phenyl-1,2,3,4,4a,5,6,10b-octahydrobenzo-(c)-(1,6) naphthyridine compounds | |
| CA1038876A (en) | Benzocycloheptathiophene derivatives | |
| Amiya et al. | Commications-on anhydrodiacetyllucaconine (diacetyldelcosine, MP 159-161) and its derivatives | |
| US3432526A (en) | 5,9 - epoxy - 6,7,8,9 - tetrahydro - 5h - benzocyclohepten-5-ols and process for preparing same | |
| Tsolomitis et al. | The rearrangement of 2‐benzyl‐5‐mesitoyl‐3 (2H)‐isothiazolone to 2‐phenyl‐6‐mesitoyl‐3, 4‐dihydro‐1, 3‐thiazin‐4 (2H)‐one | |
| Hatta et al. | Preparation of [23] cyclophane‐1, 2‐diones by the reaction of 3, 6; 12, 15‐Di‐1, 4‐benzo [6.6](3, 4)‐1, 2, 5‐thiadiazolocyclophanes with grignard reagents |