GB834336A - (4-biphenylyl-pyridyl)-carbinols - Google Patents
(4-biphenylyl-pyridyl)-carbinolsInfo
- Publication number
- GB834336A GB834336A GB2543057A GB2543057A GB834336A GB 834336 A GB834336 A GB 834336A GB 2543057 A GB2543057 A GB 2543057A GB 2543057 A GB2543057 A GB 2543057A GB 834336 A GB834336 A GB 834336A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromide
- phenyl
- acid
- pyridyl
- biphenylyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KGFYABZIGNOTGS-UHFFFAOYSA-N [4-(2-phenylphenyl)pyridin-2-yl]methanol Chemical class C1=NC(CO)=CC(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 KGFYABZIGNOTGS-UHFFFAOYSA-N 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- 238000003747 Grignard reaction Methods 0.000 abstract 2
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- VTZULUGFNSAEIC-UHFFFAOYSA-N bis[4-(2-phenylphenyl)pyridin-2-yl]methanone Chemical compound C1(=C(C=CC=C1)C1=CC(=NC=C1)C(=O)C1=NC=CC(=C1)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 VTZULUGFNSAEIC-UHFFFAOYSA-N 0.000 abstract 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000008196 pharmacological composition Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 abstract 1
- QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 abstract 1
- WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 abstract 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 abstract 1
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 abstract 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 abstract 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 229940125717 barbiturate Drugs 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- -1 cycloalkyl bromides Chemical class 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000004694 iodide salts Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 abstract 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises (4-biphenyl-pyridyl)-a -substituted carbinols of formula <FORM:0834336/IV (b)/1> in which X is a phenyl, substituted phenyl, alkyl, aralkyl or cycloalkyl radical. They may be prepared by reacting a 4-biphenylyl-pyridyl ketone with a Grignard reagent of the formula X-Mg-Y, in which Y is a halogen atom, in an organic solvent at elevated temperature and subjecting the resulting mixture to mild hydrolysis. The 4-biphenylyl-pyridyl ketones used as starting materials may be prepared by condensing isonicotinic acid chloride or nicotinic acid chloride, preferably in the presence of a condensing agent such as aluminium chloride, with diphenyl and hydrolysing the product. The condensation step is conveniently carried out in an organic solvent, e.g. carbon disulphide, at a temperature between 40 DEG and 150 DEG C. The ketones are converted as above to the carbinols using a Grignard reagent. Suitable halides for use in the Grignard reaction are, for example, phenyl bromide, m- and p-methyl phenyl bromide, p-methoxyphenyl bromide, o-, m- and p-chlorphenyl bromide, o-, m- and p-fluorophenyl bromide, dichlorophenyl bromide and lower alkyl and cycloalkyl bromides and iodides. Suitable solvents for the Grignard reaction are diethyl ether, tetrahydrofuran, benzene, toluene, xylene and anisole and the reaction is conveniently carried out at the boiling-point of the solvent, preferably between 30 DEG and 150 DEG C. The mild hydrolysis of the product may be carried out by an ammonium salt or by dilute acetic acid followed by dilute alkali. The compound may be isolated as the free base or as a crystalline salt by treating the free base with an acid such as hydrochloric acid. The products may be used in pharmacological compositions (see Group VI).ALSO:Pharmacological compositions comprise a drug active on the central nervous system as a stimulant or depressant, for example barbiturates, such as 5-(1-methylbutyl)-51-ethyl barbituric acid, 1.5 - dimethyl - 51 - cyclohexenyl barbituric acid and 2 - thio - 5 - ethyl-51 - (1 - methylbutyl) - barbituric acid, and a compound of general formula <FORM:0834336/VI/1> in which X is a phenyl, substituted phenyl, alkyl, aralkyl or cycloalkyl radical, used in an amount sufficient to potentiate the action of the drug.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2543057A GB834336A (en) | 1957-08-12 | 1957-08-12 | (4-biphenylyl-pyridyl)-carbinols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2543057A GB834336A (en) | 1957-08-12 | 1957-08-12 | (4-biphenylyl-pyridyl)-carbinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB834336A true GB834336A (en) | 1960-05-04 |
Family
ID=10227540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2543057A Expired GB834336A (en) | 1957-08-12 | 1957-08-12 | (4-biphenylyl-pyridyl)-carbinols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB834336A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106535635A (en) * | 2014-04-15 | 2017-03-22 | 美国陶氏益农公司 | Metalloenzyme inhibitor compounds as fungicides |
| CN116947610A (en) * | 2023-06-16 | 2023-10-27 | 中昊(大连)化工研究设计院有限公司 | New synthetic route for cyclobutanone |
-
1957
- 1957-08-12 GB GB2543057A patent/GB834336A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106535635A (en) * | 2014-04-15 | 2017-03-22 | 美国陶氏益农公司 | Metalloenzyme inhibitor compounds as fungicides |
| JP2017517493A (en) * | 2014-04-15 | 2017-06-29 | ダウ アグロサイエンシィズ エルエルシー | Metalloenzyme inhibitor compounds as fungicides |
| EP3131400A4 (en) * | 2014-04-15 | 2017-11-29 | Dow AgroSciences LLC | Metalloenzyme inhibitor compounds as fungicides |
| US9957252B2 (en) | 2014-04-15 | 2018-05-01 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| CN116947610A (en) * | 2023-06-16 | 2023-10-27 | 中昊(大连)化工研究设计院有限公司 | New synthetic route for cyclobutanone |
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