HU182477B - Process for transforming 10,11-epoxy-10,11-dihydro-5h-dibenzo-square bracket-b,f-square bracket closed-azepine -5-carboxamide for producing 10-oxo-10,11-dihydro-5h-dibenz-square bracket-b,f-square bracket closed-azepine-5-carboxamide - Google Patents
Process for transforming 10,11-epoxy-10,11-dihydro-5h-dibenzo-square bracket-b,f-square bracket closed-azepine -5-carboxamide for producing 10-oxo-10,11-dihydro-5h-dibenz-square bracket-b,f-square bracket closed-azepine-5-carboxamide Download PDFInfo
- Publication number
- HU182477B HU182477B HU79CI1926A HUCI001926A HU182477B HU 182477 B HU182477 B HU 182477B HU 79CI1926 A HU79CI1926 A HU 79CI1926A HU CI001926 A HUCI001926 A HU CI001926A HU 182477 B HU182477 B HU 182477B
- Authority
- HU
- Hungary
- Prior art keywords
- azepine
- carboxamide
- dihydro
- square bracket
- dibenz
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 18
- 230000001131 transforming effect Effects 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011777 magnesium Substances 0.000 claims abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Inorganic materials [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- ZRWWEEVEIOGMMT-UHFFFAOYSA-N carbamazepine-10,11-epoxide Chemical compound NC(=O)N1C2=CC=CC=C2C2OC2C2=CC=CC=C12 ZRWWEEVEIOGMMT-UHFFFAOYSA-N 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical group CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910001622 calcium bromide Inorganic materials 0.000 claims 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims 1
- 229940046413 calcium iodide Drugs 0.000 claims 1
- 229910001623 magnesium bromide Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- ZFXVFMBOFIEPII-UHFFFAOYSA-N 1h-azepine-4-carboxamide Chemical compound NC(=O)C1=CC=CNC=C1 ZFXVFMBOFIEPII-UHFFFAOYSA-N 0.000 abstract description 5
- 150000004677 hydrates Chemical class 0.000 abstract description 4
- 230000008707 rearrangement Effects 0.000 abstract description 4
- 239000011575 calcium Substances 0.000 abstract description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052791 calcium Inorganic materials 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 229910052749 magnesium Inorganic materials 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000001035 drying Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 3
- 229910001641 magnesium iodide Inorganic materials 0.000 description 3
- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 2
- FIEKVYPYFQSFTP-UHFFFAOYSA-N 6-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C FIEKVYPYFQSFTP-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic epoxides Chemical class 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical class C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WNEUNPWLVWPBGB-UHFFFAOYSA-N 1,6-dimethyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2(C)OC21C WNEUNPWLVWPBGB-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- MIOWCLFTUUSRGK-UHFFFAOYSA-N bicyclo[4.1.0]heptane-7-carbaldehyde Chemical compound C1CCCC2C(C=O)C21 MIOWCLFTUUSRGK-UHFFFAOYSA-N 0.000 description 1
- WUSJALRVWRGZMI-UHFFFAOYSA-L calcium;diiodide;tetrahydrate Chemical compound O.O.O.O.[Ca+2].[I-].[I-] WUSJALRVWRGZMI-UHFFFAOYSA-L 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH413478A CH633271A5 (en) | 1978-04-18 | 1978-04-18 | Process for the rearrangement of 10,11-epoxy-10,11-dihydro-5H-dibenz[b,f]azepines to give 10-oxo-10,11-dihydro-5H-dibenz(b,f)azepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182477B true HU182477B (en) | 1984-01-30 |
Family
ID=4270467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79CI1926A HU182477B (en) | 1978-04-18 | 1979-04-17 | Process for transforming 10,11-epoxy-10,11-dihydro-5h-dibenzo-square bracket-b,f-square bracket closed-azepine -5-carboxamide for producing 10-oxo-10,11-dihydro-5h-dibenz-square bracket-b,f-square bracket closed-azepine-5-carboxamide |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS54138588A (es) |
| AR (1) | AR222329A1 (es) |
| AT (1) | AT373877B (es) |
| BG (1) | BG29282A3 (es) |
| CA (1) | CA1112241A (es) |
| CH (1) | CH633271A5 (es) |
| DK (1) | DK157779A (es) |
| ES (1) | ES479600A1 (es) |
| FI (1) | FI70010C (es) |
| GR (1) | GR72260B (es) |
| HU (1) | HU182477B (es) |
| NL (1) | NL7902811A (es) |
| NO (1) | NO149776C (es) |
| PL (1) | PL214954A1 (es) |
| PT (1) | PT69495A (es) |
| SE (1) | SE7903328L (es) |
| YU (1) | YU91779A (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0112812D0 (en) | 2001-05-25 | 2001-07-18 | Portela & Ca Sa | Mthd for preparation of 10, 11-dihydro-10-hydroxy-5H-dibenz/B,F/azepine-5-c arboxamide and 10,11-dihydro-10-oxo-5H-dibenz/B,F/azepine-5-carb oxamide therefrom |
| CA2471666C (en) | 2004-06-18 | 2009-10-13 | Apotex Pharmachem Inc. | An improved process for the preparation of oxcarbazepine and related intermediates |
| GB2422149A (en) | 2005-01-14 | 2006-07-19 | Portela & Ca Sa | Process for the preparation of 10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide |
-
1978
- 1978-04-18 CH CH413478A patent/CH633271A5/de not_active IP Right Cessation
-
1979
- 1979-04-07 GR GR58835A patent/GR72260B/el unknown
- 1979-04-10 NL NL7902811A patent/NL7902811A/xx not_active Application Discontinuation
- 1979-04-12 CA CA325,802A patent/CA1112241A/en not_active Expired
- 1979-04-16 ES ES479600A patent/ES479600A1/es not_active Expired
- 1979-04-16 BG BG043253A patent/BG29282A3/xx unknown
- 1979-04-16 AR AR276195A patent/AR222329A1/es active
- 1979-04-17 AT AT0288379A patent/AT373877B/de not_active IP Right Cessation
- 1979-04-17 PL PL21495479A patent/PL214954A1/xx unknown
- 1979-04-17 HU HU79CI1926A patent/HU182477B/hu unknown
- 1979-04-17 FI FI791233A patent/FI70010C/fi not_active IP Right Cessation
- 1979-04-17 YU YU00917/79A patent/YU91779A/xx unknown
- 1979-04-17 NO NO791274A patent/NO149776C/no unknown
- 1979-04-17 PT PT69495A patent/PT69495A/pt unknown
- 1979-04-17 DK DK157779A patent/DK157779A/da not_active IP Right Cessation
- 1979-04-17 SE SE7903328A patent/SE7903328L/xx not_active Application Discontinuation
- 1979-04-18 JP JP4680279A patent/JPS54138588A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO791274L (no) | 1979-10-19 |
| FI791233A (fi) | 1979-10-19 |
| YU91779A (en) | 1983-01-21 |
| CH633271A5 (en) | 1982-11-30 |
| ES479600A1 (es) | 1979-07-16 |
| FI70010B (fi) | 1986-01-31 |
| NO149776C (no) | 1984-06-20 |
| SE7903328L (sv) | 1979-10-19 |
| FI70010C (fi) | 1986-09-12 |
| NO149776B (no) | 1984-03-12 |
| JPS54138588A (en) | 1979-10-27 |
| BG29282A3 (en) | 1980-10-15 |
| AR222329A1 (es) | 1981-05-15 |
| NL7902811A (nl) | 1979-10-22 |
| CA1112241A (en) | 1981-11-10 |
| AT373877B (de) | 1984-02-27 |
| DK157779A (da) | 1979-10-19 |
| PL214954A1 (es) | 1980-07-01 |
| PT69495A (en) | 1979-05-01 |
| ATA288379A (de) | 1983-07-15 |
| GR72260B (es) | 1983-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Stork et al. | The SN2'Reaction. III. Structure and SN2'Reactions of the Halocodides | |
| Bender et al. | Periodate oxidation of. alpha.-keto. gamma.-lactams. Enol oxidation and. beta.-lactam formation. Mechanism of periodate hydroxylation reactions | |
| Fiego et al. | Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation | |
| HU182477B (en) | Process for transforming 10,11-epoxy-10,11-dihydro-5h-dibenzo-square bracket-b,f-square bracket closed-azepine -5-carboxamide for producing 10-oxo-10,11-dihydro-5h-dibenz-square bracket-b,f-square bracket closed-azepine-5-carboxamide | |
| Ackrell et al. | Furazans and furazan oxides. Part I. Synthesis and reactions of some strained furazan N-oxides | |
| KR101098201B1 (ko) | 불소화된 펜타센 유도체 및 그들의 제조방법 | |
| Eck et al. | The Preparation of 3, 5-and 4, 6-Cholestadienes and a Study of Cholesterilene and of “7-Dehydrocholestene Isomer” | |
| Waali et al. | 4, 5-Benzo-1, 2, 4, 6-cycloheptatetraene | |
| Quin et al. | 1-Phenyl-cis-3a, 7a-dihydrophosphindole and its properties | |
| HU178581B (en) | Process for producing 6-chloro-alpha-methyl-carbasole-2-acetic acid | |
| US3383420A (en) | 5-(gamma-hydroxypropyl)-5h-dibenzo [a, d] cycloheptenes | |
| SU728718A3 (ru) | Способ получени триазоло-тиено- диазепин-1-онов | |
| JPS585902B2 (ja) | β↓−ニトロスチレン誘導体 | |
| Shirinyan et al. | Photochromic Dihetarylethenes. 8. A Novel Route to the Synthesis of 3, 4-Bis (2, 5-dimethyl-3-thienyl) furan-2, 5-dione as a Potential Photochrome | |
| HU190224B (en) | Process for producing methyl-2-tetradecyl-glycidate | |
| US3446821A (en) | Intermediates useful in preparation of butenolides and process therefor | |
| KR920702671A (ko) | 케톤화합물의 개량된 제조방법 | |
| JP3278957B2 (ja) | ３ーアリルフェノール類の製造法 | |
| Rodriguez et al. | Structural study of the methylnaphthazarins. X-ray structure of the tetramethylnaphthazarin, a charge transfer complex. | |
| AU607565B2 (en) | Improvement in the synthesis of 6-methylene derivatives of androsta-1, 4-diene-3,17-dione | |
| JP3012933B1 (ja) | ジチアナフタレノファン化合物とその製造方法 | |
| JPH11100376A (ja) | ２，３−ジヒドロベンゾ（ｂ）フラン誘導体および医薬品の製造方法 | |
| KR930003756B1 (ko) | 치환된 β-페닐아크릴산의 제조방법 | |
| Smith et al. | Methyl substituent effects on electrophilic additions to some benzobicyclooctadienes | |
| JPH0219117B2 (es) |