CN115043770A - 一种吲哚/氮杂吲哚类化合物的光诱导合成方法 - Google Patents
一种吲哚/氮杂吲哚类化合物的光诱导合成方法 Download PDFInfo
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- CN115043770A CN115043770A CN202210873306.2A CN202210873306A CN115043770A CN 115043770 A CN115043770 A CN 115043770A CN 202210873306 A CN202210873306 A CN 202210873306A CN 115043770 A CN115043770 A CN 115043770A
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- indole
- diboron
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000001308 synthesis method Methods 0.000 title claims abstract description 25
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims abstract description 22
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims abstract description 22
- -1 azaindole compound Chemical class 0.000 title claims abstract description 14
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002475 indoles Chemical class 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000010189 synthetic method Methods 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229940117969 neopentyl glycol Drugs 0.000 claims 2
- SCWWDULYYDFWQV-UHFFFAOYSA-N (2-hydroxyphenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1O SCWWDULYYDFWQV-UHFFFAOYSA-N 0.000 claims 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 230000001939 inductive effect Effects 0.000 abstract 1
- 239000003480 eluent Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- DSDBYQDNNWCLHL-UHFFFAOYSA-N 1-(2-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1[N+]([O-])=O DSDBYQDNNWCLHL-UHFFFAOYSA-N 0.000 description 1
- SZSZDBFJCQKTRG-UHFFFAOYSA-N 1h-indole-6-carbonitrile Chemical compound N#CC1=CC=C2C=CNC2=C1 SZSZDBFJCQKTRG-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- SLRIOXRBAPBGEI-UHFFFAOYSA-N 2-(2-nitrophenyl)ethanol Chemical class OCCC1=CC=CC=C1[N+]([O-])=O SLRIOXRBAPBGEI-UHFFFAOYSA-N 0.000 description 1
- ZNJRONVKWRHYBF-UHFFFAOYSA-N 2-[2-[2-(1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1C=CC1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-UHFFFAOYSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- JTDGUEWGCKJFJZ-UHFFFAOYSA-N 4-(2-hydroxyethyl)-3-nitrobenzonitrile Chemical compound OCCC1=CC=C(C#N)C=C1[N+]([O-])=O JTDGUEWGCKJFJZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 238000006783 Fischer indole synthesis reaction Methods 0.000 description 1
- 238000007211 Larock indole synthesis reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- QZEWCQGGAIGUPS-UHFFFAOYSA-N benzene-1,2-diol;boric acid Chemical compound OB(O)O.OC1=CC=CC=C1O.OC1=CC=CC=C1O QZEWCQGGAIGUPS-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Abstract
本发明公开了一种吲哚/氮杂吲哚类化合物的合成方法,取代或非取代的邻硝基芳基/杂芳基乙醇在可见光照下诱导激发,在联硼试剂作用下发生脱氧环化反应,脱氧环化得到吲哚/氮杂吲哚类化合物。本发明所述方法反应条件温和,在室温常压即可完成,几乎对所有官能团具备兼容性,可以用来合成多官能化的吲哚或氮杂吲哚类化合物。
Description
技术领域
本发明属于化学合成领域,具体涉及一种吲哚/氮杂吲哚类化合物的光诱导合成方法,具体为邻硝基芳基/杂芳基乙醇在可见光诱导下,在联硼试剂协同脱氧下环化而成。
背景技术
吲哚骨架是重要的氮杂环化合物,覆盖各个领域包括生物活性分子、上市药物以及材料功能分子等。由于它们的重要性,围绕这两种骨架分子的合成具有100年的悠久历史,至今长久不衰,不断激发更多的科研工作者开发新的合成策略。例如对于吲哚合成早期著名的合成方法包括Fischer吲哚合成、Bischler吲哚合成、Larock吲哚合成。但有很大的局限性,主要体现在有限的底物范围,繁琐的原料制备步骤,苛刻的反应条件以及有毒试剂的使用。并且,这些方法往往面临较差的官能团容忍性以及区域选择性等问题。因此,对于更具有选择性、更直接、更经济并且具有环境友好型的合成方法一直是化学合成界的热点。硝基芳化合物作为一种容易制备且商业化可得的廉价原料,在近几十年来,一直得到了广泛的利用。直接利用硝基芳化物制备氮杂环是一种具有经济效益且符合可持续发展的策略。目前利用硝基芳烃构建氮杂环化合物得到一定发展,通常这些方法过度依赖于外在苛刻条件,包括有毒金属催化剂、超级量还原试剂、强酸强碱以及高温高压条件。无金属无光敏剂参与的可见光诱导硝基芳烃可控性地构建吲哚是一种机遇和挑战。
发明内容
本发明针对现有技术不足,提供了一种吲哚/氮杂吲哚类化合物的合成方法,光诱导下与联硼试剂协同脱氧下环化而成。
本发明具体技术方案如下:
一种吲哚/氮杂吲哚类化合物的合成方法,将取代或非取代的邻硝基芳基/杂芳基乙醇经过可见光诱导激发,在联硼试剂协同脱氧下环化而成,
Ar代表被一个或多个取代基取代苯、萘、菲、吡嗪、哒嗪、苯并呋喃、苯并噻唑、1,2-苯并吡喃酮、吲哚、喹啉、异喹啉;Ar被多个基团取代时,这些基团相同或者不同;
Ar的取代基以及R1、R2相同或不同,选自:H,F,Cl,Br,I,NH2,-CN,-COOH,-CHO,-Bpin,-B(OH)2,C1-C10烷基,C1-C10烷氧基,C2-C10烯基,C3-C10炔基,C2-C10烷硫基,C2-C10烷基甲酰基,C3-C10烷氧羰基,C5-C10氨甲酰基,芳基甲酰基,其中芳基为苯基、萘基、蒽基、吡啶、呋喃、噻吩或吡咯;
或者,被H、F、Cl、Br、I、-CHO、C1-C10烷氧基、C3-C10烷氧羰基、C2-C10烯基、苯基中的一个或多个取代的苯基、噻吩、呋喃、吡咯、吡唑或吡啶。
优选的,Ar为苯、苯并呋喃或吡啶。
Ar为吡啶时,氮杂吲哚包括4-氮杂-、5-氮杂-、6-氮杂-、7-氮杂-吲哚。
优选的,所述Ar的取代基以及R1、R2相同或不同,选自H、F、Cl、Br、I、NH2、-CN、-COOH、-CHO、C1-C10烷基、C2-C10烯基、C3-C10炔基、C1-C10烷氧基,苯乙炔基、环丙烷基、卤代烷基、环己烯基、苯甲醛基、四苯乙烯基、乙酸乙酯基、异丁酰胺基中的一种或几种。
本发明所述的方法,合成条件为光照波长为300-500nm,在联硼试剂和碱(催化量)存在下,有机溶剂中,0℃-80℃,惰性气体保护下反应3-12小时。
优选的,光照波长为400nm。
所述联硼试剂选自双(新戊基乙二醇)二硼(B2nep2)、联硼酸频那醇酯(B2pin2)、双联邻苯二酚硼酸酯(B2cat2)、四羟基二硼(B2(OH)4)中的一种或几种。优选为双(新戊基乙二醇)二硼。
所述碱选自碳酸钾、碳酸钠、碳酸锂、叔丁醇钾、叔丁醇钠、三乙胺、N,N-二异丙基乙胺(DIPEA)中的一种或几种。优选为N,N-二异丙基乙胺。
所述有机溶剂选自二氯甲烷、二氯乙烷、乙腈、甲醇、乙醇、四氢呋喃、二甲基亚砜、N,N-二甲基甲酰胺中的一种或几种。优选为四氢呋喃和甲醇的混合溶剂,体积比为8:1。
具体的示例为:
(1)添加1倍当量取代或非取代2-(2-硝基苯基)乙醇/2-硝基-3-羟乙基吡啶,加入2.2倍当量联硼试剂(双(新戊基乙二醇)二硼),0.2倍当量的有机碱(N,N-二异丙基乙胺)试剂,0.5M四氢呋喃和甲醇的混合溶剂(8:1,v/v)。
(2)在室温下,氮气氛围中,用400nm波长蓝光照射3-12小时,得到吲哚/氮杂吲哚类化合物。
(3)反应结束后,对产物进行分离纯化,如重结晶、柱层析等。
本发明优点:
本发明克服了现有技术的缺陷,在提供了一种简单高效,成本低廉,环境友好条件下制备芳杂环化合物的方法。所述反应在室温常压即可完成,几乎对所有官能团具备兼容性,可以用来合成多官能化的吲哚或氮杂吲哚类化合物,且易于工业产量化。
具体实施方式:
以下通过实施例对本发明的上述内容做进一步详细说明,但不应该将此理解为本发明上述主题的范围仅限于以下的实施例,凡基于本发明上述内容实现的技术均属于本发明的范围。在以下实施例中,未详细描述的各种过程和方法是本领域中公知的常规方法。
实施例1
本实施例以6-氰基吲哚为例(例1-1),考察联硼试剂、碱、溶剂和光照对反应产率的影响。
取一反应管,添加0.2mmol 4-(2-羟乙基)-3-硝基苯甲腈,2.2倍当量联硼试剂,0.2倍当量的碱,有机溶剂0.5mL(0.5M),在氮气氛围中,光照下,室温条件下反应12h,反应结束后,旋干,用石油醚/二氯甲烷=20/1-1/1比例的洗脱剂,硅胶柱层析分离,计算产率。
1H NMR(400MHz,CDCl3):δ8.78(br,s,1H,NH),7.77(d,J=1.4Hz,1H),7.70(d,J=8.2Hz,1H),7.45–7.41(m,1H),7.35(dd,J=8.2,1.4Hz,1H),6.63(m,1H).13C NMR(100MHz,CDCl3):δ134.72,131.31,128.30,122.76,121.64,120.92,116.18,104.21,103.48.HRMS(ESI+)of 2f:m/z calcd for C9H6N2[M+H]+:143.06092,Found:143.06040。
通过改变反应的碱、联硼试剂、溶剂、光照反应条件,得到一系列的结果,如下表:
上述结果表明,合成吲哚条件中,N,N-二甲基甲酰胺(DIPEA)、双(新戊基乙二醇)二硼(B2nep2)、四氢呋喃/甲醇=8/1、400nm为反应最优条件。
实施例2考察本发明所述方法对不同吲哚分子合成的适应性
吲哚合成通用方法:取一反应管,添加0.2mmol邻硝基苯乙醇类底物,2.2倍当量双(新戊基乙二醇)二硼,0.2倍当量N,N-二异丙基乙胺,溶剂体积比为8/1的四氢呋喃/甲醇0.5mL(0.5M)为反应溶剂,在氮气氛围中,400nm光照下,室温条件下反应12h,反应结束后,旋干,用石油醚/二氯甲烷=20/1-1/1比例的洗脱剂,硅胶柱层析分离,计算产率。
例1-2:
合成方法参照吲哚合成通用方法:硝基芳香物(53mg,0.2mmol),B2nep2(99mg,0.44mmol),3:1比例的PE/DCM作为洗脱剂,得到分离产率为78%的棕色固体。
1H NMR(400MHz,CDCl3):δ8.24(br,s,1H,NH),7.62(m,2H),7.44–7.32(m,5H),7.28(t,J=2.8Hz,1H),7.19(t,J=7.7Hz,1H),6.83(s,1H).13C NMR(100MHz,CDCl3):δ135.54,131.78,129.52,128.47,128.17,124.89,123.91,122.01,115.01,111.78,102.61,91.92,88.51,88.51.HRMS(ESI+)of 2i:m/z calcd for C16H11N[M+H]+:218.09595,Found:218.09643。
例1-3:
合成方法参照吲哚合成通用方法:硝基芳香物(45mg,0.2mmol),B2nep2(99mg,0.44mmol),5:1比例的PE/DCM作为洗脱剂,得到分离产率为92%的白色固体。
1H NMR(400MHz,CDCl3):δ8.08(br,s,1H,NH),7.28(d,J=8.5Hz,1H),7.18(dd,J=3.1,2.5Hz,1H),7.13(d,J=2.5Hz,1H),6.88(dd,J=8.5,2.5Hz,1H),6.50(ddd,J=3.1,2.1,1.0Hz,1H),3.87(s,3H).13C NMR(100MHz,CDCl3):δ154.29,131.08,128.40,125.00,112.46,111.83,102.48,102.45,55.99.HRMS(ESI+)of 2k:m/z calcd for C9H9NO[M+H]+:148.0757,Found:148.0757。
例1-4:
合成方法参照吲哚合成通用方法:硝基芳香物(49mg,0.2mmol),B2nep2(99mg,0.44mmol),1:1比例的PE/DCM作为洗脱剂,得到分离产率为48%的棕色固体。
1H NMR(400MHz,DMSO-d6):δ8.60(s,1H),8.17(s,1H),7.45(d,J=3.1Hz,1H),6.55(d,J=3.0Hz,1H).13C NMR(100MHz,DMSO-d6):δ137.94,134.05,133.24,132.40,130.06,112.56,101.89.HRMS(ESI+)of 2m:m/z calcd for C7H5N2Br[M+H]+:196.9709,Found:196.9709。
例1-5:
合成方法参照吲哚合成通用方法:硝基芳香物(41mg,0.2mmol),B2(OH)4(40mg,0.44mol),10:1比例的PE/DCM作为洗脱剂,得到分离产率为95%的淡黄色固体。
1H NMR(400MHz,CDCl3):δ7.91(br,s,1H,NH),7.52(dd,J=7.8,1.0Hz,1H),7.28(dd,J=8.1,1.0Hz,1H),7.13(ddd,J=7.8,7.8,1.4Hz,1H),7.08(ddd,J=7.4,7.8,1.3Hz,1H),6.17(s,1H),1.97(m,1H),1.01–0.95(m,2H),0.83–0.74(m,2H).13C NMR(100MHz,CDCl3):δ141.82,135.87,128.84,121.13,119.86,119.81,110.32,97.87,9.00,7.44.HRMS(ESI+)of 2o:m/z calcd for C11H11N[M+H]+:158.0964,Found:158.0952。
例1-6:
合成方法参照吲哚合成通用方法:硝基芳香物(49mg,0.2mmol),B2(OH)4(40mg,0.44mol),10:1比例的PE/DCM作为洗脱剂,得到分离产率为94%的无色油状物。
1H NMR(400MHz,CDCl3):δ7.94(br,s,1H,NH),7.58(dd,J=7.5,1.2Hz,1H),7.33(dd,J=7.4,1.1Hz,1H),7.16(ddd,J=7.5,7.4,1.3Hz,1H),7.11(ddd,J=7.5,7.4,1.1Hz,1H),6.30(s,1H),5.83(m,2H),2.55–1.73(m,7H).13C NMR(100MHz,CDCl3):δ144.42,135.76,128.68,127.39,126.07,121.18,120.04,119.74,110.52,98.12,33.30,31.44,28.86,25.09.HRMS(ESI+)of 2p:m/z calcd for C14H15N[M+H]+:198.1275,Found:198.1277。
例1-7:
合成方法参照吲哚合成通用方法:硝基芳香物(54mg,0.2mmol),B2(OH)4(40mg,0.44mol),20:1比例的PE/DCM作为洗脱剂,得到分离产率为98%的黄色固体。
1H NMR(400MHz,DMSO-d6):δ11.75(br,s,1H,NH),10.01(br,s,1H,CHO),8.09(d,J=8.1Hz,2H),7.98(d,J=8.1Hz,2H),7.58(d,J=7.9Hz,1H),7.44(d,J=8.1Hz,1H),7.15(dd,J=7.9,7.9Hz,2H),7.14(s,1H),7.03(dd,J=7.4,7.4Hz,1H).13C NMR(100MHz,DMSO-d6):δ192.28,137.74,137.71,136.10,134.67,130.25,128.42,125.19,122.66,120.60,119.77,111.59,101.46.HRMS(ESI+)of 2t:m/z calcd for C15H11NO[M+H]+:222.09134,Found:222.09037。
例1-8:
合成方法参照吲哚合成通用方法:硝基芳香物(99mg,0.2mmol),B2(OH)4(40mg,0.44mol),5:1比例的PE/DCM作为洗脱剂,得到分离产率为62%的黄色固体。
1H NMR(400MHz,DMSO-d6):δ11.43(br,s,1H,NH),7.62(d,J=8.2Hz,2H),7.49(d,J=7.8Hz,1H),7.35(d,J=8.1Hz,1H),7.22–6.93(m,20H),6.83(d,J=2.0Hz,1H).13C NMR(100MHz,DMSO-d6):δ143.23,143.17,143.04,142.18,140.73,140.14,137.21,137.13,131.21,130.76,130.68,130.65,130.24,128.58,127.93,127.87,127.80,126.66,126.63,126.54,124.31,121.57,119.97,119.34,111.20,98.79.HRMS(ESI+)of 2y:m/z calcd forC34H25N[M+H]+:448.2084,Found:448.2060。
例1-9:
合成方法参照吲哚合成通用方法:硝基芳香物(77mg,0.2mmol),B2(OH)4(40mg,0.44mol),5:1比例的PE/DCM作为洗脱剂,得到分离产率为92%的棕色固体。
1H NMR(400MHz,DMSO-d6):δ11.87(br,s,1H,NH),7.97(s,1H),7.56(d,J=8.9Hz,1H),7.51(s,2H),7.42(d,J=8.9Hz,1H),7.20(d,J=2.1Hz,1H),6.97(s,1H),4.37(q,J=7.1Hz,2H),2.35(s,6H),1.36(t,J=7.1Hz,3H).13C NMR(100MHz,DMSO-d6):δ158.83,151.44,143.68,138.53,137.95,133.10,131.83,129.06,122.79,121.47,118.35,113.53,112.76,105.70,97.99,60.82,21.02,14.22.HRMS(ESI+)of 2z:m/z calcd for C21H19NO3[M+H]+:334.14377,Found:334.13531。
例1-10:
合成方法参照吲哚合成通用方法:硝基芳香物(95mg,0.2mmol),B2nep2(99mg,0.44mol),2:1比例的PE/DCM作为洗脱剂,得到分离产率为78%的淡黄色固体。
1H NMR(400MHz,DMSO-d6):δ11.37(br,s,1H,NH),9.91(br,s,1H,NH),8.12(d,J=2.0Hz,1H),7.94(d,J=8.3Hz,2H),7.75(d,J=2.0Hz,1H),7.66(d,J=8.3Hz,2H),7.07(d,J=2.0Hz,1H),2.60(hept,J=6.8Hz,1H),1.13(d,J=6.8Hz,6H).13C NMR(100MHz,DMSO-d6):δ175.05,139.61,131.68,131.52,130.60,128.61,128.27,126.37,124.18(q,J=272.4Hz),121.16,114.41,112.40(q,J=5.5Hz),112.03(q,J=32.0Hz),100.84,34.95,19.53.19F NMR(376MHz,DMSO-d6):δ-59.79.HRMS(ESI+):m/z calcd for C19H16F3BrN2O[M+H]+:425.04709,Found:425.04620。
Claims (9)
1.一种吲哚/氮杂吲哚类化合物的合成方法,其特征在于取代或非取代的邻硝基芳基/杂芳基乙醇在可见光照下诱导激发,在联硼试剂作用下发生脱氧环化反应,脱氧环化得到吲哚/氮杂吲哚类化合物,
Ar代表被一个或多个取代基取代苯、萘、菲、吡嗪、哒嗪、苯并呋喃、苯并噻唑、1,2-苯并吡喃酮、吲哚、喹啉、异喹啉;Ar被多个基团取代时,这些基团相同或者不同;
Ar的取代基以及R1、R2相同或不同,选自:
H,F,Cl,Br,I,NH2,-CN,-COOH,-CHO,-Bpin,-B(OH)2,C1-C10烷基,C1-C10烷氧基,C2-C10烯基,C3-C10炔基,C2-C10烷硫基,C2-C10烷基甲酰基,C3-C10烷氧羰基,C5-C10氨甲酰基,芳基甲酰基,其中芳基为苯基、萘基、蒽基、吡啶、呋喃、噻吩或吡咯;
或者,被H、F、Cl、Br、I、-CHO、C1-C10烷氧基、C3-C10烷氧羰基、C2-C10烯基、苯基中的一个或多个取代的苯基、噻吩、呋喃、吡咯、吡唑或吡啶。
2.根据权利要求1所述的合成方法,其特征在于Ar的取代基以及R1、R2相同或不同选自H、F、Cl、Br、I、NH2、-CN、-COOH、-CHO、C1-C10烷基、C2-C10烯基、C3-C10炔基、C1-C10烷氧基,苯乙炔基、环丙烷基、卤代烷基、环己烯基、苯甲醛基、四苯乙烯基、乙酸乙酯基、异丁酰胺基中的一种或几种。
3.根据权利要求1所述的合成方法,其特征在于合成条件为光照波长为300-500nm,在联硼试剂和碱存在下,有机溶剂中,0℃-80℃,惰性气体保护下反应3-12小时。
4.根据权利要求3所述的合成方法,其特征在于光照波长为400nm。
5.根据权利要求3所述的合成方法,其特征在于所述联硼试剂选自双(新戊基乙二醇)二硼、联硼酸频那醇酯、双联邻苯二酚硼酸酯、四羟基二硼中的一种或几种。
6.根据权利要求3所述的合成方法,其特征在于所述碱选自碳酸钾、碳酸钠、碳酸锂、叔丁醇钾、叔丁醇钠、三乙胺、N,N-二异丙基乙胺中的一种或几种。
7.根据权利要求3所述的合成方法,其特征在于所述溶剂选自二氯甲烷、二氯乙烷、乙腈、甲醇、乙醇、四氢呋喃、二甲基亚砜、N,N-二甲基甲酰胺中的一种或几种。
8.根据权利要求7所述的合成方法,其特征在于所述溶剂为四氢呋喃和甲醇的混合溶剂,体积比为8:1。
9.根据权利要求8所述的合成方法,其特征在于所述联硼试剂为双(新戊基乙二醇)二硼,碱为N,N-二异丙基乙胺,反应温度为25℃。
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