DE3228549A1 - Chromon-3-sulfinsaeuren und verfahren zu ihrer herstellung - Google Patents
Chromon-3-sulfinsaeuren und verfahren zu ihrer herstellungInfo
- Publication number
- DE3228549A1 DE3228549A1 DE19823228549 DE3228549A DE3228549A1 DE 3228549 A1 DE3228549 A1 DE 3228549A1 DE 19823228549 DE19823228549 DE 19823228549 DE 3228549 A DE3228549 A DE 3228549A DE 3228549 A1 DE3228549 A1 DE 3228549A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- chromone
- acetophenone
- thionyl chloride
- preparation
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title abstract description 6
- 150000007513 acids Chemical class 0.000 title abstract description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- -1 enamine ketones Chemical class 0.000 abstract description 18
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- BOEMGPJOKXQOAS-UHFFFAOYSA-N 2-[(4-oxochromen-2-yl)disulfanyl]chromen-4-one Chemical class O1C(=CC(C2=CC=CC=C12)=O)SSC=1OC2=CC=CC=C2C(C=1)=O BOEMGPJOKXQOAS-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical class OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LYKDOWJROLHYOT-UHFFFAOYSA-N 1-(2-hydroxy-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C)C=C1O LYKDOWJROLHYOT-UHFFFAOYSA-N 0.000 description 2
- MLIBGOFSXXWRIY-UHFFFAOYSA-N 1-(2-hydroxy-5-methoxyphenyl)ethanone Chemical compound COC1=CC=C(O)C(C(C)=O)=C1 MLIBGOFSXXWRIY-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- MOXXPQWMYMUHHV-UHFFFAOYSA-N diethoxymethanol Chemical compound CCOC(O)OCC MOXXPQWMYMUHHV-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- NZAVQJCDRYONGJ-UHFFFAOYSA-N 1-(1-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone Chemical compound C1CCCC2=C(O)C(C(=O)C)=CC=C21 NZAVQJCDRYONGJ-UHFFFAOYSA-N 0.000 description 1
- ZKCHVINHDAVKLD-UHFFFAOYSA-N 1-(10-hydroxyphenanthren-9-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(O)C3=CC=CC=C3C2=C1 ZKCHVINHDAVKLD-UHFFFAOYSA-N 0.000 description 1
- AGQNLHOTLJFJCG-UHFFFAOYSA-N 1-(2-hydroxy-4-phenylmethoxyphenyl)ethanone Chemical compound C1=C(O)C(C(=O)C)=CC=C1OCC1=CC=CC=C1 AGQNLHOTLJFJCG-UHFFFAOYSA-N 0.000 description 1
- UJPXBWSJJVPTTJ-UHFFFAOYSA-N 1-(2-hydroxy-5-phenylphenyl)ethanone Chemical group C1=C(O)C(C(=O)C)=CC(C=2C=CC=CC=2)=C1 UJPXBWSJJVPTTJ-UHFFFAOYSA-N 0.000 description 1
- WLIIRQPHHPHJEB-UHFFFAOYSA-N 1-(2-hydroxy-6-methylnaphthalen-1-yl)ethanone Chemical compound OC=1C(=C2C=CC(=CC2=CC1)C)C(C)=O WLIIRQPHHPHJEB-UHFFFAOYSA-N 0.000 description 1
- RNUOGAGFYMYERZ-UHFFFAOYSA-N 1-(2-hydroxyphenanthren-1-yl)ethanone Chemical compound OC1=C(C=2C=CC3=CC=CC=C3C2C=C1)C(C)=O RNUOGAGFYMYERZ-UHFFFAOYSA-N 0.000 description 1
- CJFYGRLJDKWMDI-UHFFFAOYSA-N 1-(3,5-dichloro-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(Cl)=C1O CJFYGRLJDKWMDI-UHFFFAOYSA-N 0.000 description 1
- BPQABGQSVOUODJ-UHFFFAOYSA-N 1-(4-bromo-2-hydroxy-5-methylphenyl)ethanone Chemical compound CC(=O)C1=CC(C)=C(Br)C=C1O BPQABGQSVOUODJ-UHFFFAOYSA-N 0.000 description 1
- VBLALYJSGGGWHU-UHFFFAOYSA-N 1-(4-ethoxy-2-hydroxyphenyl)ethanone Chemical compound CCOC1=CC=C(C(C)=O)C(O)=C1 VBLALYJSGGGWHU-UHFFFAOYSA-N 0.000 description 1
- GEYCQLIOGQPPFM-UHFFFAOYSA-N 1-(5-acetyl-2,4-dihydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(C(C)=O)=C(O)C=C1O GEYCQLIOGQPPFM-UHFFFAOYSA-N 0.000 description 1
- XRHLZWNTCOKXCJ-UHFFFAOYSA-N 1-(5-acetyl-2,6-dihydroxynaphthalen-1-yl)ethanone Chemical compound OC1=CC=C2C(C(=O)C)=C(O)C=CC2=C1C(C)=O XRHLZWNTCOKXCJ-UHFFFAOYSA-N 0.000 description 1
- HQCCNFFIOWYINW-UHFFFAOYSA-N 1-(5-bromo-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Br)=CC=C1O HQCCNFFIOWYINW-UHFFFAOYSA-N 0.000 description 1
- HDUSGGZSLVCDKY-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-4-methylphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=C(C)C=C1O HDUSGGZSLVCDKY-UHFFFAOYSA-N 0.000 description 1
- XTGCUDZCCIRWHL-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1O XTGCUDZCCIRWHL-UHFFFAOYSA-N 0.000 description 1
- GEUAWNMVARSYHO-UHFFFAOYSA-N 1-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)ethanone Chemical compound COC1=C(O)C(C(C)=O)=C(OC)C2=C1OC=C2 GEUAWNMVARSYHO-UHFFFAOYSA-N 0.000 description 1
- YPTJKHVBDCRKNF-UHFFFAOYSA-N 2',6'-Dihydroxyacetophenone Chemical compound CC(=O)C1=C(O)C=CC=C1O YPTJKHVBDCRKNF-UHFFFAOYSA-N 0.000 description 1
- YNPDFBFVMJNGKZ-UHFFFAOYSA-N 2'-Hydroxy-5'-methylacetophenone Chemical compound CC(=O)C1=CC(C)=CC=C1O YNPDFBFVMJNGKZ-UHFFFAOYSA-N 0.000 description 1
- KMQOVBGBIGYRIL-UHFFFAOYSA-N 2-(4-hydroxycyclohexyl)-1-phenylethanone Chemical compound OC1CCC(CC1)CC(=O)C1=CC=CC=C1 KMQOVBGBIGYRIL-UHFFFAOYSA-N 0.000 description 1
- GWFBKWHPRHMWGH-UHFFFAOYSA-N 2-hydroxy-1-(2-nitrophenyl)ethanone Chemical compound OCC(=O)C1=CC=CC=C1[N+]([O-])=O GWFBKWHPRHMWGH-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- AYAFDQIOLUUJHW-UHFFFAOYSA-N 6-acetyl-7-hydroxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=C(C(=O)C)C(O)=C2 AYAFDQIOLUUJHW-UHFFFAOYSA-N 0.000 description 1
- NQPNQSQEVKTACY-UHFFFAOYSA-N 6-methyl-4-oxochromene-3-sulfinic acid Chemical compound O1C=C(S(O)=O)C(=O)C2=CC(C)=CC=C21 NQPNQSQEVKTACY-UHFFFAOYSA-N 0.000 description 1
- WZOMQVFUPMLOGT-UHFFFAOYSA-N 8-acetyl-7-hydroxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=CC(O)=C2C(=O)C WZOMQVFUPMLOGT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- QXMLXIVCCJYRBA-UHFFFAOYSA-N OC1=C(C2=CC=C3CCCCC3=C2C=C1)C(C)=O Chemical compound OC1=C(C2=CC=C3CCCCC3=C2C=C1)C(C)=O QXMLXIVCCJYRBA-UHFFFAOYSA-N 0.000 description 1
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 150000004777 chromones Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228549 DE3228549A1 (de) | 1982-07-30 | 1982-07-30 | Chromon-3-sulfinsaeuren und verfahren zu ihrer herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228549 DE3228549A1 (de) | 1982-07-30 | 1982-07-30 | Chromon-3-sulfinsaeuren und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3228549A1 true DE3228549A1 (de) | 1984-02-02 |
| DE3228549C2 DE3228549C2 (enrdf_load_stackoverflow) | 1988-12-15 |
Family
ID=6169751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823228549 Granted DE3228549A1 (de) | 1982-07-30 | 1982-07-30 | Chromon-3-sulfinsaeuren und verfahren zu ihrer herstellung |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3228549A1 (enrdf_load_stackoverflow) |
-
1982
- 1982-07-30 DE DE19823228549 patent/DE3228549A1/de active Granted
Non-Patent Citations (3)
| Title |
|---|
| Arch. Pharm., 315, 1982, S.892-893 * |
| Ber. Dtsch. Chem. Ges., 71, 1938, S.106-113 * |
| Chem. Ber., 104, 1971, S.348-349 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3228549C2 (enrdf_load_stackoverflow) | 1988-12-15 |
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