SU414790A3 - СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2,3-ДИГИДРО-5Н-ИМИДАЗО[2,1-о]ИЗОИНДОЛА12 - Google Patents
СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2,3-ДИГИДРО-5Н-ИМИДАЗО[2,1-о]ИЗОИНДОЛА12Info
- Publication number
- SU414790A3 SU414790A3 SU1338547A SU1338547A SU414790A3 SU 414790 A3 SU414790 A3 SU 414790A3 SU 1338547 A SU1338547 A SU 1338547A SU 1338547 A SU1338547 A SU 1338547A SU 414790 A3 SU414790 A3 SU 414790A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- isoindole
- dihydro
- imidazo
- phenyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 18
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- -1 aziridinium tetrafluoroborate Chemical compound 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003570 air Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UVSYDEZIPVQBKW-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-ethoxy-1H-isoindole Chemical compound ClC=1C=C(C=CC1Cl)C1N=C(C2=CC=CC=C12)OCC UVSYDEZIPVQBKW-UHFFFAOYSA-N 0.000 description 2
- GIZZYXYMDUIPLS-UHFFFAOYSA-N 3-ethoxy-1-phenyl-1h-isoindole Chemical compound C12=CC=CC=C2C(OCC)=NC1C1=CC=CC=C1 GIZZYXYMDUIPLS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 150000002518 isoindoles Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- KUJOYSYDFXHSLA-UHFFFAOYSA-N 1h-isoindole;hydrochloride Chemical compound Cl.C1=CC=C2CN=CC2=C1 KUJOYSYDFXHSLA-UHFFFAOYSA-N 0.000 description 1
- ASUUTNHFPJIKFL-UHFFFAOYSA-N 3-ethoxy-1-(4-fluorophenyl)-1H-isoindole Chemical compound FC1=CC=C(C=C1)C1N=C(C2=CC=CC=C12)OCC ASUUTNHFPJIKFL-UHFFFAOYSA-N 0.000 description 1
- WSKBLLFHGABBEW-UHFFFAOYSA-N 3-phenyl-2,3-dihydroisoindol-1-one Chemical compound C12=CC=CC=C2C(=O)NC1C1=CC=CC=C1 WSKBLLFHGABBEW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- RTQCEQASWIGHNC-UHFFFAOYSA-N C1(=CC=CC=C1)C1N=C(C2=CC(=C(C=C12)Cl)Cl)OCC Chemical compound C1(=CC=CC=C1)C1N=C(C2=CC(=C(C=C12)Cl)Cl)OCC RTQCEQASWIGHNC-UHFFFAOYSA-N 0.000 description 1
- RHKUPVNCSBEIQD-UHFFFAOYSA-N C1(=CC=CC=C1)C1N=C(C2=CC=C(C=C12)Cl)OCC Chemical compound C1(=CC=CC=C1)C1N=C(C2=CC=C(C=C12)Cl)OCC RHKUPVNCSBEIQD-UHFFFAOYSA-N 0.000 description 1
- LRRIIRITNWWQEG-UHFFFAOYSA-N C1(=CC=CC=C1)C1N=C(C2=CC=C(C=C12)F)OCC Chemical compound C1(=CC=CC=C1)C1N=C(C2=CC=C(C=C12)F)OCC LRRIIRITNWWQEG-UHFFFAOYSA-N 0.000 description 1
- LEPLEKYZWDTGCU-UHFFFAOYSA-N C1(=CC=CC=C1)C1N=C(C2=CC=CC(=C12)Cl)OCC Chemical compound C1(=CC=CC=C1)C1N=C(C2=CC=CC(=C12)Cl)OCC LEPLEKYZWDTGCU-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- XXKDVASBGXAMPL-UHFFFAOYSA-N ClC=1C=C(C=C(C1)Cl)C1N=C(C2=CC=CC=C12)OCC Chemical compound ClC=1C=C(C=C(C1)Cl)C1N=C(C2=CC=CC=C12)OCC XXKDVASBGXAMPL-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000006711 Pistacia vera Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1479043A SU379090A3 (https=) | 1968-06-19 | 1969-06-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73812168A | 1968-06-19 | 1968-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU414790A3 true SU414790A3 (ru) | 1974-02-05 |
Family
ID=24966662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1338547A SU414790A3 (ru) | 1968-06-19 | 1969-06-17 | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2,3-ДИГИДРО-5Н-ИМИДАЗО[2,1-о]ИЗОИНДОЛА12 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3597445A (https=) |
| JP (2) | JPS4843758B1 (https=) |
| AT (2) | AT303718B (https=) |
| BE (1) | BE734704A (https=) |
| BR (1) | BR6909879D0 (https=) |
| CH (1) | CH513895A (https=) |
| CS (2) | CS161087B2 (https=) |
| DE (2) | DE1950842A1 (https=) |
| FR (1) | FR2011200A1 (https=) |
| GB (1) | GB1257264A (https=) |
| HU (1) | HU165996B (https=) |
| NL (1) | NL6909361A (https=) |
| PL (1) | PL80120B1 (https=) |
| SE (2) | SE370236B (https=) |
| SU (1) | SU414790A3 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905994A (en) * | 1967-03-30 | 1975-09-16 | Hoffmann La Roche | 2-{8 2-(1,3-DIAZACYCLOALK-2-ENYL{9 BENZOPHENONE DERIVATIVES AND 1,3-DIAZACYCLOALKENYL{8 2,1-A{9 isoindole derivatives |
| US4210585A (en) * | 1978-05-22 | 1980-07-01 | Sandoz, Inc. | Process for preparing 9H-dibenz[c,f]imidazo[1,2-a][1]azepin-9-ones |
| JP2013523757A (ja) * | 2010-03-31 | 2013-06-17 | スパーナス ファーマシューティカルズ インコーポレイテッド | マジンドールの製剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH500198A (de) * | 1967-03-23 | 1970-12-15 | Sandoz Ag | Verfahren zur Herstellung von 5-Hydroxy-5-phenyl-2,3-dihydro-5H-imidazo(2,1-a)isoindolen |
-
1968
- 1968-06-19 US US738121A patent/US3597445A/en not_active Expired - Lifetime
-
1969
- 1969-05-20 CH CH765469A patent/CH513895A/de not_active IP Right Cessation
- 1969-05-22 GB GB1257264D patent/GB1257264A/en not_active Expired
- 1969-05-30 SE SE7213158A patent/SE370236B/xx unknown
- 1969-05-30 SE SE07654/69*A patent/SE354073B/xx unknown
- 1969-06-16 DE DE19691950842 patent/DE1950842A1/de active Pending
- 1969-06-16 DE DE19691930488 patent/DE1930488A1/de active Pending
- 1969-06-17 CS CS193*[A patent/CS161087B2/cs unknown
- 1969-06-17 AT AT573269A patent/AT303718B/de not_active IP Right Cessation
- 1969-06-17 CS CS4275A patent/CS161086B2/cs unknown
- 1969-06-17 PL PL1969134250A patent/PL80120B1/pl unknown
- 1969-06-17 FR FR6920111A patent/FR2011200A1/fr not_active Withdrawn
- 1969-06-17 AT AT203171A patent/AT306712B/de not_active IP Right Cessation
- 1969-06-17 BE BE734704D patent/BE734704A/xx unknown
- 1969-06-17 JP JP44047363A patent/JPS4843758B1/ja active Pending
- 1969-06-17 HU HUSA2046A patent/HU165996B/hu unknown
- 1969-06-17 SU SU1338547A patent/SU414790A3/ru active
- 1969-06-18 BR BR209879/69A patent/BR6909879D0/pt unknown
- 1969-06-19 NL NL6909361A patent/NL6909361A/xx unknown
-
1973
- 1973-01-11 JP JP48005581A patent/JPS4921135B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1930488A1 (de) | 1970-03-19 |
| BR6909879D0 (pt) | 1973-01-09 |
| BE734704A (https=) | 1969-12-17 |
| JPS4921135B1 (https=) | 1974-05-30 |
| HU165996B (https=) | 1974-12-28 |
| CH513895A (de) | 1971-10-15 |
| CS161086B2 (https=) | 1975-05-04 |
| NL6909361A (https=) | 1969-12-23 |
| FR2011200A1 (https=) | 1970-02-27 |
| CS161087B2 (https=) | 1975-05-04 |
| JPS4843758B1 (https=) | 1973-12-20 |
| AT306712B (de) | 1973-04-25 |
| US3597445A (en) | 1971-08-03 |
| SE370236B (https=) | 1974-10-07 |
| DE1950842A1 (de) | 1970-05-06 |
| GB1257264A (https=) | 1971-12-15 |
| AT303718B (de) | 1972-12-11 |
| PL80120B1 (https=) | 1975-08-30 |
| SE354073B (https=) | 1973-02-26 |
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