NO763144L - Fremgangsm}te ved fremstilling av 2-nitro-3-fenyl-benzofuranderivater. - Google Patents
Fremgangsm}te ved fremstilling av 2-nitro-3-fenyl-benzofuranderivater.Info
- Publication number
- NO763144L NO763144L NO763144A NO763144A NO763144L NO 763144 L NO763144 L NO 763144L NO 763144 A NO763144 A NO 763144A NO 763144 A NO763144 A NO 763144A NO 763144 L NO763144 L NO 763144L
- Authority
- NO
- Norway
- Prior art keywords
- nitro
- acid
- phenyl
- compound according
- benzofuranacetic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 5
- AROVMVPUPBWOAS-UHFFFAOYSA-N 2-nitro-3-phenyl-1-benzofuran Chemical class [O-][N+](=O)C=1OC2=CC=CC=C2C=1C1=CC=CC=C1 AROVMVPUPBWOAS-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 42
- -1 nitro, phenyl Chemical group 0.000 claims description 25
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 238000006396 nitration reaction Methods 0.000 claims description 9
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- JAFHKQUFCVEPEY-UHFFFAOYSA-N 2-(2-nitro-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical group OC(=O)CC1([N+]([O-])=O)OC2=CC=CC2=CC1C1=CC=CC=C1 JAFHKQUFCVEPEY-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- KHZXISCMFGRTFU-UHFFFAOYSA-N 2-nitro-3-phenyl-3h-1-benzofuran-2-carbaldehyde Chemical compound [O-][N+](=O)C1(C=O)OC2=CC=CC=C2C1C1=CC=CC=C1 KHZXISCMFGRTFU-UHFFFAOYSA-N 0.000 claims description 3
- JBHISCWFNYSIHQ-UHFFFAOYSA-N 3-(2-nitro-3-phenyl-3h-cyclopenta[b]pyran-2-yl)propanoic acid Chemical group OC(=O)CCC1([N+]([O-])=O)OC2=CC=CC2=CC1C1=CC=CC=C1 JBHISCWFNYSIHQ-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- PEDBJRVYZLCZRD-UHFFFAOYSA-N 3-(2-nitro-3-phenyl-3h-1-benzofuran-2-yl)propanoic acid Chemical compound OC(=O)CCC1([N+]([O-])=O)OC2=CC=CC=C2C1C1=CC=CC=C1 PEDBJRVYZLCZRD-UHFFFAOYSA-N 0.000 claims description 2
- ZBSLKAYNXNYAOC-UHFFFAOYSA-N 3-phenyl-1-benzofuran-2-carbaldehyde Chemical compound O=CC=1OC2=CC=CC=C2C=1C1=CC=CC=C1 ZBSLKAYNXNYAOC-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 150000002826 nitrites Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- XDJKSKGUDKHOOF-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)-2-nitro-3h-cyclopenta[b]pyran-2-yl]acetic acid Chemical group OC(=O)CC1([N+]([O-])=O)OC2=CC=CC2=CC1C1=CC=C(F)C=C1 XDJKSKGUDKHOOF-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 67
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000845 anti-microbial effect Effects 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 229920000137 polyphosphoric acid Polymers 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- MJBZHKDQFMFYEI-UHFFFAOYSA-N 2-(2-bromo-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC1(Br)OC2=CC=CC2=CC1C1=CC=CC=C1 MJBZHKDQFMFYEI-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 150000008062 acetophenones Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000813 microbial effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- VGSDHJAXIRBARN-UHFFFAOYSA-N 2-(2,7-dibromo-3-phenyl-1-benzofuran-5-yl)acetonitrile Chemical compound BrC=1OC2=C(Br)C=C(CC#N)C=C2C=1C1=CC=CC=C1 VGSDHJAXIRBARN-UHFFFAOYSA-N 0.000 description 2
- VDDWNEZEAFDTNH-UHFFFAOYSA-N 2-(2-bromo-3-phenyl-1-benzofuran-4-yl)acetonitrile Chemical compound BrC=1OC2=CC=CC(CC#N)=C2C=1C1=CC=CC=C1 VDDWNEZEAFDTNH-UHFFFAOYSA-N 0.000 description 2
- RFBIATJJCXJSTO-UHFFFAOYSA-N 2-(2-iodo-3-phenyl-3h-cyclopenta[b]pyran-2-yl)acetic acid Chemical compound OC(=O)CC1(I)OC2=CC=CC2=CC1C1=CC=CC=C1 RFBIATJJCXJSTO-UHFFFAOYSA-N 0.000 description 2
- SWORVQXZNIJIOP-UHFFFAOYSA-N 2-(2-nitro-3-phenyl-1-benzofuran-5-yl)acetic acid Chemical compound C12=CC(CC(=O)O)=CC=C2OC([N+]([O-])=O)=C1C1=CC=CC=C1 SWORVQXZNIJIOP-UHFFFAOYSA-N 0.000 description 2
- OPIQODRGVGQICO-UHFFFAOYSA-N 2-(2-nitro-3-phenyl-1-benzofuran-5-yl)acetonitrile Chemical compound [O-][N+](=O)C=1OC2=CC=C(CC#N)C=C2C=1C1=CC=CC=C1 OPIQODRGVGQICO-UHFFFAOYSA-N 0.000 description 2
- QZJULIXUNKVGQQ-UHFFFAOYSA-N 2-(3-methylphenoxy)-1-phenylethanone Chemical compound CC1=CC=CC(OCC(=O)C=2C=CC=CC=2)=C1 QZJULIXUNKVGQQ-UHFFFAOYSA-N 0.000 description 2
- OKJTYCKLDHIPPK-UHFFFAOYSA-N 2-(3-phenylcyclopenta[c]pyran-1-yl)acetic acid Chemical compound C=1C2=CC=CC2=C(CC(=O)O)OC=1C1=CC=CC=C1 OKJTYCKLDHIPPK-UHFFFAOYSA-N 0.000 description 2
- QEKMYRNSCCJRAU-UHFFFAOYSA-N 2-(7-bromo-2-nitro-3-phenyl-1-benzofuran-5-yl)acetonitrile Chemical compound [O-][N+](=O)C=1OC2=C(Br)C=C(CC#N)C=C2C=1C1=CC=CC=C1 QEKMYRNSCCJRAU-UHFFFAOYSA-N 0.000 description 2
- IFLCHKZVHQMOTC-UHFFFAOYSA-N 2-[2-bromo-3-(2-fluorophenyl)-4-methoxy-1-benzofuran-7-yl]acetonitrile Chemical compound C1=2C(OC)=CC=C(CC#N)C=2OC(Br)=C1C1=CC=CC=C1F IFLCHKZVHQMOTC-UHFFFAOYSA-N 0.000 description 2
- YROAKUOQAPZBNY-UHFFFAOYSA-N 2-[2-bromo-3-(2-fluorophenyl)-4-methoxy-3h-cyclopenta[b]pyran-2-yl]acetic acid Chemical compound COC1=C2C=CC=C2OC(Br)(CC(O)=O)C1C1=CC=CC=C1F YROAKUOQAPZBNY-UHFFFAOYSA-N 0.000 description 2
- BILXPNSGLNPLLM-UHFFFAOYSA-N 2-[3-(4-cyanophenyl)cyclopenta[c]pyran-1-yl]acetic acid Chemical compound C=1C2=CC=CC2=C(CC(=O)O)OC=1C1=CC=C(C#N)C=C1 BILXPNSGLNPLLM-UHFFFAOYSA-N 0.000 description 2
- SUNQAAGGQUMIFW-UHFFFAOYSA-N 2-[3-(4-phenylphenyl)cyclopenta[c]pyran-1-yl]acetic acid Chemical compound C=1C2=CC=CC2=C(CC(=O)O)OC=1C(C=C1)=CC=C1C1=CC=CC=C1 SUNQAAGGQUMIFW-UHFFFAOYSA-N 0.000 description 2
- DJAFZEXZBHSVKL-UHFFFAOYSA-N 2-bromo-4-(bromomethyl)-3-phenyl-1-benzofuran Chemical compound C1=2C(CBr)=CC=CC=2OC(Br)=C1C1=CC=CC=C1 DJAFZEXZBHSVKL-UHFFFAOYSA-N 0.000 description 2
- HNZRVKGAUIDWRC-UHFFFAOYSA-N 2-bromo-4-methyl-3-phenyl-1-benzofuran Chemical compound C1=2C(C)=CC=CC=2OC(Br)=C1C1=CC=CC=C1 HNZRVKGAUIDWRC-UHFFFAOYSA-N 0.000 description 2
- SORAXUUZQGMHDC-UHFFFAOYSA-N 2-bromo-5-(bromomethyl)-3-phenyl-1-benzofuran Chemical group C12=CC(CBr)=CC=C2OC(Br)=C1C1=CC=CC=C1 SORAXUUZQGMHDC-UHFFFAOYSA-N 0.000 description 2
- CCCGLIZAQCPMBD-UHFFFAOYSA-N 2-bromo-6-methyl-3-phenyl-1-benzofuran Chemical compound BrC=1OC2=CC(C)=CC=C2C=1C1=CC=CC=C1 CCCGLIZAQCPMBD-UHFFFAOYSA-N 0.000 description 2
- ZWDCJLOMRWYSCN-UHFFFAOYSA-N 2-bromo-7-(bromomethyl)-3-(2-fluorophenyl)-4-methoxy-1-benzofuran Chemical compound C1=2C(OC)=CC=C(CBr)C=2OC(Br)=C1C1=CC=CC=C1F ZWDCJLOMRWYSCN-UHFFFAOYSA-N 0.000 description 2
- SBRNQLHGSVPRLM-UHFFFAOYSA-N 2-nitro-3-phenyl-1-benzofuran-7-carbaldehyde Chemical compound [O-][N+](=O)C=1OC2=C(C=O)C=CC=C2C=1C1=CC=CC=C1 SBRNQLHGSVPRLM-UHFFFAOYSA-N 0.000 description 2
- SVXXDGOWGXUSLS-UHFFFAOYSA-N 3-(2-fluorophenyl)-4-methoxy-7-methyl-1-benzofuran Chemical compound C1=2C(OC)=CC=C(C)C=2OC=C1C1=CC=CC=C1F SVXXDGOWGXUSLS-UHFFFAOYSA-N 0.000 description 2
- UXOCJHANNJEISD-UHFFFAOYSA-N 3-(2-nitro-3-phenyl-3h-1-benzofuran-2-yl)prop-2-enoic acid Chemical compound OC(=O)C=CC1([N+]([O-])=O)OC2=CC=CC=C2C1C1=CC=CC=C1 UXOCJHANNJEISD-UHFFFAOYSA-N 0.000 description 2
- WGVCJKNNOCSSTL-UHFFFAOYSA-N 3-phenyl-1-benzofuran-2-carbonitrile Chemical compound N#CC=1OC2=CC=CC=C2C=1C1=CC=CC=C1 WGVCJKNNOCSSTL-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Inorganic materials [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61627775A | 1975-09-24 | 1975-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO763144L true NO763144L (no) | 1977-03-25 |
Family
ID=24468746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763144A NO763144L (no) | 1975-09-24 | 1976-09-14 | Fremgangsm}te ved fremstilling av 2-nitro-3-fenyl-benzofuranderivater. |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5239666A (xx) |
| AR (1) | AR215598A1 (xx) |
| AU (1) | AU1804276A (xx) |
| BE (1) | BE846502A (xx) |
| CS (1) | CS191319B2 (xx) |
| DD (1) | DD130786A5 (xx) |
| DE (1) | DE2642840A1 (xx) |
| DK (1) | DK413676A (xx) |
| EG (1) | EG12427A (xx) |
| ES (1) | ES451542A1 (xx) |
| FI (1) | FI762715A (xx) |
| FR (1) | FR2325369A1 (xx) |
| IL (1) | IL50543A0 (xx) |
| IT (1) | IT1070556B (xx) |
| NL (1) | NL7610166A (xx) |
| NO (1) | NO763144L (xx) |
| OA (1) | OA05441A (xx) |
| PT (1) | PT65632B (xx) |
| SE (1) | SE7610149L (xx) |
| SU (1) | SU692561A3 (xx) |
| ZA (1) | ZA765079B (xx) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143152A (en) | 1977-12-19 | 1979-03-06 | Riker Laboratories, Inc. | Anti-microbial (2-nitro-3-phenyl benzofuranyl)-phenylalkanoic acids and derivatives |
| US4128659A (en) | 1977-12-19 | 1978-12-05 | Riker Laboratories, Inc. | Antimicrobial polycyclic nitrofurans |
| US4153721A (en) | 1977-12-19 | 1979-05-08 | Riker Laboratories, Inc. | Derivatives of 2-nitrobenzofuran |
| US4174403A (en) | 1978-06-26 | 1979-11-13 | Riker Laboratories, Inc. | 5,6-Methylenedioxy-2-nitro-3-phenylbenzofurans |
| US4154847A (en) | 1978-06-26 | 1979-05-15 | Riker Laboratories, Inc. | Derivatives of 2-nitro-3-phenylbenzofurancarboxaldehydes |
| AU2020348754A1 (en) * | 2019-09-16 | 2022-04-14 | Koda Therapeutics, LLC | Antimicrobial agents and compositions and uses thereof |
-
1976
- 1976-08-24 ZA ZA765079A patent/ZA765079B/xx unknown
- 1976-09-14 NL NL7610166A patent/NL7610166A/xx not_active Application Discontinuation
- 1976-09-14 DK DK413676A patent/DK413676A/da unknown
- 1976-09-14 SE SE7610149A patent/SE7610149L/xx unknown
- 1976-09-14 NO NO763144A patent/NO763144L/no unknown
- 1976-09-15 ES ES451542A patent/ES451542A1/es not_active Expired
- 1976-09-23 DE DE19762642840 patent/DE2642840A1/de active Pending
- 1976-09-23 CS CS766174A patent/CS191319B2/cs unknown
- 1976-09-23 FI FI762715A patent/FI762715A/fi not_active Application Discontinuation
- 1976-09-23 IL IL50543A patent/IL50543A0/xx unknown
- 1976-09-23 AR AR264829A patent/AR215598A1/es active
- 1976-09-23 DD DD7600194956A patent/DD130786A5/xx unknown
- 1976-09-23 BE BE170876A patent/BE846502A/xx unknown
- 1976-09-23 SU SU762405875A patent/SU692561A3/ru active
- 1976-09-23 OA OA55942A patent/OA05441A/xx unknown
- 1976-09-23 PT PT65632A patent/PT65632B/pt unknown
- 1976-09-23 FR FR7628662A patent/FR2325369A1/fr active Granted
- 1976-09-23 AU AU18042/76A patent/AU1804276A/en not_active Expired
- 1976-09-23 IT IT27552/76A patent/IT1070556B/it active
- 1976-09-24 JP JP51114551A patent/JPS5239666A/ja active Pending
- 1976-09-28 EG EG592/76A patent/EG12427A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| FI762715A (xx) | 1977-03-25 |
| DK413676A (da) | 1977-03-25 |
| CS191319B2 (en) | 1979-06-29 |
| SE7610149L (sv) | 1977-03-25 |
| FR2325369A1 (fr) | 1977-04-22 |
| DE2642840A1 (de) | 1977-04-07 |
| NL7610166A (nl) | 1977-03-28 |
| PT65632B (en) | 1978-04-05 |
| SU692561A3 (ru) | 1979-10-15 |
| AU1804276A (en) | 1978-04-06 |
| EG12427A (en) | 1979-03-31 |
| IT1070556B (it) | 1985-03-29 |
| DD130786A5 (de) | 1978-05-03 |
| JPS5239666A (en) | 1977-03-28 |
| BE846502A (fr) | 1977-03-23 |
| AR215598A1 (es) | 1979-10-31 |
| FR2325369B1 (xx) | 1979-02-23 |
| ZA765079B (en) | 1977-08-31 |
| ES451542A1 (es) | 1977-10-01 |
| IL50543A0 (en) | 1976-11-30 |
| PT65632A (en) | 1976-10-01 |
| OA05441A (fr) | 1981-03-31 |
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