CN117552023A - 一种含硫氰基磺酰胺类化合物的制备方法 - Google Patents
一种含硫氰基磺酰胺类化合物的制备方法 Download PDFInfo
- Publication number
- CN117552023A CN117552023A CN202311493392.5A CN202311493392A CN117552023A CN 117552023 A CN117552023 A CN 117552023A CN 202311493392 A CN202311493392 A CN 202311493392A CN 117552023 A CN117552023 A CN 117552023A
- Authority
- CN
- China
- Prior art keywords
- sulfur
- sulfonamide
- containing cyano
- preparation
- reaction
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 17
- -1 cyano sulfonamide compound Chemical class 0.000 title claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 17
- 239000011593 sulfur Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 3
- XYMVZPOXZCDCNP-UHFFFAOYSA-N sulfamoyl cyanide Chemical class NS(=O)(=O)C#N XYMVZPOXZCDCNP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000003792 electrolyte Substances 0.000 abstract 1
- 238000010898 silica gel chromatography Methods 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SMFNIURNBQXLJX-UHFFFAOYSA-N FNS(=O)=O Chemical compound FNS(=O)=O SMFNIURNBQXLJX-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125796 compound 3d Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MUTCAPXLKRYEPR-ITWZMISCSA-N methyl (e,3r,5s)-7-[4-bromo-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyhept-6-enoate Chemical compound COC(=O)C[C@H](O)C[C@H](O)\C=C\N1C(C(C)C)=C(Br)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 MUTCAPXLKRYEPR-ITWZMISCSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明公开了属于有机合成技术领域的一种含硫氰基磺酰胺类化合物的制备方法。所述方法为：向反应器中加入磺酰胺、异硫氰酸三甲基硅酯、电解质、溶剂，在恒电流的作用下反应，反应完毕后，用硅胶柱层析分离得到纯的目标产物。本发明所提供的含硫氰基磺酰胺类化合物的制备方法具有原料易得、操作简单、反应条件温和、官能团普适性好等特点。其反应方程式如下：
Description
技术领域
本发明属于有机合成技术领域，具体涉及一种电催化含硫氰基磺酰胺类化合物的制备方法。
背景技术
硫氰酸酯是天然产物和生物活性化合物中常见的官能团，具有抗菌、抗癌(J.Am.Chem.Soc.2005,127,15004)、杀虫(J.Med.Chem.2002,45,3984)等生物活性。硫氰酸酯也是合成含硫和含氮化合物的重要结构单元。因此，发展一种绿色、高效合成含硫氰基磺酰胺类化合物的新方法具有重要意义。
含硫氰基磺酰胺类化合物的制备方法有：
张洪伟课题组(Adv.Synth.Catal.2020,362,3851)和刘峰课题组(Org.Chem.Front.2021,8,249)利用N-氟代磺酰胺做原料，在铜催化下实现了含硫氰基磺酰胺类化合物的制备。
利用上述方法合成含硫氰基磺酰胺类化合物，具有明显的缺点和不足：1)底物需要预官能团化；2)需要使用催化剂和配体；3)反应条件剧烈。
发明内容
为了克服上述现有技术的不足，本发明提供了一种电催化含硫氰基磺酰胺类化合物的制备方法。
一种含硫氰基磺酰胺类化合物的制备方法，所述含硫氰基磺酰胺类化合物具有式Ⅰ所示的结构：
式Ⅰ中，当R1取代基为甲基时，R2取代基选自氢原子、甲基、正丁基、苯基；当R2取代基为甲基时，R1取代基选自氢原子、溴、甲氧基、三氟甲基；其特征在于，向反应器中加入0.2mmol磺酰胺、0.3mmol异硫氰酸三甲基硅酯、0.1mmol四丁基醋酸铵、0.4mmol甲酸，5mL六氟异丙醇作溶剂，在恒电流条件下室温反应，反应方程式如下：
本发明的有益效果为：本发明提供的含硫氰基磺酰胺类化合物的合成方法科学合理，建立了一种电催化制备含硫氰基磺酰胺类化合物的新方法；该方法具有原料易得、操作简单、反应条件温和、官能团普适性好等特点。
附图说明
图1为实施例1制备的化合物3a的NMR图谱；
图2为实施例4制备的化合物3d的NMR图谱；
图3为实施例8制备的化合物3h的NMR图谱。
具体实施方式
下面结合附图和具体的实施例对本发明进一步详细的说明：
下述实施例中所述试验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1
含硫氰基磺酰胺化合物3a的制备
在一个10mL的三口瓶中，碳板(1cm×1.5cm×0.3cm)作阳极和铂片(1cm×1cm×0.1mm)作阴极,1a(48mg，0.2mmol),TMSNCS(39mg，0.3mmol)，HCOOH(18mg，0.4mmol),TBAOAc(32mg，0.1mmol)和HFIP(5mL)。在室温下，在氮气保护下、以10mA恒定电流下电解4.5h。反应完成后，将混合物在减压下浓缩。通过硅胶快速色谱法，使用石油醚和乙酸乙酯作为洗脱液，得到产物3a，产率63％。
谱图解析数据3a:
1H NMR(500MHz,CDCl3)δ7.74(d,J＝7.9Hz,2H),7.33(d,J＝7.9Hz,2H),4.48(t,J＝6.5Hz,1H),3.23-3.16(m,1H),2.98(q,J＝6.6Hz,2H),2.44(s,3H),1.79-1.71(m,2H),1.69-1.61(m,2H),1.48(d,J＝6.7Hz,3H).
13C NMR(125MHz,CDCl3)δ143.8,136.9,130.0,127.2,111.1,45.2,42.6,34.0,27.3,22.1,21.7.
实施例2
用1b代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3b:
1H NMR(500MHz,CDCl3)δ7.72(d,J＝8.6Hz,2H),7.67(d,J＝8.6Hz,2H),4.85(t,J＝6.3Hz,1H),3.24-3.17(m,1H),2.98(q,J＝6.6Hz,2H),1.77-1.72(m,2H),1.68-1.60(m,2H),1.49(d,J＝6.8Hz,3H).
13C NMR(125MHz,CDCl3)δ138.9,132.7,128.7,128.0,111.1,45.1,42.7,34.0,27.3,22.1.
实施例3
用1c代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3c:
1H NMR(500MHz,CDCl3)δ7.79(d,J＝8.9Hz,2H),6.99(d,J＝8.8Hz,2H),4.71(s,1H),3.87(s,3H),3.23-3.16(m,1H),2.95(q,J＝6.6Hz,2H),1.78-1.70(m,2H),1.67-1.62(m,2H),1.48(d,J＝6.8Hz,3H).
13C NMR(125MHz,CDCl3)δ163.2,131.4,129.3,114.5,111.2,55.8,45.2,42.6,34.0,27.2,22.1.
实施例4
用1d代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3d:
1H NMR(500MHz,CDCl3)δ7.86(d,J＝7.2Hz,2H),7.59(t,J＝7.4Hz,1H),7.53(t,J＝7.6Hz,2H),5.04(s,1H),3.22-3.15(m,1H),2.97(t,J＝6.7Hz,2H),1.75-1.69(m,2H),1.66-1.56(m,2H),1.46(d,J＝6.8Hz,3H).
13C NMR(125MHz,CDCl3)δ139.8,132.9,129.4,127.1,111.2,45.1,42.6,33.9,27.2,22.1.
实施例5
用1e代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3e:
1H NMR(500MHz,CDCl3)δ8.00(d,J＝8.1Hz,2H),7.81(d,J＝8.1Hz,2H),4.80(s,1H),3.25-3.18(m,1H),3.07-3.02(m,2H),1.79-1.72(m,2H),1.71-1.62(m,2H),1.49(d,J＝6.7Hz,3H).
13C NMR(125MHz,CDCl3)δ143.7,134.7(q,JC-F＝34.9Hz),127.7,126.6(d,JC-F＝3.9Hz),123.3(q,JC-F＝272.9Hz),111.1,45.1,42.8,34.0,27.4,22.0.
实施例6
用1f代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3f:
1H NMR(500MHz,CDCl3)δ7.74(d,J＝7.9Hz,2H),7.31(d,J＝7.9Hz,2H),4.98(t,J＝6.3Hz,1H),3.00-2.93(m,3H),2.42(s,3H),1.82-1.77(m,1H),1.73-1.57(m,5H),1.48-1.42(m,1H),1.35-1.26(m,3H),0.90(t,J＝7.0Hz,3H).13C NMR(125MHz,CDCl3)δ143.7,136.8,129.9,127.2,111.2,51.2,42.6,35.2,32.4,29.0,27.0,22.3,21.6,14.0.
实施例7
用1g代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3g:
1H NMR(500MHz,CDCl3)δ7.72(d,J＝7.9Hz,2H),7.37-7.23(m,7H),4.83(s,1H),4.26(t,J＝7.8Hz,1H),2.93(q,J＝6.2Hz,2H),2.42(s,3H),2.21-2.09(m,2H),1.55-1.45(m,2H).
13C NMR(125MHz,CDCl3)δ143.7,137.9,136.8,129.9,129.3,129.2,127.5,127.2,111.6,53.0,42.4,32.7,27.6,21.7.
实施例8
用1h代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3h:
1H NMR(500MHz,CDCl3)δ7.74(d,J＝7.6Hz,2H).7.32(d,J＝7.8Hz,2H),4.91(s,1H),2.96(q,J＝6.0Hz,2H),2.90(t,J＝7.0Hz,2H),2.43(s,3H),1.86-1.80(m,2H),1.66-1.60(m,2H).
13C NMR(125MHz,CDCl3)δ143.8,136.8,130.0,127.2,112.2,42.4,33.5,27.9,27.0,21.7.表1
Claims (2)
1.一种含硫氰基磺酰胺类化合物的制备方法，所述含硫氰基磺酰胺类化合物具有式Ⅰ所示的结构：
式Ⅰ中，当R1取代基为甲基时，R2取代基选自氢原子、甲基、正丁基、苯基；当R2取代基为甲基时，R1取代基选自氢原子、溴、甲氧基、三氟甲基；其特征在于，向反应器中加入0.2mmol磺酰胺、0.3mmol异硫氰酸三甲基硅酯、0.1mmol四丁基醋酸铵、0.4mmol甲酸，5mL六氟异丙醇作溶剂，在恒电流条件下反应，反应方程如式II：
2.根据权利要求1所述的制备方法，其特征在于：所述的磺酰胺、异硫氰酸三甲基硅酯、四丁基醋酸铵、甲酸的摩尔比值为1：1.5：0.5：2，溶剂为六氟异丙醇，碳板作阳极，铂片作阴极，恒电流10mA条件下室温进行反应，反应时间为4.5h。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311493392.5A CN117552023A (zh) | 2023-11-10 | 2023-11-10 | 一种含硫氰基磺酰胺类化合物的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311493392.5A CN117552023A (zh) | 2023-11-10 | 2023-11-10 | 一种含硫氰基磺酰胺类化合物的制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117552023A true CN117552023A (zh) | 2024-02-13 |
Family
ID=89819624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311493392.5A Pending CN117552023A (zh) | 2023-11-10 | 2023-11-10 | 一种含硫氰基磺酰胺类化合物的制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117552023A (zh) |
-
2023
- 2023-11-10 CN CN202311493392.5A patent/CN117552023A/zh active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107011145B (zh) | 一种利用可见光催化制备2-碘戊-2-烯-1,4-二酮衍生物的方法 | |
| CN112898192B (zh) | 一种n-酰基吲哚化合物的制备方法 | |
| CN110105305B (zh) | 过渡金属催化的c-h活化/环合合成1,2-苯并噻嗪衍生物的绿色合成方法 | |
| Li et al. | Copper‐Catalyzed Remote Enantioselective Sulfonylation of Yne‐Allylic Esters with Sodium Sulfinates | |
| Guo et al. | Photoredox-catalyzed coupling of aryl sulfonium salts with CO 2 and amines to access O-aryl carbamates | |
| CN110317221B (zh) | 一种多取代炔脒类化合物及其制备方法和应用 | |
| CN108148070B (zh) | 一种呋喃酮并异喹啉酮类化合物的合成方法 | |
| CN111808023B (zh) | 一种制备3-芳基异喹啉衍生物的方法 | |
| CN110878099B (zh) | 一种吡咯[1,2,α]吲哚生物碱衍生物的制备方法 | |
| CN109939737B (zh) | 卡宾钴催化剂、其制备方法及其在催化氢化醛和酮化合物中的应用 | |
| CN111468183A (zh) | 多氟代三芳基手性螺环磷酸催化剂及其制备方法、用途 | |
| CN117552023A (zh) | 一种含硫氰基磺酰胺类化合物的制备方法 | |
| CN110937985A (zh) | 一种姜酮酚的合成方法 | |
| CN113735896B (zh) | 采用单原子钯膦配体制备z-构型-1,2-二锡取代烯烃的方法 | |
| CN112694489B (zh) | N-杂环卡宾铜催化剂的制备方法 | |
| CN111393385B (zh) | 一种苯并噻嗪甲醛衍生物的合成方法 | |
| CN107686460B (zh) | 一种3-取代-3-羟基-2-吲哚酮类化合物的制备方法 | |
| CN111303096A (zh) | 一种多取代1,3-二氢萘并[2,3-c]呋喃衍生物的合成方法 | |
| CN113355684B (zh) | 一种电催化下多取代异喹啉盐衍生物的制备方法 | |
| CN111116450A (zh) | 一种轴手性萘胺方酰胺类有机催化剂及其制备方法和应用 | |
| CN109851548B (zh) | 一种2，3-二取代吲哚类化合物的制备方法 | |
| CN111732541B (zh) | 一种钌催化的c-h活化/环合反应高效合成6-烯基菲啶衍生物的方法 | |
| CN113980055B (zh) | 具联芳骨架的环状膦酰胺类衍生物、合成方法及应用 | |
| CN114426564B (zh) | 一类手性二茂铁膦-1,2-二苯基乙二胺配体及其制备方法和应用 | |
| CN114409714B (zh) | 一种合成1,3-二取代平面手性金属茂化合物的方法 |
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 |