JP2009179607A - イソインドール類の製造方法、及びイソインドール類の製造方法によって製造されるイソインドール類 - Google Patents
イソインドール類の製造方法、及びイソインドール類の製造方法によって製造されるイソインドール類 Download PDFInfo
- Publication number
- JP2009179607A JP2009179607A JP2008020310A JP2008020310A JP2009179607A JP 2009179607 A JP2009179607 A JP 2009179607A JP 2008020310 A JP2008020310 A JP 2008020310A JP 2008020310 A JP2008020310 A JP 2008020310A JP 2009179607 A JP2009179607 A JP 2009179607A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- linear
- isoindoles
- sulfonic acid
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
- 150000002518 isoindoles Chemical class 0.000 title abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 56
- GBPPYKCVWZEJBD-UHFFFAOYSA-N bicyclo[2.2.2]octa-1,3-diene Chemical group C1=C(CC2)CCC2=C1 GBPPYKCVWZEJBD-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 32
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 28
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 322
- 125000003342 alkenyl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 65
- -1 cyclic alkene Chemical class 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 58
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 52
- 125000004122 cyclic group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 46
- 125000002252 acyl group Chemical group 0.000 claims description 41
- 125000004423 acyloxy group Chemical group 0.000 claims description 41
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 36
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 36
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 36
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 36
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 34
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 32
- 125000004442 acylamino group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 28
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 28
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 28
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 28
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 28
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 28
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 28
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 125000000565 sulfonamide group Chemical group 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 19
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 claims description 11
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 9
- 150000007942 carboxylates Chemical group 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 13
- 125000002950 monocyclic group Chemical group 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000003944 tolyl group Chemical group 0.000 description 9
- 125000005023 xylyl group Chemical group 0.000 description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 7
- 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 7
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000006038 hexenyl group Chemical group 0.000 description 7
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- GZEFZLXJPGMRSP-UHFFFAOYSA-N 37,38,39,40-tetrazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),2,4,6,8,10,12(39),13,15,17,19,21,23,25,27,29,31,33,35-nonadecaene Chemical compound c1ccc2c3cc4[nH]c(cc5nc(cc6[nH]c(cc(n3)c2c1)c1ccccc61)c1ccccc51)c1ccccc41 GZEFZLXJPGMRSP-UHFFFAOYSA-N 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 4
- QTYUSOHYEPOHLV-UHFFFAOYSA-N octadiene group Chemical group C=CC=CCCCC QTYUSOHYEPOHLV-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000002428 photodynamic therapy Methods 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 C**(C(*)(CC1)C2=C(*3C)C(N)=C(*)C4=C([C@@](C)C(O)=C(*5C)C(C6(*)C(*)=C(*)CCC6)=C(*)C5=C5I)C(*)(CC6)C(*)=C(*)C46I)=*C1(*)C2=C3C(N)=C1C(C2(*)C(*)=C(*)C3(*)CC2)=C3C5=*1 Chemical compound C**(C(*)(CC1)C2=C(*3C)C(N)=C(*)C4=C([C@@](C)C(O)=C(*5C)C(C6(*)C(*)=C(*)CCC6)=C(*)C5=C5I)C(*)(CC6)C(*)=C(*)C46I)=*C1(*)C2=C3C(N)=C1C(C2(*)C(*)=C(*)C3(*)CC2)=C3C5=*1 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006742 Retro-Diels-Alder reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- YIJOASXMXJOMPB-UHFFFAOYSA-N ctk0j9514 Chemical compound C1CC2C3=C(C(=O)OCC)NC=C3C1C=C2 YIJOASXMXJOMPB-UHFFFAOYSA-N 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- BVPSSFSWWXSMKD-UHFFFAOYSA-N ethyl 2h-isoindole-1-carboxylate Chemical compound C1=CC=CC2=C(C(=O)OCC)NC=C21 BVPSSFSWWXSMKD-UHFFFAOYSA-N 0.000 description 1
- PXCRBIHOQRKFQU-UHFFFAOYSA-N ethyl 3-chloro-2h-isoindole-1-carboxylate Chemical compound C1=CC=CC2=C(C(=O)OCC)NC(Cl)=C21 PXCRBIHOQRKFQU-UHFFFAOYSA-N 0.000 description 1
- FYPYPBVBWZLKEH-UHFFFAOYSA-N ethyl 5-chloro-4-azatricyclo[5.2.2.02,6]undeca-2,5,8-triene-3-carboxylate Chemical compound C1CC2C3=C(C(=O)OCC)NC(Cl)=C3C1C=C2 FYPYPBVBWZLKEH-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Abstract
【解決手段】ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物を、超臨界二酸化炭素雰囲気下で保持する熱処理工程を有するイソインドール類の製造方法とすることによって、上記課題を解決する。
【選択図】なし
Description
R.Bonnett and R.F.C.Brown,"Isoindole"Chem.Commun.,393−395,1972, J.Bornstein,D.E.Remy and J.E.Shields,"Synthesis of isoindole by retro−Diels−Alder reaction"Chem.Commun.,1149−1150,1972 H.Uno,S.Ito,M.Wada,H.Watanabe,M.Nagai,A.Hayashi,T.Murashima and N.Ono,"Synthesis and structures of pyrroles fused with rigid bicyclic ring systems at β−positions"J.Chem.Soc.,Perkin Trans.1,4347−4355,2001
ビシクロピロールの構造を分子内に1つ有する単量体化合物を用いる場合には、下記一般式(1)で表される化合物を用いることが好ましい。
ビシクロピロールの構造を分子内に2以上有する多量体化合物、すなわち、ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造が2以上分子内に存在する化合物を用いる場合には、下記一般式(2)で表される化合物を用いることが好ましい。
ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物は、超臨界二酸化炭素雰囲気下で保持される。
本発明のイソインドール類の製造方法においては反応工程に先だって、ビシクロピロールの構造を分子内に有する化合物を準備する等必要な前工程を適宜行うことができる。こうした準備工程については、上記各化合物の欄で説明したとおりである。
本発明のイソインドール類は、上記のイソインドール類の製造方法によって製造されたものである。これにより、超臨界二酸化炭素雰囲気を用いることによって、反応系内の脱気が良好に行われるとともに、原料たるビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物が良好に分散・溶解されるので、効率的な熱処理を行うことができ、その結果、相対的に低温での反応となるので工業的に実用化可能な条件を採用することができ、安定なイソインドール類が得られ、さらにイソインドール類を高収率で製造できる、イソインドール類の製造方法によって製造されたイソインドール類を提供することができる。
以下に示す化合物(Ethyl 4,7−dihydro−4,7−ethano−2H−isoindole−1−carboxylate)0.050gを内容積50mlのステンレス製の反応器に導入した。
以下に示す化合物(Ethyl 3−chloro−4,7−dihydro−4,7−ethano−2H−isoindole−1−carboxylate)0.050gを内容積50mlのステンレス製の反応器に導入した。
以下に示す化合物(ビシクロポルフィリン)0.050gを内容積50mlのステンレス製の反応器に導入した。
以下に示す化合物(5,10,15,20−テトラフェニルビシクロポルフィリン)0.050gを内容積50mlのステンレス製の反応器に導入した。なお、下記化合物において、「Ph」はフェニル基を表す。
以下に示す化合物(ビシクロ[2.2.2]オクタジエン環が縮環したピロメテン)0.050gを内容積50mlのステンレス製の反応器に導入した。なお、下記化合物において、「Et」はエチル基を表す。
Claims (7)
- ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物を、超臨界二酸化炭素雰囲気下で保持する熱処理工程を有することを特徴とするイソインドール類の製造方法。
- 前記熱処理工程が50℃以上、300℃以下の温度で行われる、請求項1に記載のイソインドール類の製造方法。
- 前記ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物が、下記一般式(1)で表される、請求項1又は2に記載のイソインドール類の製造方法。
- 前記ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物が、下記一般式(2)で表される、請求項1又は2に記載のイソインドール類の製造方法。
- 前記ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物が、下記一般式(3A)又は下記一般式(3B)で表される、請求項1又は2に記載のイソインドール類の製造方法。
- 前記ビシクロ[2.2.2]オクタジエン骨格が縮環したピロールの構造を分子内に有する化合物が、下記一般式(4)で表される、請求項1又は2に記載のイソインドール類の製造方法。
- 請求項1〜6のいずれか1項に記載のイソインドール類の製造方法によって製造されることを特徴とするイソインドール類。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008020310A JP4812042B2 (ja) | 2008-01-31 | 2008-01-31 | イソインドール類の製造方法 |
EP08871905.9A EP2248802B1 (en) | 2008-01-31 | 2008-12-24 | Method for producing isoindole and isoindole produced by the method for producing isoindole |
PCT/JP2008/073392 WO2009096126A1 (ja) | 2008-01-31 | 2008-12-24 | イソインドール類の製造方法、及びイソインドール類の製造方法によって製造されるイソインドール類 |
CN2008801284709A CN101983189B (zh) | 2008-01-31 | 2008-12-24 | 异吲哚类的制造方法以及利用异吲哚类的制造方法制造的异吲哚类 |
US12/864,618 US8481753B2 (en) | 2008-01-31 | 2008-12-24 | Method for producing isoindole |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008020310A JP4812042B2 (ja) | 2008-01-31 | 2008-01-31 | イソインドール類の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009179607A true JP2009179607A (ja) | 2009-08-13 |
JP4812042B2 JP4812042B2 (ja) | 2011-11-09 |
Family
ID=40912483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008020310A Expired - Fee Related JP4812042B2 (ja) | 2008-01-31 | 2008-01-31 | イソインドール類の製造方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8481753B2 (ja) |
EP (1) | EP2248802B1 (ja) |
JP (1) | JP4812042B2 (ja) |
CN (1) | CN101983189B (ja) |
WO (1) | WO2009096126A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2454417C1 (ru) * | 2011-03-30 | 2012-06-27 | Государственное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" | 5,15-диаминотетрабензопорфиринат цинка |
RU2458928C1 (ru) * | 2011-06-29 | 2012-08-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" | Способ получения мезо-тетрааминотетрабензопорфирината цинка |
US10447573B2 (en) | 2014-07-17 | 2019-10-15 | Sysmex Corporation | Method and system for aggregating diagnostic analyzer related information |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10333371A1 (de) * | 2003-07-23 | 2005-02-10 | Bayer Ag | Fungizide Wirkstoffkombinationen |
-
2008
- 2008-01-31 JP JP2008020310A patent/JP4812042B2/ja not_active Expired - Fee Related
- 2008-12-24 WO PCT/JP2008/073392 patent/WO2009096126A1/ja active Application Filing
- 2008-12-24 CN CN2008801284709A patent/CN101983189B/zh not_active Expired - Fee Related
- 2008-12-24 EP EP08871905.9A patent/EP2248802B1/en not_active Not-in-force
- 2008-12-24 US US12/864,618 patent/US8481753B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP2248802A4 (en) | 2011-06-22 |
JP4812042B2 (ja) | 2011-11-09 |
US20110137024A1 (en) | 2011-06-09 |
CN101983189B (zh) | 2013-08-07 |
EP2248802B1 (en) | 2013-07-31 |
US8481753B2 (en) | 2013-07-09 |
EP2248802A1 (en) | 2010-11-10 |
CN101983189A (zh) | 2011-03-02 |
WO2009096126A1 (ja) | 2009-08-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Jiao et al. | Fused polycyclic aromatic compounds with near infrared absorption and emission | |
Oshima et al. | A Nonaromatic Thiophene‐Fused Heptalene and Its Aromatic Dianion | |
JP4812042B2 (ja) | イソインドール類の製造方法 | |
Li et al. | Synthesis of π-Extended Imidazoles by 1, 3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles | |
JP2015187100A (ja) | 超分子の包接体及び白色発光材料 | |
Shi et al. | Transition metal free decarboxylative fluoroalkylation of N-acrylamides with 3, 3, 3-trifluoro-2, 2-dimethylpropanoic acid (TFDMPA) | |
Lash et al. | Synthesis, structural characterization and reactivity of heteroazuliporphyrins | |
CN104892485B (zh) | 2‑全氟烷基吲哚衍生物及其合成方法 | |
Binh Nguyen et al. | Toward the Synthesis of Sceptrin and Benzosceptrin: Solvent Effect in Stereo‐and Regioselective [2+ 2] Photodimerization and Easy Access to the Fully Substituted Benzobutane | |
Lledo et al. | The Pauson–Khand reaction of medium sized trans-cycloalkenes | |
JP2007112748A (ja) | 塩素置換ポルフィリン化合物及び塩素置換ポルフィリン化合物の製造方法 | |
Chen et al. | Zinc quinolates through styryl substitution in 2-position via acetoxy exchange reaction | |
Butler et al. | Desymmetrization Reactions of Indigo with Grignard Reagents for the Synthesis of Selective Antiplasmodial [1 H, 3′ H]-3-Aryl-2, 2′-diindol-3′-ones | |
Mosslemin et al. | B (HSO 4) 3 as an Efficient Catalyst for the Syntheses of Bis (1H-Indol-3-yl) ethanones and Bis (benzotriazol-1-yl) ethanones | |
Znoiko et al. | Synthesis of lanthanide complexes of phthalocyanines containing both naphthoxy and benzotriazole fragments | |
Chen et al. | Fluoroalkylation of porphyrins: Generation of 2-and 20-perfluoroalkyl-5, 10, 15-triarylporphyrin radicals and their intramolecular cyclizations | |
JP7011242B2 (ja) | ハロゲンコーティングメタセシス触媒及びその方法 | |
Jaung | Synthesis of new porphyrins with dicyanopyrazine moiety and their optical properties | |
CN110724094A (zh) | 一种喹啉类化合物及其合成方法 | |
JPWO2016039262A1 (ja) | フラーレン誘導体の製造方法 | |
JP2019137676A (ja) | ポルフィセン化合物の製造方法 | |
Jiang et al. | Synthesis and reactions of the first fluoroalkylated Ni (II) N-confused porphyrins | |
JP5196463B2 (ja) | モリブデンポルフィセン錯体及び酸化触媒 | |
CN102659825B (zh) | 一种含有硼氮杂五元环荧光化合物的合成方法 | |
Guryev et al. | Light‐Driven Catalyst‐Free Access to Phthalazines: Entry to Antiviral Model Drugs by Merging Domino Reactions |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110125 |
|
A871 | Explanation of circumstances concerning accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A871 Effective date: 20110125 |
|
A975 | Report on accelerated examination |
Free format text: JAPANESE INTERMEDIATE CODE: A971005 Effective date: 20110317 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110412 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110524 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110705 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110708 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110726 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110819 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140902 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |