PH27153A - Benzopyran derivatives - Google Patents

Info

Publication number

PH27153A

PH27153A PH37176A PH37176A PH27153A PH 27153 A PH27153 A PH 27153A PH 37176 A PH37176 A PH 37176A PH 37176 A PH37176 A PH 37176A PH 27153 A PH27153 A PH 27153A

Authority

PH

Philippines

Prior art keywords

benzopyran

oxide

dimethyl

dihydro

pyridine

Prior art date

1987-07-06

Links

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• 150000001562 benzopyrans Chemical class 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 160
• -1 nitrobenzoyl Chemical group 0.000 claims description 74
• ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 63
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 239000001257 hydrogen Substances 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 238000000034 method Methods 0.000 claims description 34
• 150000001204 N-oxides Chemical class 0.000 claims description 32
• 239000002253 acid Substances 0.000 claims description 22
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000000815 N-oxide group Chemical group 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 150000002431 hydrogen Chemical group 0.000 claims description 12
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000001589 carboacyl group Chemical group 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 206010002383 Angina Pectoris Diseases 0.000 claims description 6
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
• 206010019280 Heart failures Diseases 0.000 claims description 6
• 206010020772 Hypertension Diseases 0.000 claims description 6
• 208000029578 Muscle disease Diseases 0.000 claims description 6
• 208000021642 Muscular disease Diseases 0.000 claims description 6
• 230000002490 cerebral effect Effects 0.000 claims description 6
• 230000002093 peripheral effect Effects 0.000 claims description 6
• 210000002460 smooth muscle Anatomy 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 208000019553 vascular disease Diseases 0.000 claims description 6
• OOKJTGMLXKUVOW-UHFFFAOYSA-N 2,2-dimethyl-4-pyrimidin-2-yl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=NC=CC=N1 OOKJTGMLXKUVOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• VJFKERVNQSGERR-UHFFFAOYSA-N 2,2-dimethyl-4-(4-methyl-1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound CC1=CC=[N+]([O-])C(C=2C3=CC(=CC=C3OC(C)(C)C=2)C#N)=C1 VJFKERVNQSGERR-UHFFFAOYSA-N 0.000 claims description 3
• VBUWHWHLKQVZNI-UHFFFAOYSA-N 2,2-dimethyl-4-pyrazin-2-yl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CN=CC=N1 VBUWHWHLKQVZNI-UHFFFAOYSA-N 0.000 claims description 3
• DVOHDQNIFVLXOL-UHFFFAOYSA-N 2-(2,2-dimethyl-6-methylsulfanyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(SC)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] DVOHDQNIFVLXOL-UHFFFAOYSA-N 0.000 claims description 3
• YNTSDNKWTDAYAT-UHFFFAOYSA-N 4-(2,2-dimethylchromen-4-yl)pyridin-3-ol Chemical compound C=1C(C)(C)OC2=CC=CC=C2C=1C1=CC=NC=C1O YNTSDNKWTDAYAT-UHFFFAOYSA-N 0.000 claims description 3
• JDLRFGAYBSYNSO-UHFFFAOYSA-N 4-(5-hydroxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=C(O)C=[N+]1[O-] JDLRFGAYBSYNSO-UHFFFAOYSA-N 0.000 claims description 3
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• KIIGVFITJOATPV-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 KIIGVFITJOATPV-UHFFFAOYSA-N 0.000 claims description 2
• PQVILGHAVGQHRP-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] PQVILGHAVGQHRP-UHFFFAOYSA-N 0.000 claims description 2
• SQPQBCKNVMBCEE-UHFFFAOYSA-N 2,2-dimethyl-4-[5-(4-methylphenyl)-1-oxidopyridin-1-ium-2-yl]chromene-6-carbonitrile Chemical compound C1=CC(C)=CC=C1C(C=[N+]1[O-])=CC=C1C1=CC(C)(C)OC2=CC=C(C#N)C=C12 SQPQBCKNVMBCEE-UHFFFAOYSA-N 0.000 claims description 2
• SDUIPMRMROTXEI-UHFFFAOYSA-N 2-(2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC([N+]([O-])=O)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] SDUIPMRMROTXEI-UHFFFAOYSA-N 0.000 claims description 2
• VZONCHQVBLCHLM-UHFFFAOYSA-N 2-(6-bromo-2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(Br)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] VZONCHQVBLCHLM-UHFFFAOYSA-N 0.000 claims description 2
• AYRYWZHUJGNCCF-UHFFFAOYSA-N 2-(6-bromo-2,2-dimethylchromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C=1C(C)(C)OC2=CC=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] AYRYWZHUJGNCCF-UHFFFAOYSA-N 0.000 claims description 2
• IZVIEWXJZOFDHI-UHFFFAOYSA-N 4-(5-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=C(Cl)C=[N+]1[O-] IZVIEWXJZOFDHI-UHFFFAOYSA-N 0.000 claims description 2
• HJCWJPIYOSBUJJ-UHFFFAOYSA-N 4-(5-cyano-2-hydroxyphenyl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC(C#N)=CC=C1O HJCWJPIYOSBUJJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims 2
• WZFNSLZNUQFRHC-UHFFFAOYSA-N 1-[2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromen-6-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2OC(C)(C)C=C1C1=CC=CC=[N+]1[O-] WZFNSLZNUQFRHC-UHFFFAOYSA-N 0.000 claims 1
• KZNFWTUXXSJNNN-UHFFFAOYSA-N 1-[2-methyl-4-(1-oxidopyridin-1-ium-2-yl)-2h-chromen-6-yl]ethanone Chemical compound C=1C(C)OC2=CC=C(C(C)=O)C=C2C=1C1=CC=CC=[N+]1[O-] KZNFWTUXXSJNNN-UHFFFAOYSA-N 0.000 claims 1
• ZLHVCYUISHRODZ-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 ZLHVCYUISHRODZ-UHFFFAOYSA-N 0.000 claims 1
• BQEBAKFDIRCXSI-UHFFFAOYSA-N 2,2-dimethyl-4-(5-methyl-1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound [O-][N+]1=CC(C)=CC=C1C1C2=CC(C#N)=CC=C2OC(C)(C)C1 BQEBAKFDIRCXSI-UHFFFAOYSA-N 0.000 claims 1
• NYWWLAGHUMTSBB-UHFFFAOYSA-N 2-methoxy-1-oxidopyridin-1-ium Chemical compound COC1=CC=CC=[N+]1[O-] NYWWLAGHUMTSBB-UHFFFAOYSA-N 0.000 claims 1
• KHCVUHPZYJUXLC-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=C1O KHCVUHPZYJUXLC-UHFFFAOYSA-N 0.000 claims 1
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
• YRSPCPACGOAQTP-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-phenylmethanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=CC=C1 YRSPCPACGOAQTP-UHFFFAOYSA-N 0.000 claims 1
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
• 125000003373 pyrazinyl group Chemical group 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 125000005493 quinolyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 516
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 252
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 194
• 239000000243 solution Substances 0.000 description 173
• 239000000203 mixture Substances 0.000 description 154
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 153
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
• 238000002844 melting Methods 0.000 description 99
• 230000008018 melting Effects 0.000 description 99
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 91
• 238000010828 elution Methods 0.000 description 91
• 239000000741 silica gel Substances 0.000 description 87
• 229910002027 silica gel Inorganic materials 0.000 description 87
• 229910052938 sodium sulfate Inorganic materials 0.000 description 77
• 235000011152 sodium sulphate Nutrition 0.000 description 77
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 74
• 239000007858 starting material Substances 0.000 description 71
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
• 239000012074 organic phase Substances 0.000 description 66
• 239000003208 petroleum Substances 0.000 description 59
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 55
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 239000007787 solid Substances 0.000 description 46
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 39
• 235000017557 sodium bicarbonate Nutrition 0.000 description 37
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 229960001407 sodium bicarbonate Drugs 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
• 238000010992 reflux Methods 0.000 description 32
• 238000003756 stirring Methods 0.000 description 32
• 239000003921 oil Substances 0.000 description 30
• 235000019198 oils Nutrition 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
• 238000001953 recrystallisation Methods 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
• 239000003960 organic solvent Substances 0.000 description 24
• 239000002904 solvent Substances 0.000 description 24
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 23
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
• 238000001704 evaporation Methods 0.000 description 21
• 230000008020 evaporation Effects 0.000 description 21
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 20
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
• 239000004289 sodium hydrogen sulphite Substances 0.000 description 20
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 20
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 17
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
• 229960004592 isopropanol Drugs 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• 230000008569 process Effects 0.000 description 16
• 239000011780 sodium chloride Substances 0.000 description 16
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 239000000284 extract Substances 0.000 description 14
• 238000004519 manufacturing process Methods 0.000 description 14
• 239000000706 filtrate Substances 0.000 description 13
• 230000003647 oxidation Effects 0.000 description 13
• 238000007254 oxidation reaction Methods 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 12
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
• 239000012299 nitrogen atmosphere Substances 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
• 229910052783 alkali metal Inorganic materials 0.000 description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• NXUSMKWUASVPPO-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-4-yl)pyridine Chemical compound C12=CC=CC=C2OC(C)(C)CC1C1=CC=CC=N1 NXUSMKWUASVPPO-UHFFFAOYSA-N 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• 239000008346 aqueous phase Substances 0.000 description 9
• 125000003118 aryl group Chemical group 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• 235000011167 hydrochloric acid Nutrition 0.000 description 9
• 229960000443 hydrochloric acid Drugs 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
• 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 8
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 8
• 235000019253 formic acid Nutrition 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
• 150000001340 alkali metals Chemical class 0.000 description 7
• 229960001701 chloroform Drugs 0.000 description 7
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• BJBUSSBIFHSXBR-UHFFFAOYSA-N 4-(2-methylbut-3-yn-2-yloxy)benzonitrile Chemical compound C#CC(C)(C)OC1=CC=C(C#N)C=C1 BJBUSSBIFHSXBR-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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