NL2035261B1 - Synthetic method for 3,4-dihydroisoquinolin-1-one compounds - Google Patents
Synthetic method for 3,4-dihydroisoquinolin-1-one compounds Download PDFInfo
- Publication number
- NL2035261B1 NL2035261B1 NL2035261A NL2035261A NL2035261B1 NL 2035261 B1 NL2035261 B1 NL 2035261B1 NL 2035261 A NL2035261 A NL 2035261A NL 2035261 A NL2035261 A NL 2035261A NL 2035261 B1 NL2035261 B1 NL 2035261B1
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- compound
- synthesizing
- dihydroisoquinoline
- compounds according
- Prior art date
Links
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical class C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 title claims description 10
- 238000010189 synthetic method Methods 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 230000004224 protection Effects 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229930192474 thiophene Natural products 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 34
- 238000012512 characterization method Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- -1 3,4-DIHYDROISOQUINOLIN-1-ONE COMPOUNDS Chemical class 0.000 description 4
- 238000011160 research Methods 0.000 description 3
- MQKFSXLBPPCAGR-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydro-2h-isoquinolin-1-one Chemical compound C1CNC(=O)C2=C1C=C(OC)C(OC)=C2 MQKFSXLBPPCAGR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WPKMGEQXTYQXGI-UHFFFAOYSA-N thalifolin Chemical compound C1CN(C)C(=O)C2=C1C=C(OC)C(O)=C2 WPKMGEQXTYQXGI-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- BMHZAHGTGIZZCT-LJQANCHMSA-N (4r)-2-[(4-bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone Chemical compound C1([C@]2(C(NC(=O)C2)=O)C2=O)=CC(F)=CC=C1C(=O)N2CC1=CC=C(Br)C=C1F BMHZAHGTGIZZCT-LJQANCHMSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- SBFSGQVISGZPJH-UHFFFAOYSA-N Doryphornine Natural products C1=CN(C)C(=O)C2=C1C=C(OC)C(O)=C2 SBFSGQVISGZPJH-UHFFFAOYSA-N 0.000 description 1
- 241000725303 Human immunodeficiency virus Species 0.000 description 1
- LZAZURSABQIKGB-AEKGRLRDSA-N Narciclasine Chemical compound C1=C2C3=C[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=C(O)C2=C1OCO2 LZAZURSABQIKGB-AEKGRLRDSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 238000012966 insertion method Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229950002259 minalrestat Drugs 0.000 description 1
- VSEJCXBFXFEXPW-UHFFFAOYSA-N narciclasine Natural products OC1CC2=C(C(O)C1O)c3cc4OCOc4c(O)c3C(=O)N2 VSEJCXBFXFEXPW-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (7)
1. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on-verbindingen, omvattende de volgende stappen:
Sl. onder bescherming van inert gas, oplossen van een verbinding zoals weergegeven in formule (I) in een aprotisch oplosmiddel, en achtereenvolgens toevoegen van 1-2 mol/L tetrahydrofuranoplosmid- del van alkali en een verbinding zoals weergegeven in formule (II) onder roeren; en
S2. laten reageren onder verhittingsomstandigheden, en vervolgens een verbinding verzamelen zoals weergegeven in formule (III) uit het reactieproduct; o ? Al a SN aS rel N RY + Fy ss “Ri Cost An LA =~ Da Le U i {uy waarbij aromatische groepen in formule (I) en formule (II) zijn gekozen uit één van fenyl, gesubstitueerd fenyl, naftyl, pyridine, furan en thiofeen.
2. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on verbindingen volgens conclusie 1, waarbij in S2 de temperatuur van de reactie onder de verhittingsomstandigheden 60-100°C is en de reactietijd 12-16 uur is.
3. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on verbindingen volgens conclusie 2, waarbij in S1 de alkali wordt gekozen uit natriumbis(trimethylsilyl)amide.
4. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on verbindingen volgens conclusie 3, waarbij in Sl een molaire verhouding van de verbinding met formule (I) tot de verbinding met formule (II) tot de base is 1: 1-2: 2-3.
5. Werkwijze voor het synthetiseren van 3,4-dihydroisochincline-1- on verbindingen volgens conclusie 4, waarbij in 31 het aprotische oplosmiddel wordt gekozen uit elk van 1,4-dioxaan, cyclopentylme- thylether, tolueen, tetrahydrofuran en dimethoxyethaan.
6. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on verbindingen volgens conclusie 5, waarbij in S1 het inerte gas stikstofgas is.
7. Werkwijze voor het synthetiseren van 3,4-dihydroisochinoline-1- on verbindingen volgens conclusie 6, waarbij S2 de volgende stap- pen omvat: S201. reactie onder verhitting mogelijk maken; S202. water toevoegen om te blussen; S203. het filteren van het reactieproduct met silicagelpoeder en watervrij natrium; en S204. het uitvoeren van verdamping onder verlaagde druk na het wassen van het reactieproduct met ethylacetaat, en het scheiden van het mengsel met behulp van kolomchromatografie (PE: EA=10:1- 3:2) om een verbinding te verkrijgen zoals getoond in formule (III).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210813202.2A CN115093369B (zh) | 2022-07-12 | 2022-07-12 | 一种3,4-二氢异喹啉-1-酮类化合物的合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NL2035261A NL2035261A (en) | 2024-01-25 |
| NL2035261B1 true NL2035261B1 (en) | 2024-03-19 |
Family
ID=83296948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL2035261A NL2035261B1 (en) | 2022-07-12 | 2023-07-04 | Synthetic method for 3,4-dihydroisoquinolin-1-one compounds |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN115093369B (nl) |
| NL (1) | NL2035261B1 (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115819208B (zh) * | 2022-12-07 | 2023-12-12 | 浙大城市学院 | 一种2-芳基-3,4-二氢-1(2h)-萘酮类化合物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584830A (zh) * | 2011-12-30 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 二氢化茚酰胺化合物、其药物组合物及其用途 |
| CN110240590A (zh) * | 2019-07-16 | 2019-09-17 | 广州新民培林医药科技有限公司 | 一类嘧啶喹啉衍生物及其制备方法和应用 |
| CN112876419A (zh) * | 2019-11-29 | 2021-06-01 | 四川科伦博泰生物医药股份有限公司 | 烯丙胺衍生物及其制备方法和用途 |
-
2022
- 2022-07-12 CN CN202210813202.2A patent/CN115093369B/zh active Active
-
2023
- 2023-07-04 NL NL2035261A patent/NL2035261B1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL2035261A (en) | 2024-01-25 |
| CN115093369B (zh) | 2024-05-10 |
| CN115093369A (zh) | 2022-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NL2035261B1 (en) | Synthetic method for 3,4-dihydroisoquinolin-1-one compounds | |
| US20020099225A1 (en) | Efficient ligand-mediated ullmann coupling of anilnies and azoles | |
| CN103304437B (zh) | 一种无叠氮合成磷酸奥司他韦的方法 | |
| CN102153557A (zh) | 具有乙二胺骨架的多手性中心氮杂环卡宾前体盐、合成方法及用途 | |
| CN110818631B (zh) | 一种吡啶硫脲衍生物及其制备方法和应用 | |
| CN111646964A (zh) | 一种碱催化的合成2h-吡喃-2-酮衍生物新方法 | |
| CN110437128B (zh) | 一种3-硫醚基异吲哚啉酮类化合物的合成方法 | |
| CN101081851B (zh) | 一种α-氮杂螺环类药物模板的制备方法 | |
| CN103709221B (zh) | 一种虫草素的制备方法 | |
| KR830005164A (ko) | 이종원자고리화합물의 제조방법 및 이의 조성물 | |
| DE2530516A1 (de) | Verfahren zur herstellung von thieno eckige klammer auf 3,2-c eckige klammer zu pyridin und thieno eckige klammer auf 2,3-c eckige klammer zu pyridin | |
| CN109851544A (zh) | 一种多取代吡咯化合物的制备方法 | |
| CN104610075B (zh) | 一种4‑氨基‑1‑丁醇的合成方法 | |
| RU2291150C1 (ru) | Способ получения 5-ацил-пергидро-1,3,5-дитиазинов | |
| EP0299586A2 (en) | Process for preparing thiophene derivatives | |
| EP1157983A1 (de) | Verfahren zur Herstellung von Arylethylaminen durch Aminierung von Arylolefinen | |
| CN111116420A (zh) | 一种对称脲类化合物的制备方法 | |
| CN111072611B (zh) | 一种苯并呋喃亚胺内酯衍生物的合成方法 | |
| CN109851532A (zh) | 稀土胺化物在催化氮杂亨利反应中的应用 | |
| KR101221817B1 (ko) | 신규한 바이크로멘, 바이퀴놀린 유도체와 이의 제조방법 | |
| CN115477613B (zh) | 一种合成2-氨基咪唑啉类化合物的方法 | |
| CN115819208B (zh) | 一种2-芳基-3,4-二氢-1(2h)-萘酮类化合物的合成方法 | |
| CN109232330B (zh) | 一种苯磺酰氯类化合物与三乙胺无金属催化合成苯磺酰胺类化合物的方法 | |
| CN104529898A (zh) | 氮杂二苯并环辛炔类化合物及其制备方法 | |
| CN109867658B (zh) | 一种3-胺基噻吩衍生物及其合成方法 |