IL28825A - 9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-(4)-one - Google Patents
9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-(4)-oneInfo
- Publication number
- IL28825A IL28825A IL2882564A IL2882564A IL28825A IL 28825 A IL28825 A IL 28825A IL 2882564 A IL2882564 A IL 2882564A IL 2882564 A IL2882564 A IL 2882564A IL 28825 A IL28825 A IL 28825A
- Authority
- IL
- Israel
- Prior art keywords
- benzo
- acid
- july
- production
- cyclohepta
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims 3
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000001117 sulphuric acid Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/30—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/26—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
The present invention relates to a new thiophene derivative and to a process for its new thiophene derivative of the invention is has the formula This can serve as a starting material for the production of pharmaceutically active those described in Israel fatent Specification which compounds have the formulae prepared via the compounds in which and are hydrogen or lower radicals and are lower alkyl radicals or together a t methylene or pentamethylene the proviso that when is may form together with a or and when is may form together a dimethylene or trimethylene The invention also consists in a process for the preparation of the above acid is reduced to acid which latter is subjected to intramolecular ring Sodium amalgam in an a alcohol for example be used as reducing The ring closure is effected in the presence of a condensation agent such as sulfuric acid or a hosphoric the ring closure is effected by heating the acid with phosphoric acid into which phosphorus pentoxide has been The thie acid can be prepared in that is condensed with acid in an anhydrous solvent and in the presence of an alkaline condensation The invention is illustrated by the following Example g of chloride ram are o of heated to then phosphite is slowly added with stirring at the same and the mixture is heated for a further two hours at with The reaction mixture then distilled in a high phosphonate distils at mm acid 30 g of well dried sodium h e are added to a of g of phonate in 200 cc of freshly distilled dimethyl in a The temperature of the solution rises to in the course of the dissolving The flask is then placed in an ice bath a solution of 80 g of acid in 200 cc of dimethyl formamide is added dropwise with stirring at such a rate that the temperature remains between 35 and 40 and the stirring is then continued minutes at room 1600 cc of water are then added to the reaction solution whilst the latter is cooled a red oil The material is then made alkaline with potassium upon the oil the solution is extracted three times with benzene and the aqueous phase is carefully adjusted to a value of 4 at with hydrochloric The mixture is left to stand for several hours in a then the precipitated acid is filtered dried and from Its melting point is then The mother liquor is extracted three times with methylene the organic phase is dried over sodium sulphate and evaporated at 15 The residue is crystallized from whereby a further portion of the above acid is g of sodium are melted anhydrous thereafter 375 g of pure mercury added dropwise whilst the mixture is shaken at frequent By the developing heat the toluene is made to The mixture is then heated o to C with and as soon as the toluene has tilled is cooled to a temperature of The homogeneous amalgam is then covered with a solution of 20 g of acid in 150 cc of ethanol and the mixture is shaken for The mercury is then separated and washed twice with and the combined ethanolic solutions are diluted with 00 cc of The solution is filtered through highly purified diatomaceous acidified with hydrochloric acid and cooled to After acid is filtered off recrystallized from Melting point 59 cc of 8 phosphoric acid and 86 g of phosphorus pentoxide are stirred for 30 at then 20 g of powdered acid are introduced in the course of minutes at this The reaction mixture is stirred for a further two hours at 1 then poured into cc of the solution is filtered through highly purified diatomaceous earth and extracted three times methylene The organic phase is washed with 2 aqueous sodium dried over magnesium the methylene chloride is removed by evaporation and the residue ia distilled in a high The product is which distils as a green oil at insufficientOCRQuality
Claims (1)
- particularly described and ascertained the nature of our said invention and in what the same is to he we declare that what we claim 4 28th July A process for the production of benzo which comprises subjecting to molecular ring 28th A process according to Glaim wherein the ring closure is effected with aid of a condensation A process according to wherein the condensatio agent is sulphuric acid or a polyphosphoric 28th A process for the production of benzo whieh comprises reducing acid to form aeid and subjecting the latter to intramolecular ring 29th July A process for the production of benzo substantially as herein described with reference the 29th July Dated this 24th day of For the Applicants insufficientOCRQuality
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH941863A CH435314A (en) | 1963-07-29 | 1963-07-29 | Process for the preparation of new heterocyclic compounds |
| CH1570763 | 1963-12-20 | ||
| CH1571163A CH437348A (en) | 1963-12-20 | 1963-12-20 | Process for the preparation of new heterocyclic compounds |
| CH669964 | 1964-05-22 | ||
| CH685864 | 1964-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28825A true IL28825A (en) | 1968-09-26 |
Family
ID=27509281
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2882564A IL28825A (en) | 1963-07-29 | 1964-07-28 | 9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-(4)-one |
| IL2263964A IL22639A (en) | 1963-07-29 | 1964-12-18 | 4h-benzo(4,5)cyclohepta(1,2-b)thiophene derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2263964A IL22639A (en) | 1963-07-29 | 1964-12-18 | 4h-benzo(4,5)cyclohepta(1,2-b)thiophene derivatives |
Country Status (10)
| Country | Link |
|---|---|
| BE (2) | BE651101A (en) |
| BR (1) | BR6461194D0 (en) |
| DE (2) | DE1225660B (en) |
| FI (1) | FI42575B (en) |
| FR (2) | FR3778M (en) |
| GB (3) | GB1074745A (en) |
| IL (2) | IL28825A (en) |
| NL (2) | NL126889C (en) |
| NO (1) | NO115583B (en) |
| SE (1) | SE313819B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464983A (en) * | 1964-02-04 | 1969-09-02 | Sandoz Ag | 4h-benzo(4,5)cyclohepta(1,2-b)thiophenes |
| FR2344284A1 (en) | 1976-03-17 | 1977-10-14 | Cerm Cent Europ Rech Mauvernay | NEW TRICYCLIC COMPOUNDS WITH A FURANNIC CYCLE AND THEIR APPLICATION AS ANTIDEPRESSANTS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE616813A (en) * | 1961-04-26 | 1962-10-24 | Sandoz Sa | New heterocyclic compounds and their preparation |
-
1963
- 1963-07-24 GB GB5227465A patent/GB1074745A/en not_active Expired
-
1964
- 1964-07-24 NL NL6408529A patent/NL126889C/xx active
- 1964-07-24 GB GB29803/64A patent/GB1074744A/en not_active Expired
- 1964-07-25 DE DES92271A patent/DE1225660B/en active Pending
- 1964-07-28 FI FI161864A patent/FI42575B/fi active
- 1964-07-28 SE SE916364A patent/SE313819B/xx unknown
- 1964-07-28 BR BR16119464A patent/BR6461194D0/en unknown
- 1964-07-28 IL IL2882564A patent/IL28825A/en unknown
- 1964-07-28 BE BE651101A patent/BE651101A/xx unknown
- 1964-10-26 FR FR992654A patent/FR3778M/en not_active Expired
- 1964-12-11 GB GB5047564A patent/GB1084447A/en not_active Expired
- 1964-12-15 NL NL6414606A patent/NL6414606A/xx unknown
- 1964-12-16 DE DE1964S0094649 patent/DE1249879B/en active Pending
- 1964-12-18 BE BE657365A patent/BE657365A/xx unknown
- 1964-12-18 NO NO15605464A patent/NO115583B/no unknown
- 1964-12-18 IL IL2263964A patent/IL22639A/en unknown
-
1965
- 1965-03-17 FR FR9517A patent/FR4224M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BR6461194D0 (en) | 1973-08-09 |
| SE313819B (en) | 1969-08-25 |
| NL6408529A (en) | 1965-02-01 |
| BE657365A (en) | 1965-06-18 |
| DE1249879B (en) | 1967-09-14 |
| FR4224M (en) | 1966-06-13 |
| NL126889C (en) | 1969-02-17 |
| GB1084447A (en) | 1967-09-20 |
| FI42575B (en) | 1970-06-01 |
| IL22639A (en) | 1968-08-22 |
| NO115583B (en) | 1968-10-28 |
| FR3778M (en) | 1965-12-20 |
| NL6414606A (en) | 1965-06-21 |
| GB1074744A (en) | 1967-07-05 |
| DE1225660B (en) | 1966-09-29 |
| GB1074745A (en) | 1967-07-05 |
| BE651101A (en) | 1965-01-28 |
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