GB593024A - Production of ª‰-2-thienoylpropionic acids and derivatives thereof - Google Patents
Production of ª‰-2-thienoylpropionic acids and derivatives thereofInfo
- Publication number
- GB593024A GB593024A GB951644A GB951644A GB593024A GB 593024 A GB593024 A GB 593024A GB 951644 A GB951644 A GB 951644A GB 951644 A GB951644 A GB 951644A GB 593024 A GB593024 A GB 593024A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromo
- acids
- acid
- alkyl
- methyl
- 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
- 239000002253 acid Substances 0.000 title abstract 14
- 150000007513 acids Chemical class 0.000 title abstract 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 14
- 239000001187 sodium carbonate Substances 0.000 abstract 7
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N Thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 4
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 abstract 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N Methylcarbamodithioic acid K salt Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- IYKVLICPFCEZOF-UHFFFAOYSA-N Selenourea Chemical compound NC(N)=[Se] IYKVLICPFCEZOF-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- -1 ethylphenyl isopropylphenyl Chemical group 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 229940014800 succinic anhydride Drugs 0.000 abstract 2
- KIGWTSCMRIXWMR-UHFFFAOYSA-N 2-(2-amino-4-phenyl-1,3-selenazol-5-yl)acetic acid Chemical compound [se]1C(N)=NC(C=2C=CC=CC=2)=C1CC(O)=O KIGWTSCMRIXWMR-UHFFFAOYSA-N 0.000 abstract 1
- JSYNROPGKZVGRJ-UHFFFAOYSA-N 2-(4-phenyl-1,3-thiazol-5-yl)acetic acid Chemical compound S1C=NC(C=2C=CC=CC=2)=C1CC(=O)O JSYNROPGKZVGRJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- XCNLOAQUZHKKFH-UHFFFAOYSA-N C1(=CC=CC=C1)C=1N=C(SC1CC(=O)OC)C Chemical compound C1(=CC=CC=C1)C=1N=C(SC1CC(=O)OC)C XCNLOAQUZHKKFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N Phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000001476 alcoholic Effects 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 abstract 1
- UEALQOSQARFHSD-UHFFFAOYSA-N methyl 2-(2-amino-4-phenyl-1,3-thiazol-5-yl)acetate Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1CC(=O)OC UEALQOSQARFHSD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 239000011669 selenium Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000005023 xylyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/02—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms not condensed with other rings
- C07D293/04—Five-membered rings
- C07D293/06—Selenazoles; Hydrogenated selenazoles
Abstract
4-Arylthiazole- and -selenazole-5-acetic acids and esters and 4-(21-thienyl)-thiazole-5-acetic acids and esters, of the general formula <FORM:0593024/IV/1> where R1 is an aryl group (which may contain nuclear substituents, e.g. a phenyl, tolyl, naphthyl, ethylphenyl isopropylphenyl, xylyl, anisyl, phenetyl or chlorophenyl group) or a 2-thienyl group, R2 is hydrogen or an alkyl or aryl group, R3 is hydrogen or a hydrocarbon radical, R' is hydrogen or an alkyl, alkylthio, aralkylthio or amino group, and X is sulphur or (when R1 is aryl and R' is amino) selenium, are manufactured by condensing b -halogen-b -aryl- or -b -2-thenyl-propionic acids or esters or a -alkyl- or a -aryl derivatives thereof with thiourea, thioamides of aliphatic monocarboxylic acids, or S-alkyl or S-aralkyl dithiocarbamates, or condensing b -halogen-b -arylpropionic acids or esters or a -alkyl or a -aryl derivative thereof with selenourea. The reaction may be effected by bringing the reactants together in a solvent, with heating if necessary and preferably in the presence of alkalis, e.g. alkali carbonates or bicarbonates. In examples: (1) b -bromo-b -benzoylpropionic acid is shaken with an ethereal solution of thioformamide (prepared by the action of phosphorus pentasulphide on formamide in ether) to produce 4-phenylthiazole-5-acetic acid; (2) 4-phenyl-, 4 - (41 - methyl-, -ethyl-, -isopropyl-, -methoxy-and -chloro-phenyl)- and 4-(21 : 41 - dimethylphenyl) - 2 - methylthiazole - 5 - acetic acids are prepared by the action of thioacetamide on the appropriate b -bromo-b -aroylpropionic acids in isopropyl alcohol with the addition of sodium carbonate; (3) b -bromo-b -thienoyl propionic acid and thioacetamide are dissolved in isopropyl alcohol and allowed to stand, and the resulting hydrobromide is treated with aqueous sodium hydroxide to liberate 4-(21-thienyl)-2-methylthiazole-5-acetic acid; (4) and (5) b -bromo-b -(1- and 2-naphthoyl)-propionic acids are treated as in (2) to give 4-(11-and 21 - naphthyl) - 2 - methylthiazole - 5 - acetic acids; (6) b -bromo-b -benzoylisobutyric acid is treated with thioacetamide in ethanol in the presence of sodium carbonate to yield a - 5 - (4 - phenyl - 2 - methylthiazole) - propionic acid; (7) methyl b -bromo-b -benzoylpropionate is refluxed with thioacetamide in ethyl alcohol with the addition of sodium carbonate to form methyl 4-phenyl-2-methylthiazole-5-acetate, which may be converted to the free acid by heating with aqueous alcoholic potassium hydroxide; (8) 4-phenyl- and 4 - (41 - methylphenyl) - 2 - aminothiazole - 5 - acetic acids are prepared by heating the appropriate b - bromo - b - aroylpropionic acids with thiourea in isopropyl alcohol with the addition of sodium carbonate; (9) b -bromo-b -thienoylpropionic acid similarly yields 2-amino-4-(21-thienyl)-thiazole-5-acetic acid; (10) and (11) b - bromo - b - (1- and 2-naphthoyl)-propionic acids similarly give 2-amino-4-(11- and 21-naphthyl) - thiazole - 5 - acetic acids; (12) the thioacetamide in (6) is replaced by thiourea, producing a - 5 - (2 - amino - 4 - phenylthiazole)-propionic acid; (13) methyl b -bromo-b -benzoylpropionate is heated with thiourea in isopropyl alcohol in the presence of sodium carbonate to produce methyl-2-amino-4-phenylthiazole-5-acetate, which may be hydrolysed as in (7); (14) 2-methylthio- and 2-ethylthio-4-phenyl- and 2-methylthio-4-(41-methylphenyl)-thiazole-5-acetic acids are prepared by treating the appropriate b -bromo-b -aroylpropionic acids in the cold with the appropriate S-alkyl dithiocarbamates in isopropyl alcohol; (15) b -bromo-b -(1-naphthoyl)-propionic acid is treated with methyl dithiocarbamate in isopropyl alcohol with the addition of sodium carbonate, producing 2 - methylthio - 4 - (11 - naphthyl) - thiazole - 5 - acetic acid; (16) b - bromo - b - (2 - naphthoyl) - propionic acid is treated in the cold with methyl dithiocarbamate in isopropyl alcohol, and 2-methylthio-4-(21-naphthyl)-thiazole-5-acetic acid is liberated from the resulting hydrobromide; (17) b -bromo-b -benzoylpropionic acid is heated with selenourea in isopropyl alcohol in the presence of sodium carbonate, yielding 2-amino-4-phenylselenazole-5-acetic acid. b - Bromo - b - aroylpropionic acids, their a -alkyl and a aryl derivatives and b -bromo-b -2-thienylpropionic acid are obtainable by treating the corresponding non-brominated acids with an equimolecular proportion of bromine using chloroform as solvent, e.g. by gradual addition of bromine to a boiling solution or suspension of the acid in chloroform. Examples are given of the preparation of the b -bromo-derivatives of b -(1- and 2-naphthoyl)- propionic acids and b - 2 - thienoylpropionic acid. b -(1- and 2-Naphthoyl)-propionic acids are obtainable by condensing naphthalene with succinic anhydride in nitrobenzene in the presence of aluminium chloride. An example is given of the separation of the isomers from the resulting mixture. a -Alkyl- and a -aryl-b -aroylpropionic acids are obtainable by Friedel-Crafts condensation of alkyl and aryl substituted succinic anhydrides with aromatic hydrocarbons, e.g. of methylsuccinic anhydride with benzene to give b -benzoylisobutyric acid. b - 2 - Thienoylpropionic acid is obtainable by condensing thiophene with succinic anhydride in nitrobenzene in the presence of aluminium chloride. Methyl b -bromo-b -benzoylpropionate is obtainable by esterifying b -benzoylpropionic acid with methyl alcohol in the presence of sulphuric acid and treating the ester with bromine in chloroform solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR950290D FR950290A (en) | 1944-05-18 | 1946-08-29 | Process for the preparation of 4-arylthiazol (and selenazol) -5-acetic acids and their esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB593024A true GB593024A (en) | 1947-10-07 |
Family
ID=1629846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB951644A Expired GB593024A (en) | 1944-05-18 | 1944-05-18 | Production of ª‰-2-thienoylpropionic acids and derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB593024A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034340A1 (en) * | 1980-02-18 | 1981-08-26 | Lonza Ag | Process for the production of (2-amino-thiazol-4-yl) acetic acid hydrochloride |
-
1944
- 1944-05-18 GB GB951644A patent/GB593024A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0034340A1 (en) * | 1980-02-18 | 1981-08-26 | Lonza Ag | Process for the production of (2-amino-thiazol-4-yl) acetic acid hydrochloride |
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