CN112625039B - 吡咯并喹啉类化合物及其合成方法 - Google Patents
吡咯并喹啉类化合物及其合成方法 Download PDFInfo
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- CN112625039B CN112625039B CN202110058137.2A CN202110058137A CN112625039B CN 112625039 B CN112625039 B CN 112625039B CN 202110058137 A CN202110058137 A CN 202110058137A CN 112625039 B CN112625039 B CN 112625039B
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- pyrroloquinoline
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- -1 Pyrroloquinoline compound Chemical class 0.000 title claims abstract description 43
- 238000001308 synthesis method Methods 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 7h-pyrrolo[2,3-h]quinoline Chemical compound C1=CN=C2C(C=CN3)=C3C=CC2=C1 ZIUYHTQZEPDUCZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 8
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 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
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- SLHCMPVPVQSTBV-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=C1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=C1 SLHCMPVPVQSTBV-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 4
- 238000005580 one pot reaction Methods 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000008204 material by function Substances 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 238000005215 recombination Methods 0.000 abstract description 2
- 230000006798 recombination Effects 0.000 abstract description 2
- 229910052723 transition metal Inorganic materials 0.000 abstract description 2
- 150000003624 transition metals Chemical class 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 76
- 239000000047 product Substances 0.000 description 23
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- WZTMONNZXFLNKU-UHFFFAOYSA-N C1CC(CCC1)=O.N1C=CC2=CC=CC=C12 Chemical class C1CC(CCC1)=O.N1C=CC2=CC=CC=C12 WZTMONNZXFLNKU-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- VLVLNNQMURDGPM-UHFFFAOYSA-N (2,6-dichlorophenyl)methanamine Chemical compound NCC1=C(Cl)C=CC=C1Cl VLVLNNQMURDGPM-UHFFFAOYSA-N 0.000 description 1
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 description 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- ADZUEEUKBYCSEY-UHFFFAOYSA-N 1h-indole-5-carbaldehyde Chemical compound O=CC1=CC=C2NC=CC2=C1 ADZUEEUKBYCSEY-UHFFFAOYSA-N 0.000 description 1
- CXOPVSYLDOGGIK-UHFFFAOYSA-N 2-(5-methyl-1h-indol-3-yl)cyclohexan-1-one Chemical compound C12=CC(C)=CC=C2NC=C1C1CCCCC1=O CXOPVSYLDOGGIK-UHFFFAOYSA-N 0.000 description 1
- NWYYWIJOWOLJNR-UHFFFAOYSA-N 2-Amino-3-methyl-1-butanol Chemical compound CC(C)C(N)CO NWYYWIJOWOLJNR-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- 102000012440 Acetylcholinesterase Human genes 0.000 description 1
- 108010022752 Acetylcholinesterase Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- YNWLLGBBGKSZDX-UHFFFAOYSA-N CC1=C2NC=C(C(CCCC3)C3=O)C2=CC=C1 Chemical compound CC1=C2NC=C(C(CCCC3)C3=O)C2=CC=C1 YNWLLGBBGKSZDX-UHFFFAOYSA-N 0.000 description 1
- BCLKMDOVZNLFOA-UHFFFAOYSA-N O=C(CCCC1)C1C1=CNC2=CC(Cl)=CC=C12 Chemical compound O=C(CCCC1)C1C1=CNC2=CC(Cl)=CC=C12 BCLKMDOVZNLFOA-UHFFFAOYSA-N 0.000 description 1
- LVGYRYUSSBRAJH-UHFFFAOYSA-N O=C(CCCC1)C1C1=CNC2=CC=CC(Cl)=C12 Chemical compound O=C(CCCC1)C1C1=CNC2=CC=CC(Cl)=C12 LVGYRYUSSBRAJH-UHFFFAOYSA-N 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 241000223109 Trypanosoma cruzi Species 0.000 description 1
- DBGROTRFYBSUTR-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=C(OC(F)(F)F)C=C1 DBGROTRFYBSUTR-UHFFFAOYSA-N 0.000 description 1
- 229940022698 acetylcholinesterase Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
Abstract
本发明主要涉及一种吡咯并喹啉及其衍生物的合成方法。本发明在催化剂和碱的作用下，空气氛围中，实现3‑环己酮基吲哚类化合物、胺类化合物和醛类化合物一锅反应，经历吲哚C‑N键断裂及重组，高选择性得到一种吡咯并喹啉及其衍生物的技术方案。制得结构稳定，化学性质优良的产品及其附加产品，该方法中无需过渡金属催化,为吡咯并喹啉类化合物的合成提供了一条新的路径。具有反应体系简单、反应条件温和、反应设备较少、实验操作简便、用料来源广泛、底物适用性广、原子经济性好、产率优秀等特点。本发明的吡咯并喹啉衍生物及其合成方法，可用于医药、农药、有机功能材料等多个工业生产领域；特别适合一锅法高效选择性合成吡咯并喹啉类化合物的科学研究与开发利用。
Description
技术领域
本发明涉及一种吡咯并喹啉类化合物及其合成方法，属于有机合成领域。
背景技术
吡咯并喹啉类化合物是一类重要的含氮杂环化合物，广泛的存在于天然产物中，吡咯并喹啉类结构也广泛存在于药物分子中，因其具有重要的生物活性，被广泛的应用于医药等方面。如从海洋滑行细菌中分离得到的Marinoquinolines A-F(MQ A-F)被证明具有良好的乙酰胆碱酯酶抑制活性、抗菌、抗真菌、抗恶性疟原虫和抗克氏锥虫等活性。吡咯并喹啉类化合物的合成通常需要高度功能化的原料、过渡金属催化剂、多步反应以及苛刻的反应条件等。
发明内容
因此，本发明的目的是提供一种吡咯并喹啉及其衍生物。
本发明的又一目的是提供一种吡咯并喹啉及其衍生物的合成方法，具有反应条件简单，操作方便、产率高的优点。
从而，本发明的一种吡咯并喹啉及其衍生物，它的通式为式Ⅰ：
其中
R1选自氢原子、烷基，卤素基。
R2选自氢原子、芳基甲基、芳基乙基、杂环芳基甲基、烷基、环烷基、芳基、杂环芳基；具有羟基取代基、二甲氨基取代基、杂环取代基的烷基；
R3选自氢原子、芳基、杂环芳基、烷基、环烷基；
本发明还提供一种合成权利要求1所述的吡咯并喹啉及其衍生物的方法，将3-环己酮基吲哚类化合物、胺类化合物和醛类化合物三组分在催化剂、碱、有机溶剂的反应条件下经加热搅拌得到。
优选的，本发明的方法，所述3-环己酮基吲哚类化合物的通式为式Ⅱ：
其中：
R1选自氢原子、烷基，卤素基。
优选的，本发明的方法，所述3-环己酮基吲哚类化合物选自：4-氯-3-环己酮基吲哚、5-氯-3-环己酮基吲哚、5-甲基-3-环己酮基吲哚、6-氯-3-环己酮基吲哚、7-甲基-3-环己酮基吲哚。
优选的，本发明的方法，所述胺类化合物的通式为Ⅲ：
R2-NH2
Ⅲ
其中：
R2选自氢原子、芳基甲基、芳基乙基、杂环芳基甲基、芳基、杂环芳基、烷基、环烷基；具有羟基取代基、二甲氨基取代基、杂环取代基的烷基。
优选的，本发明的方法，所述胺类化合物选自：苄胺、4-甲基苄胺、4-氯苄胺、4-甲氧基苄胺、4-三氟甲氧基苄胺、3-甲基苄胺、3-氯苄胺、2-甲基苄胺、2-氯苄胺、2，6-二氯苄胺、苯乙胺、α-甲基苄胺、4-氨甲基吡啶、2-甲氨基吡啶、2-噻吩甲胺、苯胺、4-甲基苯胺、4-氯苯胺、2-萘胺、对苯二胺、1,5-萘二胺、3氨基苄胺、8-氨基喹啉、甲胺盐酸盐、正己胺、仲丁胺、环己胺、乙醇胺、己醇胺、缬氨醇、3-二甲氨基-1-丙胺、N-(3-氨丙基)吗啉、N-氨基吗啉。
优选的，本发明的方法，所述醛类化合物的通式为式Ⅳ：
R3-CHO
Ⅳ
其中：
R3选自氢原子、芳基、杂环芳基、烷基、环烷基。
优选的，本发明的方法，所述醛类化合物选自：2-萘甲醛、2-噻吩甲醛、2-吡咯甲醛、3-吲哚甲醛、5-吲哚甲醛、正辛醛、环己醛、叔丁醛、2-苯基丙醛、水杨醛、香草醛、藜芦醛。
优选的，本发明的方法，所述催化剂为：NH4I、单质碘、KI、NIS、IBr、I2O5、NaIO4中的一种。
优选的，本发明的方法，所述碱为：NaHCO3、Na2CO3、Li2CO3、KHCO3、K2HPO4、醋酸钠、吡啶、吗啉、三乙胺中的一种。
优选的，本发明的方法，所述有机溶剂选自氯苯、甲苯、三氟甲苯、对二甲苯、1,4-二氧六环、乙腈、环己烷、吡啶、乙基苯、苯甲醚中的一种，所述溶剂的用量为：0-1.0mL。
优选的，本发明的方法，所述3-环己酮基吲哚类化合物、胺类化合物、醛类化合物、催化剂、碱的摩尔比为1.0：1.0-2.0:1.0-2.0:0.05-0.5:0-4.0；反应温度为130℃-160℃；反应容器的气氛为：空气或氧气氛围；反应时长为2h-16h。
本发明技术方案，具有如下优点：
(I)本发明在催化剂和碱的作用下，空气氛围中，实现3-环己酮基吲哚类化合物、胺类化合物和醛类化合物一锅反应，经历吲哚C-N键断裂及重组，高选择性得到一种吡咯并喹啉及其衍生物的技术方案，一步直接选择性的合成目标产物，克服了现有多步合成，需要用金属催化剂的方法带来的人、财、物的巨大浪费问题，节约了大量的研究时间与缩短生产周期；(II)3-环己酮基吲哚类化合物、胺类化合物和醛类化合物三组分在催化剂、碱、有机溶剂的反应条件下经加热搅拌选择性得到一种吡咯并喹啉及其衍生物的技术方案，它具有反应体系简单，反应条件温和，用料来源广泛，产品附加值增加显著且可利用性高，具备可预见的市场商业化前景；(III)3-环己酮基吲哚类化合物、胺类化合物和醛类化合物三组分转化为吡咯并喹啉及其衍生物的技术方案，它工艺科学、合理，基团定位和选择性好，用料来源广泛，原子经济性好，结构稳定，实验操作容易，反应步骤明显缩短，所需仪器设备少；(IV)本发明的吡咯并喹啉衍生物及其合成方法，可用于医药、农药、有机功能材料等多个工业生产领域；特别适合一锅法高效选择性合成吡咯并喹啉类化合物的科学研究与开发利用。
具体实施方式
现在结合附图对本发明作进一步详细的说明。这些附图均为简化的示意图，仅以示意方式说明本发明的基本结构，因此其仅显示与本发明有关的构成。
实施例1-19
包括以下步骤：
⑴在反应容器中加入3-环己酮基吲哚类化合物、胺类化合物、醛类化合物、催化剂、碱和有机溶剂；
⑵将反应物充分混合后，进行加热；
⑶反应后进行纯化得到产物；
3-环己酮基吲哚类化合物、胺类化合物、醛类化合物、反应条件、反应产物及产率见表1所示。
表1：实施例1-19中的反应物及反应条件。
部分实施例的产物的核磁数据为：
实施例1产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.41(d,J＝7.1Hz,1H),8.18(d,J＝9.4Hz,1H),7.63–7.52(m,2H),7.22(d,J＝8.5Hz,2H),7.11(d,J＝7.0Hz,3H),6.79(d,J＝8.5Hz,2H),6.38(d,J＝6.5Hz,2H),5.01(s,2H),3.83(s,3H),3.26(t,J＝5.9Hz,2H),2.64(t,J＝5.9Hz,2H),2.00–1.93(m,4H).13C NMR(100MHz,CDCl3,ppm)δ159.6,147.5,142.4,139.6,138.2,132.6,130.0,129.5,128.3,127.7,127.7,126.8,125.5,125.1,125.1,123.8,123.3,113.4,112.8,55.4,47.7,24.0,23.3,22.7,22.5.
实施例2产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.30(d,J＝8.8Hz,1H),8.18(s,1H),7.49(d,J＝10.5Hz,1H),7.21(d,J＝8.4Hz,2H),7.12(q,J＝5.4Hz,3H),6.80(d,J＝8.4Hz,2H),6.39(d,J＝6.6Hz,2H),5.01(s,2H),3.83(s,3H),3.20(t,J＝5.9Hz,2H),2.64(t,J＝5.9Hz,2H),2.01–1.91(m,4H).13C NMR(100MHz,CDCl3,ppm)δ159.7,148.3,142.9,140.3,137.9,132.1,130.9,129.9,128.4,128.3,127.7,127.5,126.9,125.7,125.0,124.5,122.1,113.5,112.7,55.4,47.7,23.9,23.2,22.7,22.4.
实施例3产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.39(d,J＝9.5Hz,1H),8.18(d,J＝9.5Hz,1H),7.62–7.51(m,2H),7.22(d,J＝8.6Hz,2H),7.07(d,J＝8.5Hz,2H),6.81(d,J＝8.6Hz,2H),6.29(d,J＝8.5Hz,2H),4.96(s,2H),3.83(s,3H),3.24(t,J＝5.9Hz,2H),2.60(t,J＝5.8Hz,2H),1.98–1.92(m,4H).13C NMR(100MHz,CDCl3,ppm)δ159.7,147.3,142.4,139.3,136.8,132.6,132.5,130.0,129.5,128.4,127.8,127.6,126.4,125.6,125.2,123.8,123.2,113.5,113.0,55.4,47.1,24.0,23.3,22.7,22.5.
实施例4产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.38(d,J＝8.0Hz,1H),8.24(d,J＝7.8Hz,1H),7.63(d,J＝8.5Hz,2H),7.57(t,J＝8.4Hz,2H),7.18–7.11(m,3H),7.08(d,J＝8.5Hz,2H),6.65–6.53(m,2H),4.01(t,J＝7.8Hz,2H),3.92(s,3H),3.20(t,J＝5.7Hz,2H),2.56(t,J＝5.7Hz,2H),2.48(t,J＝7.9Hz,2H),1.96–1.85(m,4H).13C NMR(100MHz,CDCl3,ppm)δ160.0,147.2,142.4,139.3,137.8,133.2,130.5,129.4,128.6,128.3,128.0,126.9,126.5,125.4,125.1,123.8,123.3,113.9,112.4,55.5,45.9,37.4,24.0,23.3,22.9,22.5.
实施例5产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.40(d,J＝9.4Hz,1H),8.33(d,J＝5.9Hz,2H),8.18(d,J＝9.4Hz,1H),7.63–7.53(m,2H),7.18(d,J＝8.6Hz,2H),6.79(d,J＝8.7Hz,2H),6.30(d,J＝6.1Hz,2H),4.99(s,2H),3.81(s,3H),3.25(t,J＝5.8Hz,2H),2.59(t,J＝5.9Hz,2H),1.99–1.94(m,4H).13C NMR(100MHz,CDCl3,ppm)δ159.7,149.7,147.5,147.1,142.4,139.2,132.1,129.9,129.4,127.9,127.5,125.8,125.4,123.7,123.2,120.2,113.5,113.2,55.4,46.8,23.9,23.2,22.6,22.4.
实施例6产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.38(d,J＝9.1Hz,1H),8.19(d,J＝7.8Hz,1H),7.61–7.52(m,2H),7.41(d,J＝8.6Hz,2H),7.04(d,J＝5.0Hz,1H),6.93(d,J＝8.6Hz,2H),6.73(t,J＝4.2Hz,1H),6.16(d,J＝2.6Hz,1H),5.13(s,2H),3.86(s,3H),3.23(t,J＝5.2Hz,2H),2.75(t,J＝5.2Hz,2H),1.97(p,J＝4.1Hz,4H).13C NMR(100MHz,CDCl3,ppm)δ159.8,147.3,142.6,141.0,139.4,132.6,130.1,129.4,128.2,127.5,126.4,125.6,125.1,124.3,124.0,123.8,123.3,113.7,113.4,55.4,43.6,24.0,23.3,22.8,22.5.
实施例7产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.42(d,J＝7.7Hz,1H),8.23(d,J＝9.2Hz,1H),7.58(p,J＝8.7,8.1Hz,2H),7.15–7.05(m,5H),6.89(d,J＝7.1Hz,2H),6.53(d,J＝8.6Hz,2H),3.72(s,3H),3.29(t,J＝6.2Hz,2H),2.57(t,J＝6.2Hz,2H),2.06–1.99(m,2H),1.94–1.86(m,2H).13C NMR(100MHz,CDCl3,ppm)δ158.8,147.4,142.9,139.7,137.9,131.7,130.1,129.5,128.1,128.0,127.9,126.9,125.6,125.1,123.7,123.3,112.8,112.7,55.2,24.0,23.9,23.3,22.5.
实施例8产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.41(d,J＝9.0Hz,1H),8.24(d,J＝7.7Hz,1H),7.57(p,J＝7.2Hz,2H),7.12(d,J＝8.6Hz,2H),6.60(dd,J＝13.3,8.6Hz,4H),6.33(d,J＝8.5Hz,2H),3.76(s,3H),3.65(s,2H),3.26(t,J＝6.2Hz,2H),2.55(t,J＝6.2Hz,2H),2.05–1.96(m,2H),1.91–1.86(m,2H).13C NMR(100MHz,CDCl3,ppm)δ158.9,147.5,145.5,142.5,140.2,131.6,130.4,129.3,128.9,128.6,128.2,127.6,125.5,125.0,123.7,123.3,114.1,112.8,112.2,55.4,24.1,23.8,23.4,22.6.
实施例9产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.35(d,J＝8.1Hz,1H),8.20(d,J＝7.8Hz,1H),7.58–7.51(m,4H),7.03(d,J＝8.5Hz,2H),3.88(s,3H),3.70(t,J＝8.2Hz,2H),3.21(t,J＝4.8Hz,2H),2.76(t,J＝5.0Hz,2H),1.99(q,J＝3.1Hz,4H),1.29–1.21(m,2H),1.19–1.11(m,2H),1.05–0.97(m,2H),0.85–0.77(m,5H).13C NMR(100MHz,CDCl3,ppm)δ159.7,147.2,142.2,138.9,133.2,130.1,129.3,127.4,127.1,125.2,125.0,123.8,123.2,113.6,112.2,55.4,44.5,31.2,31.1,26.1,24.0,23.3,22.9,22.6,22.4,13.9.
实施例10产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.35(d,J＝9.1Hz,1H),8.18(d,J＝9.3Hz,1H),7.57–7.50(m,4H),7.05(d,J＝8.5Hz,2H),4.15(t,J＝12.3Hz,1H),3.89(s,3H),3.24(t,J＝5.1Hz,2H),2.99(t,J＝5.0Hz,2H),1.96(p,J＝3.7Hz,4H),1.86–1.77(m,2H),1.67–1.63(m,4H),1.50(d,J＝13.1Hz,1H),1.08–0.96(m,1H),0.70(q,J＝13.0Hz,2H).13C NMR(100MHz,CDCl3,ppm)δ159.7,147.2,142.0,139.0,134.2,129.3,129.2,128.0,126.9,125.2,125.0,123.7,123.1,114.0,113.5,56.2,55.5,31.8,26.3,25.3,24.4,23.1.
实施例11产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.34(d,J＝9.4Hz,1H),8.12(d,J＝9.3Hz,1H),7.55–7.50(m,2H),7.38(d,J＝8.5Hz,2H),6.92(d,J＝8.5Hz,2H),3.83(t,J＝4.6Hz,5H),3.19(t,J＝5.7Hz,4H),2.78(t,J＝5.0Hz,2H),2.24(s,1H),1.94(p,J＝3.4Hz,4H).13C NMR(100MHz,CDCl3,ppm)δ159.8,146.8,142.1,140.5,132.6,130.2,129.0,128.1,127.1,125.6,125.2,123.7,123.2,113.6,112.3,62.0,55.3,46.1,24.0,23.3,23.2,22.5.
实施例12产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.35(d,J＝7.7Hz,1H),8.19(d,J＝8.2Hz,1H),7.58–7.50(m,4H),7.04(d,J＝8.5Hz,2H),3.89(s,3H),3.78(d,J＝7.8Hz,2H),3.19(t,J＝5.1Hz,2H),2.79(t,J＝4.9Hz,2H),2.05(s,6H),1.99–1.96(m,4H),1.73(t,J＝7.2Hz,2H),1.45–1.36(m,2H).13C NMR(100MHz,CDCl3,ppm)δ159.7,147.0,142.2,139.1,133.1,130.2,129.3,127.7,127.0,125.3,125.0,123.7,123.2,113.7,112.2,56.3,55.4,45.2,42.4,28.8,24.0,23.3,22.9,22.6.
实施例13产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.35(d,J＝7.7Hz,1H),8.19(d,J＝8.8Hz,1H),7.61–7.48(m,4H),7.03(d,J＝8.6Hz,2H),3.89(s,3H),3.82(t,J＝7.8Hz,2H),3.61(t,J＝4.6Hz,4H),3.19(t,J＝5.0Hz,2H),2.80(t,J＝4.4Hz,2H),2.19(t,J＝4.6Hz,4H),1.98(p,J＝2.8Hz,4H),1.82(t,J＝7.1Hz,2H),1.41(p,J＝7.3Hz,2H).13C NMR(100MHz,CDCl3,ppm)δ159.8,147.0,142.2,139.3,133.0,130.3,129.3,127.9,127.0,125.4,125.1,123.7,123.2,113.7,112.4,66.8,55.6,55.4,53.4,42.5,27.7,24.0,23.3,23.0,22.6.
实施例14产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.75(s,1H),8.30(d,J＝7.9Hz,1H),8.25(d,J＝8.1Hz,1H),7.86(d,J＝8.4Hz,2H),7.60–7.49(m,2H),7.02(d,J＝8.3Hz,2H),3.83(s,3H),3.17(t,J＝5.7Hz,2H),2.85(t,J＝5.7Hz,2H),1.99(p,J＝7.3,6.8Hz,4H).13C NMR(100MHz,CDCl3,ppm)δ160.4,145.5,142.8,137.5,130.6,129.7,129.1,127.2,126.4,125.6,125.1,123.8,123.4,114.5,113.0,55.4,23.7,23.6,23.4,22.5.
实施例15产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.45(d,J＝9.5Hz,1H),8.23(d,J＝8.1Hz,1H),7.86(d,J＝8.1Hz,1H),7.78(d,J＝8.4Hz,1H),7.68(s,1H),7.63–7.57(m,2H),7.55–7.48(m,2H),7.48–7.40(m,2H),7.11(t,J＝7.3Hz,1H),7.02(t,J＝7.5Hz,2H),6.21(d,J＝7.6Hz,2H),4.94(s,2H),3.30(t,J＝6.0Hz,2H),2.66(t,J＝6.0Hz,2H),2.03–1.94(m,4H).13C NMR(100MHz,CDCl3,ppm)δ147.5,142.3,139.9,138.0,137.3,133.0,132.8,129.5,128.3,128.3,128.2,127.8,127.6,127.5,126.9,126.6,126.2,126.1,125.6,125.3,124.9,123.9,123.3,112.8,47.8,24.1,23.3,22.7,22.5.
实施例16产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.41(d,J＝9.3Hz,1H),8.21(d,J＝8.9Hz,1H),7.63–7.55(m,2H),7.38(d,J＝4.6Hz,1H),7.19–7.10(m,3H),6.94(d,J＝4.6Hz,2H),6.49(d,J＝4.0Hz,2H),5.12(s,2H),3.26(t,J＝5.9Hz,2H),2.65(t,J＝5.8Hz,2H),2.02–1.90(m,4H).13C NMR(100MHz,CDCl3,ppm)δ142.2,140.5,140.2,138.3,129.5,128.4,128.1,128.0,126.9,126.7,126.5,125.7,125.6,125.0,124.0,123.3,112.9,47.6,24.0,23.3,22.8,22.4.
实施例17产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ9.23(s,1H),8.45(d,J＝9.5Hz,1H),8.20(d,J＝9.5Hz,1H),7.58(d,J＝9.5Hz,2H),7.31(d,J＝7.9Hz,1H),7.22(d,J＝8.1Hz,1H),7.11(t,J＝7.5Hz,1H),7.07–6.96(m,4H),6.73(s,1H),6.31(d,J＝7.1Hz,2H),4.96(s,2H),3.29(t,J＝6.0Hz,2H),2.63(t,J＝5.9Hz,2H),2.02–1.94(m,4H).13C NMR(100MHz,CDCl3,ppm)δ150.8,142.4,142.2,139.9,138.7,135.4,128.9,128.3,128.2,127.6,126.7,125.5,125.1,124.8,124.3,123.9,123.4,122.0,120.1,119.4,114.4,112.7,111.5,47.3,24.1,23.4,22.7,22.5.
实施例18产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.32(d,J＝8.0Hz,1H),8.07(d,J＝8.0Hz,1H),7.53–7.45(,2H),7.28–7.20(m,3H),6.88–6.78(m,2H),5.56(s,2H),3.21(t,J＝4.9Hz,2H),3.13(t,J＝11.3Hz,1H),2.71(t,J＝5.1Hz,2H),1.97(q,J＝3.0Hz,4H),1.89(t,J＝12.0Hz,2H),1.79–1.65(m,5H),1.37–1.26(m,1H),1.14(q,J＝12.7Hz,2H).13C NMR(100MHz,CDCl3,ppm)δ153.1,142.7,138.6,138.2,129.1,128.9,127.3,127.2,125.0,124.5,123.5,123.1,112.4,48.6,42.1,32.5,26.7,26.0,24.2,23.4,22.7,22.6.
实施例19产物的核磁数据如下：
1H NMR(400MHz,CDCl3,ppm)δ8.88(s,1H),8.31(d,J＝9.1Hz,1H),8.16(d,J＝8.7Hz,1H),7.61–7.51(m,2H),7.27–7.21(m,3H),6.96(d,J＝7.0Hz,2H),5.38(s,2H),3.16(t,J＝5.1Hz,2H),2.67(t,J＝5.1Hz,2H),1.94(p,J＝3.6Hz,4H).13C NMR(100MHz,CDCl3,ppm)δ142.9,138.4,137.1,135.6,129.4,129.1,128.9,127.6,126.0,126.0,125.4,125.3,124.2,123.5,112.2,46.6,23.7,23.2,22.4.
以上述依据本发明的理想实施例为启示，通过上述的说明内容，相关工作人员完全可以在不偏离本项发明技术思想的范围内，进行多样的变更以及修改。本项发明的技术性范围并不局限于说明书上的内容，必须要根据权利要求范围来确定其技术性范围。
Claims (3)
1.一种合成吡咯并喹啉及其衍生物的方法，其特征在于，将3-环己酮基吲哚类化合物、胺类化合物和醛类化合物三组分在催化剂、碱、有机溶剂的反应条件下经加热搅拌得到；
所述3-环己酮基吲哚类化合物选自以下中的一种：
所述胺类化合物选自以下中的一种：
所述醛类化合物选自以下中的一种：
所述催化剂为：NH4I、单质碘、KI、NIS、IBr、I2O5、NaIO4中的一种；
所述碱为：NaHCO3、Na2CO3、Li2CO3、KHCO3、K2HPO4、醋酸钠、吡啶、吗啉、三乙胺中的一种；
所述吡咯并喹啉及其衍生物的结构式为以下中的一种：
2.根据权利要求1所述的方法，其特征在于，所述有机溶剂选自氯苯、甲苯、三氟甲苯、对二甲苯、1，4-二氧六环、乙腈、环己烷、吡啶、乙基苯、苯甲醚中的一种，所述溶剂的用量为：0-1.0mL。
3.根据权利要求1或2所述的方法，其特征在于，所述3-环己酮基吲哚类化合物、胺类化合物、醛类化合物、催化剂、碱的摩尔比为1.0∶1.0-2.0∶1.0-2.0∶0.05-0.5∶0-4.0；反应温度为130℃-160℃；反应容器的气氛为：空气或氧气氛围；反应时长为2h-16h。
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