CN110041367A - 光催化合成膦酰化二氢异喹啉酮类化合物 - Google Patents
光催化合成膦酰化二氢异喹啉酮类化合物 Download PDFInfo
- Publication number
- CN110041367A CN110041367A CN201910451671.2A CN201910451671A CN110041367A CN 110041367 A CN110041367 A CN 110041367A CN 201910451671 A CN201910451671 A CN 201910451671A CN 110041367 A CN110041367 A CN 110041367A
- Authority
- CN
- China
- Prior art keywords
- dihydro
- phosphonylation
- ketone compounds
- isoquinoline ketone
- methyl
- 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.)
- Pending
Links
- -1 dihydro-isoquinoline ketone compounds Chemical class 0.000 title claims abstract description 37
- 238000005954 phosphonylation reaction Methods 0.000 title claims abstract description 29
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 230000001699 photocatalysis Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229930015698 phenylpropene Natural products 0.000 claims abstract description 13
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- 238000005286 illumination Methods 0.000 claims abstract description 4
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 6
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- GYYTYUGGVBYJHE-UHFFFAOYSA-L disodium;2-(4,5-dibromo-2,7-dinitro-3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C([N+]([O-])=O)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C([N+]([O-])=O)C=C21 GYYTYUGGVBYJHE-UHFFFAOYSA-L 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000000975 dye Substances 0.000 abstract description 2
- 238000004440 column chromatography Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 78
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 28
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000004679 31P NMR spectroscopy Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 8
- 238000010998 test method Methods 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- XCQQWDCKLLORFE-UHFFFAOYSA-N [O].C1(=CC=CC=C1)PC1=CC=CC=C1 Chemical compound [O].C1(=CC=CC=C1)PC1=CC=CC=C1 XCQQWDCKLLORFE-UHFFFAOYSA-N 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000010523 cascade reaction Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- YWPMKTWUFVOFPL-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one Chemical class C1=CC=C2C(=O)NCCC2=C1 YWPMKTWUFVOFPL-UHFFFAOYSA-N 0.000 description 1
- KJDLQEJTNPEOLU-UHFFFAOYSA-N C1=CC=C2C(P(=O)=O)=CNC2=C1 Chemical class C1=CC=C2C(P(=O)=O)=CNC2=C1 KJDLQEJTNPEOLU-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- ZHIPXAFNKGZMSC-UHFFFAOYSA-N bis(4-methylphenyl)-oxophosphanium Chemical group C1=CC(C)=CC=C1[P+](=O)C1=CC=C(C)C=C1 ZHIPXAFNKGZMSC-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000006872 improvement Effects 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
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- LQFLWKPCQITJIH-UHFFFAOYSA-N n-allyl-aniline Chemical compound C=CCNC1=CC=CC=C1 LQFLWKPCQITJIH-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/62—Isoquinoline or hydrogenated isoquinoline ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种膦酰化二氢异喹啉酮类化合物及其制备方法,以有机染料为光敏剂,添加当量碱,加入当量氧化剂,将N‑烯丙基苯甲酰胺、氧化膦为反应物,二甲基亚砜为溶剂,温度控制在25‑45℃,在可见光照射下反应12‑24 h后,经过柱层析分离到产物膦酰化二氢异喹啉酮类化合物。
Description
技术领域
本发明涉及化学合成领域,具体涉及一种膦酰化二氢异喹啉酮类化合物的制备方法。
背景技术
二氢异喹啉酮骨架是多种天然产物,药物和生物活性分子的核心,其优异的药理活性引起了广泛的关注,在抗恶心、抗肿瘤和抗癌等药物中具有非常有前景的应用。有机膦化合物在生物化学、药物化学和材料化学中发挥着重要作用。目前,药物研究和材料开发的主要目标之一是将膦取代基引入生物活性分子中,以改变药物性质、生物反应和材料。因此我们希望得到膦取代的二氢异喹啉酮类化合物。传统的二氢异喹啉酮类化合物的合成方法主要依赖于邻苯二甲酸酐与亚胺的缩合或苯甲酰胺与烯烃的氧化环化反应(如:Org.Lett. 2008, 10, 4759;Org. Lett. 2014, 16, 4684)。然而,这类传统方法都存在着反应条件苛刻的问题。串联反应是以一锅法快速构建多个化学键的有力策略。在串联反应中可避免中间体的分离、保护/脱保护等步骤。近来,银催化的N-烯丙基苯胺的膦酰化串联环化反应可用于合成3-膦酰吲哚啉(J. Org. Chem. 2018, 83, 4681)。此前,我们在银催化下以N-甲基-N-(2-甲基烯丙基)苯甲酰胺和氧化膦为原料,实现了膦酰化二氢异喹啉酮类化合物的合成(发明专利CN2019104366999)。但是前述体系需要使用过量的银盐作为促进剂,成本较高。因此,针对该反应开发无过渡金属参与的新型合成路线具有重要应用价值。本发明采用可见光催化的方法,有机染料为催化剂,实现了温和条件下膦酰化二氢异喹诺酮类化合物的合成。本发明中所公布的无过渡金属光催化体系没有相关文献及专利报道。
发明内容
本发明提出了一种膦酰化二氢异喹啉酮类化合物的制备方法,提供一种温和、廉价、无过度金属的可见光催化方法合成膦酰化二氢异喹啉酮。该合成方法反应条件温和,在可见光照条件下,使用了无金属光敏剂,具有步骤经济性,原料、催化剂价廉易得的优点,是一种环境友好的绿色合成方法。
实现本发明的技术方案是:一种膦酰化二氢异喹啉酮类化合物,结构式如下:
其中,R1为氢、甲基、甲氧基、氯、溴、碘;R2为甲基、乙基、异丙基;R3为苯基、对甲基苯基、对氯苯基。
所述的膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:将N-烯丙基苯甲酰胺、氧化膦和溶剂加入反应管中,随后向其中加入碱、光敏剂和氧化剂,在可见光照射下于氮气氛围中、搅拌条件下反应,得到膦酰化二氢异喹啉酮类化合物。
所述N-烯丙基苯甲酰胺的结构式如下:
其中R1为氢、甲基、甲氧基、氯、溴、碘;R2为甲基、乙基、异丙基。
所述氧化膦的结构式如下:
其中R3为苯基、对甲基苯基、对氯苯基。
所述溶剂为乙腈、N,N-二甲基甲酰胺或二甲基亚砜中的任意一种;碱为三乙烯二胺、三乙胺和碳酸氢钠中的任意一种;光敏剂为曙红Y和曙红B钠盐中的任意一种;氧化剂为叔丁基过氧化氢和过氧化二苯甲酰的任意一种。
所述N-烯丙基苯甲酰胺、氧化膦、碱、光敏剂和氧化剂的摩尔比为1:(2-3):2:0.05:2。
所述的反应温度为25-45 ℃,反应时间为12-24 h。
本发明所述制备方法的反应通式如下:
本发明的有益效果是:本发明提供了一种膦酰化二氢异喹啉酮类化合物的制备方法,所述方法不需要添加金属催化剂,在可见光照射下使用廉价易得的光敏剂作催化剂来高效合成膦酰化二氢异喹啉酮类化合物。该方法所涉及的操作简便安全、具有反应条件温和、无过度金属、经济性好、环境友好的优点。
具体实施方式
下面将结合本发明实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂曙红Y (5 mol%),碳酸氢钠 (2 equiv),溶剂二甲基亚砜3 mL,N-甲基-N-(2-甲基烯丙基)苯甲酰胺0.5 mmol,二苯基膦氧1.0 mmol,叔丁基过氧化氢1.0 mmol,在氮气氛围中搅拌控制反应温度为35 ℃,于白光照射下反应24小时后,硅胶柱层析分离得到最终产物,以N-甲基-N-(2-甲基烯丙基)苯甲酰胺摩尔量为100 %计,终产物的产率为78%。
具体结果如下:
1H NMR (400 MHz, CDCl3): δ 8.02 (dd, J = 7.7, 1.1 Hz, 1H), 7.69 - 7.62(m, 4H), 7.48 - 7.38 (m, 6H), 7.36 - 7.30 (m, 1H), 7.29 - 7.21 (m, 2H), 3.81(d, J = 12.7 Hz, 1H), 3.50 (d, J = 12.7 Hz, 1H), 3.00 (s, 3H), 2.75 - 2.64(m, 1H), 2.59 - 2.50 (m, 1H), 1.58 (s, 3H); 13C NMR (101 MHz, CDCl3): δ 164.6,145.3 (d, J = 10.7 Hz), 134.8 (d, J = 98.9 Hz), 133.4 (d, J = 98.4 Hz),132.1, 131.7 (d, J = 2.8 Hz), 131.4 (d, J = 2.8 Hz), 130.5 (d, J = 9.0 Hz),130.2 (d, J = 9.3 Hz), 128.8, 128.7 (d, J = 7.6 Hz), 128.6 (d, J = 6.6 Hz),127.8, 127.3, 123.8, 58.1 (d, J = 4.9 Hz), 37.9 (d, J = 67.7 Hz), 37.4 (d, J= 3.6 Hz), 34.8, 23.1 (d, J = 1.4 Hz); 31P NMR (162 MHz, CDCl3): δ 27.38; HRMSCalcd for C24H24NO2P [M + H]+: 390.1617, found: 390.1606。
实施例2
膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂曙红B钠盐 (5 mol%),三乙烯二胺 (2 equiv),溶剂乙腈3 mL,N,4-二甲基-N-(2-甲基烯丙基)苯甲酰胺0.5 mmol,二苯基膦氧1.0 mmol,叔丁基过氧化氢1.0 mmol,在氮气氛围中搅拌控制反应温度为25 ℃,于白光照射下反应12小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 7.9 Hz, 1H), 7.71 - 7.58 (m, 3H),7.52 - 7.32 (m, 6H), 7.05 (d, J = 1.6 Hz, 1H), 6.99 (dd, J = 7.6, 1.6 Hz,1H), 3.69 (d, J = 12.7 Hz, 1H), 3.48 (dd, J = 12.7, 1.5 Hz, 1H), 3.00 (s,3H), 2.78 - 2.49 (m, 2H), 2.26 (s, 3H), 1.60 (s, 3H); 13C NMR (101 MHz, CDCl3)δ 164.8, 144.9 (d, J = 9.6 Hz), 142.50, 134.9 (d, J = 98.5 Hz), 133.3 (d, J =98.1 Hz), 131.6 (d, J = 2.7 Hz), 131.3 (d, J = 2.8 Hz), 130.3 (d, J = 9.0Hz), 130.1 (d, J = 9.2 Hz), 128.8 (d, J = 11.1 Hz), 128.7, 128.5 (d, J = 11.6Hz), 128.1, 125.2, 124.7, 58.7 (d, J = 6.1 Hz), 37.9 (d, J = 68.0 Hz), 37.4(d, J = 3.6 Hz), 34.8, 23.1 (d, J = 1.8 Hz), 21.7; 31P NMR (162 MHz, CDCl3): δ27.38; HRMS Calcd for C25H26NO2P [M + H]+:404.1774, found: 404.1762。
实施例3
膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂曙红Y (5 mol%),三乙烯二胺 (2 equiv),溶剂N,N-二甲基甲酰胺3 mL,4-甲氧基-N-甲基-N-(2-甲基烯丙基)苯甲酰胺0.5 mmol,二苯基膦氧1.5mmol,叔丁基过氧化氢1.0 mmol,在氮气氛围中搅拌控制反应温度为35 ℃,于白光照射下反应18小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (400 MHz, CDCl3) δ 7.95 (d, J = 8.6 Hz, 1H), 7.68 - 7.60 (m, 4H),7.48 - 7.34 (m, 6H), 6.76 (d, J = 2.5 Hz, 1H), 6.68 (dd, J = 8.6, 2.5 Hz,1H), 3.77 (s, 3H), 3.67 (d, J = 12.6 Hz, 1H), 3.48 (d, J = 12.5 Hz, 1H), 2.99(s, 3H), 2.67 - 2.55 (m, 2H), 1.59 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 164.6,162.4, 147.0 (d, J = 9.7 Hz), 134.9 (d, J = 98.7 Hz), 133.2 (d, J = 98.1 Hz),131.6 (d, J = 2.7 Hz), 131.3 (d, J = 2.7 Hz), 130.8, 130.3 (d, J = 9.0 Hz),130.1 (d, J = 9.1 Hz), 128.7 (d, J = 11.6 Hz), 128.5 (d, J = 11.7 Hz), 120.7,112.1, 109.9, 58.7 (d, J = 6.1 Hz), 55.3, 37.8 (d, J = 68.3 Hz), 37.5 (d, J =3.6 Hz), 34.7, 23.1 (d, J = 1.8 Hz); 31P NMR (162 MHz, CDCl3): δ 27.46; HRMSCalcd for C25H26NO3P [M + H]+:420.1723, found: 420.1716。
实施例4
膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂曙红Y (5 mol%),三乙胺 (2 equiv),溶剂N,N-二甲基甲酰胺3 mL,4-氯-N-甲基-N-(2-甲基烯丙基)苯甲酰胺0.5 mmol,二苯基膦氧1.0 mmol,过氧化二苯甲酰(2 equiv),在氮气氛围中搅拌控制反应温度为35 ℃,于白光照射下反应24小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (400 MHz, CDCl3): δ 7.91 (d, J = 8.4 Hz, 1H), 7.72 - 7.59 (m, 4H),7.52 - 7.37 (m, 6H), 7.24, (d, J = 1.3 Hz, 1H), 7.16 (dd, J = 8.3, 1.3 Hz,1H), 3.77 (d, J = 12.8 Hz, 1H), 3.51 (d, J = 12.8 Hz, 1H), 3.03 (s, 3H), 2.71- 2.50 (m, 2H), 1.58 (s, 3H); 13C NMR (101 MHz, CDCl3): δ 163.8, 146.6 (d, J =9.9 Hz), 138.3, 134.7 (d, J = 98.8 Hz), 132.9 (d, J = 98.6 Hz), 131.8 (d, J =2.7 Hz), 131.6 (d, J = 2.6 Hz), 130.5, 130.4 (d, J = 9.8 Hz), 130.1 (d, J =9.2 Hz), 128.8 (d, J = 11.6 Hz), 128.6 (d, J = 11.7 Hz), 127.7, 126.4, 124.6,58.4 (d, J = 5.7 Hz), 37.7 (d, J = 68.0 Hz), 37.5 (d, J = 3.3 Hz), 34.9, 23.1(d, J = 1.5 Hz); 31P NMR (162 MHz, CDCl3): δ 27.17; HRMS Calcd for C24H24NO2P [M+ H]+: 424.1228, found: 424.1221。
实施例5
膦酰化二氢异喹啉酮类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂曙红Y (5 mol%),碳酸氢钠 (2 equiv),溶剂乙腈3 mL,4-溴-N-甲基-N-(2-甲基烯丙基)苯甲酰胺0.5 mmol,二苯基膦氧1.0 mmol,叔丁基过氧化氢1.0 mmol,在氮气氛围中搅拌控制反应温度为45 ℃,于白光照射下反应20小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (400 MHz, CDCl3): δ 7.83 (d, J = 8.3 Hz, 1H), 7.68 - 7.63 (m, 4H),7.48 - 7.39 (m, 7H), 7.34 - 7.30 (dd, J = 8.3, 1.9 Hz, 1H), 3.77 (d, J = 12.8Hz, 1H), 3.50 (d, J = 12.8 Hz, 1H), 3.03 (s, 3H), 2.68 - 2.52 (m, 2H), 1.58(s, 3H); 13C NMR (101 MHz, CDCl3): δ 163.8, 146.7 (d, J = 9.8 Hz), 134.7 (d, J = 99.7 Hz), 132.9 (d, J = 98.5 Hz), 131.8 (d, J = 2.7 Hz), 131.6 (d, J = 2.8Hz), 130.6 (d, J = 19.5 Hz), 130.4, 130.1 (d, J = 9.2 Hz), 128.8 (d, J = 11.7Hz), 128.6 (d, J = 11.7 Hz), 127.5, 127.0, 126.8, 58.4 (d, J = 5.8 Hz), 37.7(d, J = 68.0 Hz), 37.5 (d, J = 3.6 Hz), 34.9, 23.0 (d, J = 1.5 Hz); 31P NMR(162 MHz, CDCl3): δ 27.11; HRMS Calcd for C24H23BrNO2P [M + H]+: 468.0723,found: 468.0721。
实施例6
N-烯丙基苯甲酰胺为4-碘-N-甲基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3): δ 7.68 - 7.60 (m, 6H) 7.55 (dd, J = 8.2, 1.5 Hz,1H), 7.50 - 7.40 (m, 6H), 3.74 (d, J = 12.8 Hz, 1H), 3.50 (d, J = 12.9 Hz,1H), 3.02 (s, 3H), 2.65 - 2.53 (m, 2H), 1.57 (s, 3H); 13C NMR (101 MHz,CDCl3): δ 164.0, 146.5 (d, J = 9.6 Hz), 136.8, 134.7 (d, J = 99.5 Hz), 133.5,132.8 (d, J = 98.4 Hz), 131.8 (d, J = 2.6 Hz), 131.6 (d, J = 2.8 Hz), 130.5(d, J = 9.3 Hz), 130.2, 130.1 (d, J = 9.1 Hz), 128.8 (d, J = 11.8 Hz), 128.7(d, J = 11.9 Hz), 127.4, 99.9, 58.4 (d, J = 5.9 Hz), 37.7 (d, J = 66.8 Hz),37.4 (d, J = 2.6 Hz), 35.0, 23.0 (d, J = 1.5 Hz); 31P NMR (162 MHz, CDCl3): δ27.17; HRMS Calcd for C24H23INO2P [M + H]+: 516.0584, found: 516.0590。
实施例7
N-烯丙基苯甲酰胺为N,2-二甲基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3): δ 7.70 - 7.61 (m, 4H), 7.49 - 7.35 (m, 6H), 7.19- 7.10 (m, 2H), 7.00 (d, J = 7.1 Hz, 1H), 3.75 (d, J = 12.8 Hz, 1H), 3.47 (d,J = 12.8 Hz, 1H), 3.08 (s, 3H), 2.69 - 2.59 (m, 4H), 2.58 - 2.50 (m, 1H),1.53 (s, 3H); 13C NMR (101 MHz, CDCl3): δ 165.1, 146.3 (d, J = 10.0 Hz),141.0, 135.1 (d, J = 98.9 Hz), 133.2 (d, J = 98.2 Hz), 131.6 (d, J = 2.5 Hz),131.1, 131.0, 130.6 (d, J = 9.0 Hz), 130.1 (d, J = 9.4 Hz), 128.7 (d, J =11.7 Hz), 128.4 (d, J = 11.7 Hz), 126.5, 121.9, 57.9 (d, J = 5.1 Hz), 38.0(d, J = 3.6 Hz), 37.2 (d, J = 68.1 Hz), 35.0, 23.4 (d, J = 1.5 Hz), 22.7; 31PNMR (162 MHz, CDCl3): δ 27.57; HRMS Calcd for C25H26NO2P [M + H]+: 404.1774,found: 404.1768。
实施例8
N-烯丙基苯甲酰胺为3-氯-N-甲基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3) δ 7.91 (d, J = 2.2 Hz, 1H), 7.66 - 7.55 (m, 4H),7.50 - 7.35 (m, 6H), 7.24 - 7.17 (m, 2H), 3.68 (d, J = 12.8 Hz, 1H), 3.51 (d,J = 12.8 Hz, 1H), 3.04 (s, 3H), 2.63 - 2.54 (m, 2H), 1.62 (s, 3H); 13C NMR(101 MHz, CDCl3) δ 163.3, 142.9 (d, J = 8.9 Hz), 134.7 (d, J = 99.2 Hz),133.6, 132.7 (d, J = 98.3 Hz), 131.8, 131.7 (d, J = 2.9 Hz), 131.3 (d, J =2.8 Hz), 130.5 (d, J = 9.0 Hz), 130.1 (d, J = 9.2 Hz), 129.5, 128.8 (d, J =11.5 Hz), 128.6 (d, J = 11.7 Hz), 128.4, 126.1, 58.8 (d, J = 6.7 Hz), 38.0(d, J = 68.4 Hz), 37.2 (d, J = 3.6 Hz), 35.1, 23.2 (d, J = 1.2 Hz); 31P NMR(162 MHz, CDCl3): δ 27.57; HRMS Calcd for C24H23ClNO2P [M + H]+:424.1228,found: 424.1223。
实施例9
N-烯丙基苯甲酰胺为3-溴-N-甲基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3) δ 8.05 (d, J = 2.2 Hz, 1H), 7.66 - 7.61 (m, 2H),7.59 - 7.54 (m, 2H), 7.47 - 7.32 (m, 7H), 7.16 (d, J = 8.3 Hz, 1H), 3.66 (d,J = 12.8 Hz, 1H), 3.50 (dd, J = 12.8, 2.0 Hz, 1H), 3.04 (s, 3H), 2.66 – 2.58(m, 2H), 1.62 (s, 3H); 13C NMR (101 MHz, CDCl3) δ 163.2, 143.3 (d, J = 8.9Hz), 134.68 (d, J = 99.5 Hz), 134.71, 132.6 (d, J = 98.4 Hz), 131.7 (d, J =2.9 Hz), 131.3, 130.5 (d, J = 9.1 Hz), 130.1 (d, J = 9.3 Hz), 129.7, 128.8(d, J = 11.7 Hz), 128.6 (d, J = 11.7 Hz), 126.4, 121.6, 58.8 (d, J = 6.7 Hz),37.9 (d, J = 68.3 Hz), 37.2 (d, J = 3.6 Hz), 35.1, 23.1 (d, J = 1.4 Hz); 31PNMR (162 MHz, CDCl3): δ 27.57; HRMS Calcd for C24H23BrNO2P [M + H]+:468.0723,found: 468.0721。
实施例10
N-烯丙基苯甲酰胺为N-乙基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3): δ 8.02 (d, J = 7.6 Hz, 1H), 7.73 - 7.58 (m, 4H),7.49 - 7.36 (m, 6H), 7.31 (t, J = 7.2 Hz, 1H), 7.26 - 7.20 (m, 2H), 3.88 (d,J = 12.7 Hz, 1H), 3.83 - 3.70 (m, 1H), 3.51 (d, J = 12.6 Hz, 1H), 3.45 – 3.30(m, 1H), 2.76 - 2.64 (m, 1H), 2.61 - 2.48 (m, 1H),1.55 (s, 3H), 1.21 (t, J =7.2 Hz, 3H); 13C NMR (101 MHz, CDCl3): δ 163.8, 145.2 (d, J = 10.4 Hz), 135.1(d, J = 99.1 Hz), 133.4 (d, J = 98.1 Hz), 132.0, 131.6 (d, J = 2.6 Hz), 131.4(d, J = 2.8 Hz), 130.5 (d, J = 9.0 Hz), 130.0 (d, J = 9.4 Hz), 128.8, 128.7,128.6, 128.2, 127.3, 123.8, 56.0 (d, J = 4.8 Hz), 42.1, 37.36 (d, J = 3.6Hz), 37.41 (d, J = 68.2 Hz), 23.1 (d, J = 2.2 Hz) 12.6; 31P NMR (162 MHz,CDCl3): δ 27.39; HRMS Calcd for C25H26NO2P [M + H]+: 404.1774, found: 404.1762。
实施例11
N-烯丙基苯甲酰胺N-异丙基-N-(2-甲基烯丙基)苯甲酰胺,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3) δ 8.00 (dd, J = 7.7, 1.3 Hz, 1H), 7.66 -7.59 (m,4H), 7.45 - 7.36 (m, 6H), 7.27 - 7.23 (m, 2H), 7.32 - 7.17 (m, 1H), 5.15 -5.04(m, 1H), 3.79 (d, J = 12.8 Hz, 1H), 3.30 (dd, J = 12.7, 1H), 2.68 - 2.56(m, 2H), 1.58 (s, 3H), 1.27 (d, J = 6.8 Hz, 3H), 1.19 (d, J = 6.8 Hz, 3H); 13CNMR (101 MHz, CDCl3) δ 163.5, 144.3 (d, J = 9.2 Hz), 135.4 (d, J = 99.0 Hz),133.3 (d, J = 97.8 Hz), 131.9, 131.5 (d, J = 2.8 Hz), 131.3 (d, J = 2.8 Hz),130.5 (d, J = 9.1 Hz), 129.9 (d, J = 9.1 Hz), 128.8, 128.7 (d, J = 11.5 Hz),128.6 (d, J = 11.7 Hz), 128.5, 127.3, 124.0, 50.4 (d, J = 5.8 Hz), 43.9, 37.0(d, J = 3.5 Hz), 36.7 (d, J = 69.2 Hz), 23.4 (d, J = 2.6 Hz), 20.0, 19.3; 31PNMR (162 MHz, CDCl3): δ 27.11; HRMS Calcd for C25H26NO2P [M + H]+: 418.1930,found: 418.1921。
实施例12
氧化膦为二对甲苯基氧化膦,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3): δ 8.03 (dd, J = 7.9 Hz, 1.3 Hz, 1H), 7.57 - 7.50(m, 4H), 7.37 - 7.31 (m, 1H), 7.27 - 7.24 (m, 2H),7.23 -7.19 (m, 4H), 3.85(d, J = 12.7 Hz, 1H), 3.48 (d, J = 12.7 Hz, 1H), 3.00 (s, 3H), 2.73 - 2.63(m, 1H),2.51 -2.42 (m, 1H),2.36 (s, 3H),2.35 (s, 3H), 1.56 (s, 3H); 13C NMR(101 MHz, CDCl3): δ 164.6, 145.8 (d, J = 11.0 Hz), 142.1 (d, J = 2.7 Hz),141.8 (d, J = 2.8 Hz), 132.1, 131.7 (d, J = 101.5 Hz), 130.5 (d, J = 9.5 Hz),130.4 (d, J = 100.7 Hz), 130.2 (d, J = 9.6 Hz), 129.5 (d, J = 12.5 Hz), 129.3(d, J = 12.6 Hz), 128.6, 127.8, 127.2, 123.7, 57.9 (d, J = 4.4 Hz), 38.1 (d,J = 67.5 Hz), 37.4 (d, J = 3.6 Hz), 34.8, 23.1 (d, J = 1.5 Hz), 21.5; 31P NMR(162 MHz, CDCl3): δ 27.76; HRMS Calcd for C26H28NO2P [M + H]+: 418.1930, found:418.1923。
实施例13
氧化膦为二对氯苯基氧化膦,其他试验方法和条件同实施例1,具体结果如下:
1H NMR (400 MHz, CDCl3): δ 8.00 - 7.98 (m, 1H), 7.55 - 7.47 (m, 4H), 7.40- 7.32 (m, 4H), 7.29 - 7.20 (m, 3H), 3.80 - 3.70 (m, 2H), 3.56 - 3.40 (m,2H), 2.59 (d, J = 10.5 Hz, 2H), 1.60 (s, 3H), 1.22 (t, J = 7.2 Hz, 3H); 13CNMR (101 MHz, CDCl3): δ 163.8, 144.1 (d, J = 9.1 Hz), 138.5 (d, J = 3.4 Hz),138.2 (d, J = 3.5 Hz), 133.2 (d, J = 100.9 Hz), 132.0, 131.8 (d, J = 9.8 Hz),131.3 (d, J = 10.1 Hz), 131.1 (d, J = 99.7 Hz), 129.2 (d, J = 12.3 Hz), 129.0(d, J = 12.2 Hz), 128.7, 128.2, 127.5, 124.2, 56.7 (d, J = 6.7 Hz), 42.1,37.4 (d, J = 69.9 Hz), 37.3 (d, J = 3.6 Hz), 23.1 (d, J = 1.8 Hz) 12.6; 31PNMR (162 MHz, CDCl3): δ 26.66; HRMS Calcd for C25H24Cl2NO2P [M + H]+: 471.0922,found: 471.0920。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (8)
1.一种膦酰化二氢异喹啉酮类化合物,其特征在于结构式如下:
其中,R1为氢、甲基、甲氧基、氯、溴、碘;R2为甲基、乙基、异丙基;R3为苯基、对甲基苯基、对氯苯基。
2.膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于步骤如下:将N-烯丙基苯甲酰胺、氧化膦和溶剂加入反应管中,随后加入碱、光敏剂和氧化剂,在可见光照射下于氮气氛围中、搅拌条件下反应,得到膦酰化二氢异喹啉酮类化合物。
3.根据权利要求2所述的膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于所述N-烯丙基苯甲酰胺的结构式如下:
其中R1为氢、甲基、甲氧基、氯、溴、碘;R2为甲基、乙基、异丙基。
4.根据权利要求2所述的膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于所述氧化膦的结构式如下:
其中R3为苯基、对甲基苯基、对氯苯基。
5.根据权利要求2所述的膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于:所述溶剂为乙腈、N,N-二甲基甲酰胺或二甲基亚砜中的任意一种;碱为三乙烯二胺、三乙胺和碳酸氢钠中的任意一种;光敏剂为曙红Y和曙红B钠盐中的任意一种;氧化剂为叔丁基过氧化氢和过氧化二苯甲酰的任意一种。
6.根据权利要求2所述N-烯丙基苯甲酰胺、氧化膦、碱、光敏剂和氧化剂的摩尔比为1:(2-3):2:0.05:2。
7.根据权利要求2所述的膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于:所述的反应温度为25-45 ℃,反应时间为12-24 h。
8.根据权利要求2-7任一项所述的膦酰化二氢异喹啉酮类化合物的制备方法,其特征在于所述膦酰化二氢异喹啉酮类化合物的结构式如下:
其中,R1为氢、甲基、甲氧基、氯、溴、碘;R2为甲基、乙基、异丙基;R3为苯基、对甲基苯基、对氯苯基。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910451671.2A CN110041367A (zh) | 2019-05-28 | 2019-05-28 | 光催化合成膦酰化二氢异喹啉酮类化合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910451671.2A CN110041367A (zh) | 2019-05-28 | 2019-05-28 | 光催化合成膦酰化二氢异喹啉酮类化合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN110041367A true CN110041367A (zh) | 2019-07-23 |
Family
ID=67283843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201910451671.2A Pending CN110041367A (zh) | 2019-05-28 | 2019-05-28 | 光催化合成膦酰化二氢异喹啉酮类化合物 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN110041367A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110845411A (zh) * | 2019-11-07 | 2020-02-28 | 江苏理工学院 | 一种多氯甲基取代二氢异喹啉酮化合物的合成方法 |
CN114644655A (zh) * | 2022-04-19 | 2022-06-21 | 湖南农业大学 | 一种光催化磷酰化喹唑啉酮类化合物的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109734662A (zh) * | 2019-02-28 | 2019-05-10 | 郑州大学 | 一种三氟甲基取代二氢异喹啉酮衍生物及其制备方法 |
CN110003274A (zh) * | 2019-05-23 | 2019-07-12 | 郑州大学 | 膦酰化二氢异喹啉酮类化合物及其制备方法 |
-
2019
- 2019-05-28 CN CN201910451671.2A patent/CN110041367A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109734662A (zh) * | 2019-02-28 | 2019-05-10 | 郑州大学 | 一种三氟甲基取代二氢异喹啉酮衍生物及其制备方法 |
CN110003274A (zh) * | 2019-05-23 | 2019-07-12 | 郑州大学 | 膦酰化二氢异喹啉酮类化合物及其制备方法 |
Non-Patent Citations (2)
Title |
---|
JING ZHENG ET AL.: "Silver(I)-Mediated Phosphorylation/Cyclization Cascade of N-Cyanamide Alkenes for Divergent Access to Quinazolinones and Dihydroisoquinolinones", 《ORGANIC LETTERS》 * |
WANGQING KONG ET AL.: "Arylphosphonylation and Arylazidation of Activated Alkenes", 《ANGEWANDTE CHEMIE, INTERNATIONAL EDITION》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110845411A (zh) * | 2019-11-07 | 2020-02-28 | 江苏理工学院 | 一种多氯甲基取代二氢异喹啉酮化合物的合成方法 |
CN110845411B (zh) * | 2019-11-07 | 2021-09-24 | 江苏理工学院 | 一种多氯甲基取代二氢异喹啉酮化合物的合成方法 |
CN114644655A (zh) * | 2022-04-19 | 2022-06-21 | 湖南农业大学 | 一种光催化磷酰化喹唑啉酮类化合物的制备方法 |
CN114644655B (zh) * | 2022-04-19 | 2023-10-27 | 湖南农业大学 | 一种光催化磷酰化喹唑啉酮类化合物的制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN111675662B (zh) | 一种2-三氟甲基取代的喹唑啉酮化合物的制备方法 | |
WO2018152950A1 (zh) | 一种布瓦西坦的新的制备方法 | |
CN110041367A (zh) | 光催化合成膦酰化二氢异喹啉酮类化合物 | |
CN107382856A (zh) | 新型多取代异喹啉衍生物及其合成方法 | |
CN113929605B (zh) | 一种邻位磺酰化芳胺化合物及其合成方法 | |
CN110003274A (zh) | 膦酰化二氢异喹啉酮类化合物及其制备方法 | |
CN114292231B (zh) | 一种2-甲基-8-取代基-喹啉及其制备方法 | |
CN105481867B (zh) | 三步接力催化构建手性螺环氧化吲哚及其合成方法和应用 | |
CN102863399B (zh) | 一种靛红酸酐衍生物的合成方法 | |
CN104844593A (zh) | 一种阿哌沙班药物中间体的合成方法 | |
CN112321467A (zh) | 一种(2s,3r)-对甲砜基苯丝氨酸乙酯的制备方法 | |
CN109705006A (zh) | 一种二芳基硫醚类化合物及其制备方法 | |
CN105884807A (zh) | 硼酸频那醇酯衍生物的制备方法、硫代乙酸盐化合物的制备方法 | |
CN107383097A (zh) | N‑苯基‑3‑苯亚甲基异吲哚‑1‑酮的膦酰化衍生物的制备方法 | |
CN102127014A (zh) | 一种氮杂菲酮化合物及其制备方法 | |
Tang et al. | Recent Advances on Benzofuranones: Synthesis and Transformation via C–H Functionalization | |
CN114716319B (zh) | 一种联芳氧基烯酸酯类化合物的合成方法 | |
CN111499622A (zh) | 一种治疗胆管癌的药物的制备方法 | |
CN113754597B (zh) | 一种含直链烯烃的二苯甲基哌嗪类化合物及其制备方法 | |
CN108794395B (zh) | 一种2-喹啉酮类化合物的制备方法 | |
KR101404616B1 (ko) | 키랄 감마-플루오로 케톤 화합물의 제조방법 | |
CN113929637B (zh) | 一种含硫基二氢异恶唑类化合物及其合成方法 | |
CN109803954B (zh) | 尼达尼布及其中间体的制备方法 | |
CN107739322B (zh) | 一种磺酰胺类化合物的合成方法 | |
CN108558862B (zh) | 一种抗白血病癌细胞活性分子的合成方法和中间体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190723 |