CN113788812B - 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 - Google Patents
一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 Download PDFInfo
- Publication number
- CN113788812B CN113788812B CN202111202594.0A CN202111202594A CN113788812B CN 113788812 B CN113788812 B CN 113788812B CN 202111202594 A CN202111202594 A CN 202111202594A CN 113788812 B CN113788812 B CN 113788812B
- Authority
- CN
- China
- Prior art keywords
- reaction
- phenylacetylene
- dihydrothiophene
- allyl mercaptan
- znin
- 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.)
- Active
Links
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 title claims abstract description 42
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 17
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 239000011941 photocatalyst Substances 0.000 claims abstract description 10
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- -1 dihydrothiophene compound Chemical class 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 4
- 238000007664 blowing Methods 0.000 claims description 3
- 238000007872 degassing Methods 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 230000001699 photocatalysis Effects 0.000 abstract description 6
- 238000007146 photocatalysis Methods 0.000 abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021617 Indium monochloride Inorganic materials 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YRCWQPVGYLYSOX-UHFFFAOYSA-N synephrine Chemical compound CNCC(O)C1=CC=C(O)C=C1 YRCWQPVGYLYSOX-UHFFFAOYSA-N 0.000 description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 1
- ZNTJVJSUNSUMPP-UHFFFAOYSA-N 1-ethyl-4-ethynylbenzene Chemical group CCC1=CC=C(C#C)C=C1 ZNTJVJSUNSUMPP-UHFFFAOYSA-N 0.000 description 1
- JXYITCJMBRETQX-UHFFFAOYSA-N 4-ethynylaniline Chemical group NC1=CC=C(C#C)C=C1 JXYITCJMBRETQX-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 229960002866 duloxetine Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229960003684 oxedrine Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000005450 thionucleoside Substances 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229960000257 tiotropium bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Abstract
本发明公开了一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法，属于有机化学及光催化领域。该方法以ZnIn2S4作为光催化剂，在可见光的条件下，在N2气氛中通过苯乙炔与烯丙基硫醇的发生环化反应生成二氢噻吩，产率良好，同时制备该催化剂的方法简便易行，后处理过程中产物与催化剂易分离。
Description
技术领域
本发明属于有机化学及光催化领域，具体涉及到一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法。
背景技术
噻吩是五元含硫杂环化合物，最初是从煤焦油中发现的。噻吩及其衍生物具有广泛的生物或药理活性。杂环化合物二氢噻吩广泛分布于许多天然产物中，是一类具有生物活性的化合物，具有重要的药用价值和生物活性。另一方面，二氢噻吩也是许多化合物（包括噻吩，硫代核苷衍生物和青霉素）的重要合成前驱体。目前，含有噻吩母核结构的药物已超过两百多种。而且在研究中发现，噻吩结构对有些药物活性的影响远远高于苯环结构。一些新的临床药物，如治疗老年男性骨质疏松症的药物雷诺昔吩，用于治疗抑郁症和综合焦虑失调症的度洛西汀，俗称欣百达药物，长效吸入型支气管扩张药噻托溴铵，以及治疗青光眼的药物可速普特都是含有噻吩结构单元的药物。此外，噻吩还可用来合成功能性材料和食用香料等物质。因此，探究一种绿色、高效的二氢噻吩合成方法显得尤为重要且颇有意义。
发明内容
本发明的目的在于提供一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法，。该方法以ZnIn2S4作为光催化剂，在可见光的条件下，在N2气氛中通过苯乙炔与烯丙基硫醇的环化反应生成二氢噻吩，产率良好，同时制备该催化剂的方法简便易行，后处理过程中产物与催化剂易分离。
为实现上述目的，本发明采用如下技术方案：
以ZnIn2S4作为光催化剂，在可见光的条件下，在N2气氛中通过苯乙炔与烯丙基硫醇的环化反应生成二氢噻吩。具体步骤为：将10 mg催化剂ZnIn2S4、0.1 mmol苯乙炔和0.1mmol烯丙基硫醇加入装有溶剂甲醇（CH3OH, 2 ml）的Schlenk反应管，经过三次脱气、鼓气操作，使反应气氛为N2。在室温条件下，从反应管底部利用65 mW/cm2的LED灯照射15 h，反应过程中保持持续搅拌的操作。反应结束后，取出反应液并通过多孔膜（直径为20 μm）过滤，得到的滤液通过配备HP-5毛细管柱的GC-MS（Agilent 7890B-5977A）和GC-FID（Shimadzu2014）进行分析，并用LC-MS（Agilent X Series 2）辅助分析产物的组成。
上述所用光催化剂ZnIn2S4的制备方法，包括以下步骤：
通过双溶剂法制备催化剂ZnIn2S4，将前驱物ZnCl2（1 mmol）、InCl3·4H2O（2 mmol）和硫代乙酰胺（TAA, 4 mmol）按照顺序分别加入30 ml乙二醇（EG）和30 ml N,N-二甲基甲酰胺（DMF）的混合溶液中，并超声直至固体在溶液中分散均匀，持续搅拌1小时左右，再将混合液全部转移至100 ml 聚四氟乙烯反应釜中。密封后将反应釜放入烘箱中，反应温度为180 ℃，反应24 h，自然冷却至室温后将产物取出，分别经无水乙醇和去离子水离心洗涤3次，烘干，得到亮黄色产物ZnIn2S4。
本发明的显著优点在于：
（1）本发明在温和条件下实现了光催化环化反应合成二氢噻吩，烯丙基硫醇在ZnIn2S4光催化下生成相应的巯基自由基，在温和条件下与苯乙炔进行成环反应，生成相应的二氢噻吩产物，具有实际应用价值。
（2）本发明光催化剂的制备方法简单易行，价格低廉且没有金属残留，具有后处理产物与催化剂易分离的特点，催化剂可以重复利用。
具体实施方式
下面结合实施例对本发明进一步详细说明，需要指出的是，以下所述实施例旨在便于对本发明的理解，而对其不起任何限定作用。
光催化剂ZnIn2S4催化苯乙炔与烯丙基硫醇环化反应的活性测试在N2气氛下进行，反应温度为室温。具体步骤为：将10 mg催化剂ZnIn2S4、0.1 mmol苯乙炔和0.1 mmol烯丙基硫醇加入装有溶剂甲醇（CH3OH, 2 ml）的Schlenk反应管，经过三次脱气、鼓气操作，使反应气氛为N2。在室温条件下，从反应管底部利用65 mW/cm2的LED灯照射15 h，反应过程中保持持续搅拌的操作。反应结束后，取出反应液并通过多孔膜（直径为20 μm）过滤，得到的滤液通过配备HP-5毛细管柱的GC-MS（Agilent 7890B-5977A）和GC-FID（Shimadzu 2014）进行分析，并用LC-MS（Agilent X Series 2）辅助分析产物的组成。
光催化剂的具体制备步骤如下：
将前驱物ZnCl2（1 mmol）、InCl3·4H2O（2 mmol）和硫代乙酰胺（TAA, 4 mmol）按照顺序分别加入30 ml乙二醇（EG）和30 ml N,N-二甲基甲酰胺（DMF）的混合溶液中，并超声直至固体在溶液中分散均匀，持续搅拌1小时左右，再将混合液全部转移至100 ml 聚四氟乙烯反应釜中。密封后将反应釜放入烘箱中，反应温度为180 ℃，反应24 h，自然冷却至室温后将产物取出，分别经无水乙醇和去离子水离心洗涤3次，烘干，得到亮黄色产物ZnIn2S4。
实施例1
以10 mg ZnIn2S4作催化剂，苯乙炔和烯丙硫醇作为底物，甲醇作溶剂，在N2气氛保护下，使用65 mW/cm2LED灯光照15 h，底物苯乙炔的转化率为76.6%，二氢噻吩的产率为50.1%。在没有光照射和不加光催化剂的情况下，底物并没有发生转化，可以得出光照和光催化剂是本反应的必要条件。
表1 光催化苯乙炔和烯丙基硫醇成环反应条件探索
实施例2
在甲醇为溶剂、ZnIn2S4作催化剂、N2气氛下，利用LED灯光照15 h，选用不同取代基的炔烃进行底物拓展反应，当炔烃为苯环上连有不同取代基的苯乙炔时，该成环反应可以顺利进行（序号1-4），73.3%的对甲基苯乙炔被转化，生成49.1%的3-对甲基苯基-4-甲基-4,5-二氢噻吩（序号1），对乙基苯乙炔以48.4%的产率生成3-对乙基苯基-4-甲基-4,5-二氢噻吩（序号2），对氨基苯乙炔以42.3%的产率生成3-对氨基苯基-4-甲基-4,5-二氢噻吩（序号3），对硝基苯乙炔则以40.6%的产率生成3-对硝基苯基-4-甲基-4,5-二氢噻吩（序号4），从上述结果可以发现电子效应对反应的影响并不明显，说明本反应底物适应性良好。
表2 光催化苯乙炔和烯丙基硫醇成环反应的底物适用性探究
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。
Claims (1)
1.一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩类化合物的方法，其特征在于：在可见光条件下，以ZnIn2S4作为光催化剂，在N2气氛中实现苯乙炔与烯丙基硫醇的环化反应生成二氢噻吩类化合物；所述方法具体包括以下步骤：
（1）将催化剂ZnIn2S4、苯乙炔和烯丙基硫醇加入装有甲醇的Schlenk反应管，经过三次脱气、鼓气操作，使反应气氛为N2，
（2）在室温条件下，从反应管底部利用65 mW/cm2的LED灯照射15 h，反应过程中保持持续搅拌的操作；反应结束后，取出反应液，经分离提纯得到二氢噻吩类化合物；所述二氢噻吩类化合物的结构式如下：
。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111202594.0A CN113788812B (zh) | 2021-10-15 | 2021-10-15 | 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111202594.0A CN113788812B (zh) | 2021-10-15 | 2021-10-15 | 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113788812A CN113788812A (zh) | 2021-12-14 |
| CN113788812B true CN113788812B (zh) | 2023-03-14 |
Family
ID=79184908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111202594.0A Active CN113788812B (zh) | 2021-10-15 | 2021-10-15 | 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113788812B (zh) |
-
2021
- 2021-10-15 CN CN202111202594.0A patent/CN113788812B/zh active Active
Non-Patent Citations (3)
| Title |
|---|
| Efficient visible light initiated hydrothiolations of alkenes/alkynes over Ir2S3/ZnIn2S4: Role of Ir2S3;Xinglin Wang等;《催化学报》;20210305;第42卷(第3期);第409-416页 * |
| Et3B Induced Radical Addition of Thiols to Acetylenes;Yoshifumi ICHINOSE等;《CHEMISTRY LETTERS》;19871231;第1647-1650页 * |
| Free-Radical Addition of Alkanethiols to Alkynes. Rearrangements of the Intermediate β-Thiovinyl Radicals;Luisa Benati等;《J. Org. Chem.》;19941231;第59卷(第10期);第2818-2823页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113788812A (zh) | 2021-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108329256B (zh) | 一种多取代含硫或硒的苯并[c,d]吲哚类化合物的合成方法 | |
| CN108017613B (zh) | 钌催化杂环芳酮与二苯乙炔反应制备多芳取代萘衍生物的方法 | |
| CN110590819B (zh) | 有机硼化合物的制备方法以及β-羟基有机硼化合物的制备方法 | |
| CN110386885B (zh) | 一种可见光促进β-羰基砜化合物的制备方法 | |
| CN109180625B (zh) | 一种硒代黄酮类化合物的制备方法 | |
| CN105175328A (zh) | 一种利用芳香胺、芳香醛、酮合成喹啉衍生物的方法 | |
| CN110183373B (zh) | 一种光学活性1-芳基吲哚衍生物及其制备方法和应用 | |
| CN107513003A (zh) | 一种1,4‑二取代‑1,3‑丁二炔的制备方法 | |
| CN108440375B (zh) | 以二硫醚为硫源的3-巯基吲哚类化合物的催化氧化合成方法 | |
| CN113788812B (zh) | 一种由苯乙炔与烯丙基硫醇环化生成二氢噻吩的方法 | |
| CN112724058B (zh) | 一种可见光促进β-羟基硒醚化合物的合成方法 | |
| CN109053510A (zh) | 一种可见光催化的三氟甲基取代的硫烯酮衍生物的合成方法 | |
| CN110862368B (zh) | 一种苯并香豆素类化合物的光催化氧化合成方法 | |
| CN111689911A (zh) | 一种区域选择性合成7-芳硒基喹喔啉酮衍生物的方法 | |
| CN110590788A (zh) | 一种2-酰基-9H-吡咯并[1,2-a]吲哚类化合物的合成方法 | |
| CN115322100A (zh) | 一种δ,ε-烯基酮类化合物及其制备方法与应用 | |
| CN110317170B (zh) | 一种3-菲啶基甲酸丙酯类化合物的绿色合成方法 | |
| CN109232564B (zh) | 一种分子碘促进的一锅法合成3位硫基取代咪唑并[1,2-a]吡啶化合物的方法 | |
| CN109851599B (zh) | 一种2-氨基苯并呋喃化合物的制备方法 | |
| You et al. | Catalytic Enantioselective Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones and Vinyl Selenides | |
| CN108276420B (zh) | 一种8,13-二氢苯并[5,6]色烯并[2,3-b]吲哚类化合物及其合成方法 | |
| CN105693778A (zh) | N-甲氧基甲酰胺导向合成二茂铁并吡啶酮衍生物的方法 | |
| CN109384753B (zh) | 一种2-苯基-3-甲基苯并呋喃类化合物的合成方法 | |
| CN107445835B (zh) | 一种1,2-二氢环丁烯并[a]萘衍生物及其前体的合成方法 | |
| CN110668987A (zh) | 一种可见光促进二硫代氨基甲酸酯类化合物的合成方法及应用 |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |