IL45113A - 6-substituted-2-benzoxyzolinone derivatives and their preparation - Google Patents
6-substituted-2-benzoxyzolinone derivatives and their preparationInfo
- Publication number
- IL45113A IL45113A IL45113A IL4511374A IL45113A IL 45113 A IL45113 A IL 45113A IL 45113 A IL45113 A IL 45113A IL 4511374 A IL4511374 A IL 4511374A IL 45113 A IL45113 A IL 45113A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- formula
- oxo
- compound
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- -1 oxo Compound Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229960004011 methenamine Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
derivatives and their preparation IHSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE The inventors Charles LESPAGNOL Daniel BONTE 43204 This invention relates to atives and their According to the present invention there are provided compounds of formula in which represents a hydrogen an unsubstituted or halogen substituted alkyl group containing 1 to 6 carbon atoms or a phenyl or a benzyl or a thienyl R2 represents a hydrogen or an alkyl group ing 1 to 6 carbon and X represents a hydrogen atom and represents a hydroxy group or X and Y together represent an oxo Preferred conpounds are those wherein is as defined for I represents a hydrogen atom or a group and X and Y together represent an oxo According to another preferred grouping represents a hydrogen is as defined for formula I and X and Y together represent an oxo Of particular interest are those of formula I in wh ch represents a hydrogen atom or a chl benzyl or thienyl and represents a hydrogen or a The compounds of formula I may be prepared by reacting the presence of polyphosphoric of formula R is as defined with an acid of the formula is as defined or a functional deriva anhydride or to form a compound of formula I wherein X and Y together an oxo group if a of formula I wherein X represents a hydrogen atom and represents a hydroxy group is selectively reducing the said oxo group to the corresponding To prepare a compound of formula I wherein represents a hydrogen the compound of II is formylated with the aid of hexamethylene tetramine in the presence of the polyphosphoric This produces a compound of formula I which carries a group in the represents a hydrogen atom and X and Y represent n oxygen This be reduced to the corresponding alcohol if of the of in the present preparative process has been found in the presence of polyphosphoric Use of ional Crafts catalysts generally results in a total absence of reaction or in extremely The polyphospboric acid acts both as catalyst and solvent for the present The reduction of of I wherein X and Y together represent an oxo group of course be carried out without reduction of the keto group of the one This can be carried out in known for with the aid of sodium The of I are valuable in the chemical particularly in pharmaceutical for the preparation of compounds are difficult to prepare by conventional For example the compounds of the invention may be used to prepare nones with other substituents in the in particular benzoxaaolinones In addition the of I X and Y together represent an oxo group may by alkaline hydrolysis be converted to which themselves are useful These are described in our French Patent Publication The invention is further illustrated in the following EXAMPLE 1 0 g Acetic acid are added slowly and with stirring to a solution of g benzoxazolinone in polyphosphoric acid The mixture is progressively heated to and kept at this temperature for 2 After the reaction mixture is poured into iced water and stirred The precipitate obtained is extracted and recrystallised from ethyl alcohol Melting EXAMPLE 5 31 0 obtained according to Example 1 are dissolved in 50 ml of a 3 aqueous sodium hydroxide There is added slowly and with stirring 60 g 015 of sodium Stirring is continued for 3 hours and on the mixture is acidified with hydrochloric The precipitate formed extracted and recrystallised from Melting EXAMPLE 3 g 0 Hexamethylenetetramine are added to a solution of g 0 linone in 100 g polyphosphoric The mixture is heated to and stirred for 10 at this It is cooled rapidly and the reaction mixture poured into iced water with vigorous The precipitate obtained is washed with water and The mother liquors are treated several times with The combined ethereal solutions are washed with dried over sodium sulphate and the ether is evaporated A second fraction of the product is thus recovered and this combined with the Recrystallisation from ethyl alcohol is carried to Melting In the following Table compounds according to the invention are Compounds 1 to 12 were prepared by the method of Example compounds 13 to 16 by the method of Example 2 and compounds 17 and l8 by the method of Example Compound X Y Melting Point ion solvent 1 1 0 H 228 Alcohol 2 0 H 205 Alcohol 3 0 H Benzene 0 H 17 Benzene 5 0 II Alcohol 6 0 H 253 Alcohol 95 0 Alcohol 8 0 Alcohol 95 9 0 Alcohol 95 10 0 Benzene 11 0 179 Alcohol 95 12 0 158 Alcohol TABLE Compound X Y Rl Melting Recrystall Point ion solvent 13 K OK H Water H OH H 156 Wa er 15 H OH H 159 Alcohol 16 H OH H 179 Alcohol 17 3 0 H Alcohol 95 18 0 H H 190 Water insufficientOCRQuality
Claims (1)
1. CLAIMS in wh represents a hydrogen an unsubstituted Rl or halogen substituted alkyl group containing 1 to 6 carbon atoms or a phenyl or a benzyl or a thienyl represents a hydrogen atom or an alkyl group aining 1 to carbon and represents a hydrogen and Y represents a hydroxy or and Y together represent an oxo Compound according to 1 in which represents a hydrogen or a methyl group Y together represent an oxo according to 1 in which represents a hydrogen and and represent an oxo Co pound according claim 1 in which represents a chloro eth benzyl or thienyl and represents a hydrogen or methyl Any one of the numbered 2 to to 16 and 18 specifically identified Process for preparing a according to any one of the preceding which process reacting in the presence of polyphosphoric acid a of the is as defined in claim with an acid of formula is as defined in claim or a functional derivative thereof to forra compound of formula I wherein X and Y together represent an oxo group if of fornula I wherein X represents hydrogen atom and Y represents a hydroxy group is selectively reducing the said oxo group to the corresponding Process according to claim to prepare a compound wherein represents a hydrogen wherein the compound of formula II is the aid of te Process for preparing a of formula X as defined in 1 substantially as described reference to any oae of the Compounds of formula as defined in claim 1 whenever by the process in any one of f to insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7323280A FR2244506B1 (en) | 1973-06-26 | 1973-06-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45113A0 IL45113A0 (en) | 1974-09-10 |
| IL45113A true IL45113A (en) | 1977-06-30 |
Family
ID=9121568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45113A IL45113A (en) | 1973-06-26 | 1974-06-25 | 6-substituted-2-benzoxyzolinone derivatives and their preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5922711B2 (en) |
| BE (1) | BE816820A (en) |
| CA (1) | CA1019749A (en) |
| CH (2) | CH592642A5 (en) |
| DE (1) | DE2429562A1 (en) |
| DK (1) | DK341274A (en) |
| FR (1) | FR2244506B1 (en) |
| GB (1) | GB1425429A (en) |
| IL (1) | IL45113A (en) |
| LU (1) | LU70403A1 (en) |
| NL (1) | NL179135C (en) |
| NO (1) | NO143531C (en) |
| SE (1) | SE424865B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039929A1 (en) * | 1980-10-23 | 1982-06-03 | Bayer Ag, 5090 Leverkusen | ISOCYANATO-OXAZOLINONE, A METHOD FOR THE PRODUCTION OF PLASTIC PRECOWERS HAVING OXAZOLIN-2-ONE RINGS AND THE USE THEREOF FOR THE PRODUCTION OF HIGH-MOLECULAR PLASTICS |
| DE3042481A1 (en) * | 1980-11-11 | 1982-06-16 | A. Nattermann & Cie GmbH, 5000 Köln | (OMEGA) - (2-OXO-BENZAZOLINYL) -ALKANIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM |
| GB8325370D0 (en) * | 1983-09-22 | 1983-10-26 | Fujisawa Pharmaceutical Co | Benzoxazoline and benzothiazoline derivatives |
| FR2645149A1 (en) * | 1989-03-30 | 1990-10-05 | Adir | |
| US5166353A (en) * | 1989-04-28 | 1992-11-24 | Adir Et Compagnie | Benzothiazolinone compounds |
| FR2646350B1 (en) * | 1989-04-28 | 1991-06-28 | Adir | NOVEL BENZOTHIAZOLINON DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2663633B1 (en) * | 1990-06-22 | 1994-06-17 | Adir | NEW CHALCONES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2663634B1 (en) * | 1990-06-22 | 1992-09-04 | Adir | NOVEL ACYL BENZOXAZOLINONES, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2756825B1 (en) * | 1996-12-10 | 1999-01-08 | Adir | NOVEL [3H] -BENZOXAZOLE-2-THIONES AND [3H] - BENZOTHIAZOLE-2-THIONES DERIVATIVES, THEIR PREPARATION METHOD AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| RU2227458C2 (en) * | 1998-06-18 | 2004-04-27 | Новартис Аг | Application of benzasol compounds as repellent, composition containing these compounds and method for obtaining the composition |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| EA201170349A1 (en) * | 2008-08-18 | 2011-08-30 | Йейл Юниверсити | MIF MODULATORS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050526A (en) * | 1960-08-08 | 1962-08-21 | Rohm & Haas | 3-thiocyanomethyl-2-benzothiazolinones and benzoxazolinones |
-
1973
- 1973-06-26 FR FR7323280A patent/FR2244506B1/fr not_active Expired
-
1974
- 1974-06-20 DE DE2429562A patent/DE2429562A1/en not_active Withdrawn
- 1974-06-24 NL NLAANVRAGE7408489,A patent/NL179135C/en not_active IP Right Cessation
- 1974-06-24 GB GB2795274A patent/GB1425429A/en not_active Expired
- 1974-06-24 SE SE7408255A patent/SE424865B/en not_active IP Right Cessation
- 1974-06-25 NO NO742310A patent/NO143531C/en unknown
- 1974-06-25 IL IL45113A patent/IL45113A/en unknown
- 1974-06-25 DK DK341274A patent/DK341274A/da not_active Application Discontinuation
- 1974-06-25 CH CH372074A patent/CH592642A5/xx not_active IP Right Cessation
- 1974-06-25 CA CA203,335A patent/CA1019749A/en not_active Expired
- 1974-06-25 CH CH180477A patent/CH602679A5/xx not_active IP Right Cessation
- 1974-06-25 BE BE145848A patent/BE816820A/en not_active IP Right Cessation
- 1974-06-25 LU LU70403A patent/LU70403A1/xx unknown
- 1974-06-26 JP JP49073743A patent/JPS5922711B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH602679A5 (en) | 1978-07-31 |
| NO143531B (en) | 1980-11-24 |
| BE816820A (en) | 1974-12-27 |
| JPS5069073A (en) | 1975-06-09 |
| NL179135C (en) | 1986-07-16 |
| SE7408255L (en) | 1974-12-27 |
| SE424865B (en) | 1982-08-16 |
| FR2244506A1 (en) | 1975-04-18 |
| DE2429562A1 (en) | 1975-01-16 |
| LU70403A1 (en) | 1975-03-27 |
| NL7408489A (en) | 1974-12-30 |
| NO742310L (en) | 1975-01-20 |
| FR2244506B1 (en) | 1977-02-25 |
| DK341274A (en) | 1975-02-24 |
| CH592642A5 (en) | 1977-10-31 |
| CA1019749A (en) | 1977-10-25 |
| GB1425429A (en) | 1976-02-18 |
| NO143531C (en) | 1981-03-11 |
| IL45113A0 (en) | 1974-09-10 |
| NL179135B (en) | 1986-02-17 |
| JPS5922711B2 (en) | 1984-05-28 |
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