YU46093B - PROCEDURE FOR OBTAINING TRICYCLIC KETONE - Google Patents
PROCEDURE FOR OBTAINING TRICYCLIC KETONEInfo
- Publication number
- YU46093B YU46093B YU217487A YU217487A YU46093B YU 46093 B YU46093 B YU 46093B YU 217487 A YU217487 A YU 217487A YU 217487 A YU217487 A YU 217487A YU 46093 B YU46093 B YU 46093B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- compound
- group
- hydrogen atom
- solvent
- Prior art date
Links
Classifications
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
POSTUPAK ZA DOBIJANJE TRICIKLIČNIH KETONA, opšte formule: u kojoj Im predstavlja imidazolil grupu formule: R1 je atom vodonika ili C1-3-alkil; R2, R3 i R4 svaki nezavisno predstavljaju atom vodonika ili C1-3alkil; Q predstavlja atom vodonika ili halogen, kao što je fluor; n ima vrednost 2 ili 3; i A-B predstavlja grupu C=CH ili CH-CH2, ili njihovih fiziološki prihvatljivih soli, u svim izomernim oblicima uključujući i smeše izomera, naznačen time, što jedinjenje formule: u kojoj su R1, Q i n kao što je definisano ranije, reaguje sa jedinjenjem formule: OHC-Im u kojoj je Im kao što je definisano ranije, ili sa njegovim derivatom u kome je imidazolski azotov atom zaštićen arilmetil grupom, u inertnom rastvaraču kao što je etar, na primer tetrahidrofuran, na temperaturi od oko -80 do 30 C i u prisustvu baze kao što je amid alkalnog metala, na primer litijum diizopropilamid, da bi se dobilo jedinjenje formule: u kojoj su R1, Q, n i Im kao što je definisano ranije, ili njegov derivat u kome je imidazolski azotov atom zaštićen arilmetil grupom; što se jedinjenje formule (II) podvrgava dehidrataciji uz korišćenje organske kiseline kao što je sulfonska, na primer p-toluolsulfonska ili metansulfonska kiselina, u rastvaraču kao što je etar, na primer tetrahidrofuran, ili sirćetna kiselina, na temperaturi refluksa reakcione smeše, da bi se dobilo jedinjenje formule (I) u kojoj A-B predstavlja grupu C=CH; što se jedinjenje formule (I) u kojoj A-B predstavlja grupu C=CH, po potrebi, prevodi u jedinjenje formule (I) u kojoj A-B predstavlja grupu CH-CH2, hidrogenacijom u prisustvu katalizatora od plemenitog metala, kao što je paladijum, u rastvaraču kao što je alkohol, na primer metanol ili etanol i na temperaturi od 20 do 30° C; i što se dobijeni proizvod formule (I), po potrebi, prevodi u svoju fiziološki prihvatljivu so.A process for the preparation of tricyclic ketones of the general formula: wherein Im represents an imidazolyl group of the formula: R 1 is a hydrogen atom or C 1-3 alkyl; R 2, R 3 and R 4 each independently represent a hydrogen atom or C 1-3 alkyl; Q represents a hydrogen atom or halogen, such as fluorine; n has a value of 2 or 3; and AB represents a group C = CH or CH-CH2, or physiologically acceptable salts thereof, in all isomeric forms including mixtures of isomers, wherein the compound of formula: wherein R 1, Q in as defined above reacts with the compound of formula: OHC-Im in which Im is as previously defined, or with a derivative thereof in which the imidazole nitrogen atom is protected by an arylmethyl group, in an inert solvent such as ether, for example tetrahydrofuran, at a temperature of about -80 to 30 C and in the presence of a base such as an alkali metal amide, for example lithium diisopropylamide, to give a compound of formula: wherein R 1, Q, or Im are as previously defined, or a derivative thereof wherein the imidazole nitrogen atom is protected by an arylmethyl group; that the compound of formula (II) is subjected to dehydration using an organic acid such as a sulfonic acid, for example p-toluenesulfonic or methanesulfonic acid, in a solvent such as ether, for example tetrahydrofuran, or acetic acid, at the reflux temperature of the reaction mixture, in order to a compound of formula (I) is obtained in which AB represents a group C = CH; wherein the compound of formula (I) in which AB represents a C = CH group is, if necessary, converted into a compound of formula (I) in which AB represents a CH-CH2 group, by hydrogenation in the presence of a noble metal catalyst such as palladium in a solvent such as alcohol, for example methanol or ethanol and at a temperature of 20 to 30 ° C; and that the resulting product of formula (I), if necessary, is converted into its physiologically acceptable salt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868628473A GB8628473D0 (en) | 1986-11-28 | 1986-11-28 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU217487A YU217487A (en) | 1989-08-31 |
| YU46093B true YU46093B (en) | 1992-12-21 |
Family
ID=10608104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU217487A YU46093B (en) | 1986-11-28 | 1987-12-02 | PROCEDURE FOR OBTAINING TRICYCLIC KETONE |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS63211279A (en) |
| KR (1) | KR960009433B1 (en) |
| CN (1) | CN1020101C (en) |
| EG (1) | EG18509A (en) |
| GB (1) | GB8628473D0 (en) |
| HU (1) | HU199142B (en) |
| IS (1) | IS1456B6 (en) |
| MX (1) | MX9517A (en) |
| MY (1) | MY102646A (en) |
| PL (1) | PL158340B1 (en) |
| PT (1) | PT86230B (en) |
| SU (1) | SU1731047A3 (en) |
| UA (1) | UA19161A (en) |
| YU (1) | YU46093B (en) |
| ZA (1) | ZA878923B (en) |
| ZW (1) | ZW22587A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2106642C (en) * | 1992-10-14 | 2005-08-16 | Peter Bod | Carbazolone derivatives and process for preparing the same |
| CN103864762B (en) * | 2014-03-13 | 2016-07-06 | 天津师范大学 | Double; two (pyridin-4-yl acetenyl) carbazole derivates of 3,6-and its preparation method and application |
| CN104119320B (en) * | 2014-07-10 | 2016-10-05 | 中国科学院理化技术研究所 | A kind of application of pyridine-4-acetenyl carbazole organic salt derivant |
-
1986
- 1986-11-28 GB GB868628473A patent/GB8628473D0/en active Pending
-
1987
- 1987-11-26 MY MYPI87003114A patent/MY102646A/en unknown
- 1987-11-26 CN CN87107308A patent/CN1020101C/en not_active Expired - Fee Related
- 1987-11-27 ZW ZW225/87A patent/ZW22587A1/en unknown
- 1987-11-27 SU SU874203791A patent/SU1731047A3/en active
- 1987-11-27 IS IS3289A patent/IS1456B6/en unknown
- 1987-11-27 UA UA4203791A patent/UA19161A/en unknown
- 1987-11-27 JP JP62299652A patent/JPS63211279A/en active Pending
- 1987-11-27 MX MX951787A patent/MX9517A/en unknown
- 1987-11-27 ZA ZA878923A patent/ZA878923B/en unknown
- 1987-11-27 PL PL1987269095A patent/PL158340B1/en unknown
- 1987-11-27 HU HU875350A patent/HU199142B/en not_active IP Right Cessation
- 1987-11-27 PT PT86230A patent/PT86230B/en not_active IP Right Cessation
- 1987-11-27 KR KR1019870013420A patent/KR960009433B1/en not_active IP Right Cessation
- 1987-11-29 EG EG69587A patent/EG18509A/en active
- 1987-12-02 YU YU217487A patent/YU46093B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EG18509A (en) | 1994-02-28 |
| GB8628473D0 (en) | 1987-01-07 |
| KR960009433B1 (en) | 1996-07-19 |
| PL269095A1 (en) | 1988-09-01 |
| YU217487A (en) | 1989-08-31 |
| ZA878923B (en) | 1988-10-26 |
| CN1020101C (en) | 1993-03-17 |
| MY102646A (en) | 1992-08-17 |
| IS1456B6 (en) | 1991-01-16 |
| PT86230B (en) | 1990-11-07 |
| KR880006232A (en) | 1988-07-22 |
| HU199142B (en) | 1990-01-29 |
| JPS63211279A (en) | 1988-09-02 |
| PT86230A (en) | 1987-12-01 |
| UA19161A (en) | 1997-12-25 |
| SU1731047A3 (en) | 1992-04-30 |
| IS3289A7 (en) | 1988-05-29 |
| HUT45993A (en) | 1988-09-28 |
| CN87107308A (en) | 1988-06-08 |
| ZW22587A1 (en) | 1988-10-19 |
| MX9517A (en) | 1993-11-01 |
| PL158340B1 (en) | 1992-08-31 |
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