CN115197122A - Preparation method of N heteroatom multi-condensed ring - Google Patents
Preparation method of N heteroatom multi-condensed ring Download PDFInfo
- Publication number
- CN115197122A CN115197122A CN202210574596.0A CN202210574596A CN115197122A CN 115197122 A CN115197122 A CN 115197122A CN 202210574596 A CN202210574596 A CN 202210574596A CN 115197122 A CN115197122 A CN 115197122A
- Authority
- CN
- China
- Prior art keywords
- reaction
- heteroatom
- added
- rhodium
- catalyst
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 title claims description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000010189 synthetic method Methods 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000010898 silica gel chromatography Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- YNWSXIWHOSSPCO-UHFFFAOYSA-N rhodium(2+) Chemical compound [Rh+2] YNWSXIWHOSSPCO-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- -1 DM-SEGPHOS Chemical compound 0.000 claims description 2
- RZZDRSHFIVOQAF-UHFFFAOYSA-N [4-(5-diphenylphosphanyl-1,3-benzodioxol-4-yl)-1,3-benzodioxol-5-yl]-diphenylphosphane Chemical compound C=12OCOC2=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1C1=C2OCOC2=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RZZDRSHFIVOQAF-UHFFFAOYSA-N 0.000 claims description 2
- ZNORAFJUESSLTM-UHFFFAOYSA-N [4-[5-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphanyl-1,3-benzodioxol-4-yl]-1,3-benzodioxol-5-yl]-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphane Chemical compound C1=C(C(C)(C)C)C(OC)=C(C(C)(C)C)C=C1P(C=1C(=C2OCOC2=CC=1)C=1C(=CC=C2OCOC2=1)P(C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C=1C=C(C(OC)=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC(C(C)(C)C)=C(OC)C(C(C)(C)C)=C1 ZNORAFJUESSLTM-UHFFFAOYSA-N 0.000 claims description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims 6
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 2
- 229910052703 rhodium Inorganic materials 0.000 claims 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
- GDMCOFXEPNHXJT-UHFFFAOYSA-N [5-(6-diphenylphosphanyl-2,3-dihydro-1,4-benzodioxin-5-yl)-2,3-dihydro-1,4-benzodioxin-6-yl]-diphenylphosphane Chemical compound O1CCOC(C=2C=3C=4OCCOC=4C=CC=3P(C=3C=CC=CC=3)C=3C=CC=CC=3)=C1C=CC=2P(C=1C=CC=CC=1)C1=CC=CC=C1 GDMCOFXEPNHXJT-UHFFFAOYSA-N 0.000 claims 1
- MQHNKCZKNAJROC-UHFFFAOYSA-N dipropyl phthalate Chemical compound CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 claims 1
- SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 claims 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 abstract description 4
- 230000004071 biological effect Effects 0.000 abstract description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
- C07D209/92—Naphthostyrils
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a synthetic method of a nitrogen heteroatom polycyclic fused ring, wherein the synthetic route starts from known benzocyclobutene ketene A, gram-scale preparation can be realized, the yield can reach more than 90%, the reaction can be operated in a conventional environment, no special equipment of a glove box is needed, the synthetic route provided by the invention provides a simpler and more effective way for the synthesis of compounds with biological activity, the yield is high, and the large-scale preparation can be realized.
Description
Technical Field
The invention relates to a preparation method of N heteroatom multi-condensed rings.
Background
Different types of aza-multi condensed rings are constructed by utilizing the ring tension of the four-membered ring in the benzocyclobutene and activating through a carbon-carbon bond, wherein the benzocyclobutene with different substituents can obtain various types of products, such as spiro, fused ring and other various types of compounds under appropriate conditions through the activation of the carbon-carbon bond. The current published papers need to use a solvent after anhydrous treatment, and the reaction can be completed only by adding a reagent under the protection of an all-inert gas, special equipment is required, and the requirements of the reagent on oxygen and water are high.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of N heteroatom multi-condensed rings, which can prepare the compounds under the conventional conditions, avoid special equipment such as a glove box, can complete the operation under the conventional conditions, has high yield and can be applied to industrial production.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a preparation method of N heteroatom multi-condensed rings comprises the following steps:
(1) Adding a substrate A, a rhodium (II) catalyst, a ligand and a solvent into a branch mouth bottle under the protection of nitrogen, heating to 130-170 ℃, reacting for 24-96 h, cooling to room temperature, concentrating a reaction solution under reduced pressure, filtering, and performing silica gel column chromatography to obtain a corresponding target product B.
The specific reaction process is as follows:
in the scheme, A in the step (1) is benzocyclobutene ketene containing a double bond structure.
In the scheme, the amount of the rhodium (II) catalyst used in the step (1) is 2.5-5% times of the amount of the substrate substance.
In the scheme, in the step (1), the amount of the ligand used is 3% -6% times of the amount of the substrate substance.
In the above scheme, in the step (1), the solvent used in the reaction is one of tetrahydrofuran, 1,4-dioxane, toluene, xylene, and mesitylene.
In the scheme, in the step (1), after the reaction is completed, the reaction solution is cooled to room temperature, and the target product is obtained after the reaction solution is subjected to silica gel column chromatography after being subjected to reduced pressure concentration.
Through the technical scheme, the preparation method of the N heteroatom multi-condensed ring has high applicability, can be widely applied to preparation of different substituted multi-condensed ring compounds, and is based on compound research, the benzo four-membered ring compound containing cyano, phenyl and halogen substitution on a benzene ring is a basic structural element of a plurality of active compounds. Therefore, the synthetic route provided by the invention provides a simpler and more effective way for synthesizing the compounds with biological activity, has high yield and can be produced in a large scale.
Detailed Description
The technical scheme in the embodiment of the invention is clearly and completely described below with reference to the accompanying drawings.
The invention provides a method for synthesizing N heteroatom multi-condensed rings, which comprises the following specific embodiments:
the first embodiment is as follows:
adding substrate A (1 mmol), rh to a branched bottle under nitrogen protection 2 (OAc) 4 (0.02 mmol), BINAP (0.03 mmol) or DTBM-SEGPHOS (0.03 mmol), tetrahydrofuran (10 ml) are heated to 150 ℃ for 24h, cooled to room temperature,
after the reaction solution is decompressed and concentrated, the corresponding target product is obtained by silica gel column chromatography with the yield of 94 percent.
The second embodiment:
adding substrate A (1 mmol), rh to a flask under nitrogen protection 2 (OCt) 4 (0.02 mmol), synphos (0.03 mmol) or SEGPHOS, ligand and toluene (10 ml) are heated to 150 ℃, reacted for 24h, cooled to room temperature,
after the reaction solution is decompressed and concentrated, the corresponding target product is obtained by silica gel column chromatography, and the yield is 90%.
Example three:
adding substrate A (1 mmol), rh to a branched bottle under nitrogen protection 2 (S-DOSP) 4 (0.02 mmol), dppe/dppb/dppf (0.03 mmol) and 1,4-dioxane (10 ml) are heated to 130 ℃, reacted for 24h, cooled to room temperature, and subjected to reduced pressure concentration and then treated bySilica gel column chromatography is carried out to obtain the corresponding target product with the yield of 87 percent.
Example four:
adding substrate A (1 mmol), rh to a flask under nitrogen protection 2 (S-DOSP) 4 (0.02 mmol), dppe/dppb/dppf (0.03 mmol) and dimethylbenzene (10 ml), the reaction is carried out for 48h after being heated to 170 ℃, the reaction solution is cooled to room temperature, and after the reaction solution is decompressed and concentrated, the corresponding target product is obtained by silica gel column chromatography with the yield of 87%.
Example five:
adding substrate A (1 mmol), rh to a flask under nitrogen protection 2 (esp) 4 (0.05 mmol) xphos (0.06 mmol) and mesitylene (10 ml), heating to 170 ℃, reacting for 96h, cooling to room temperature, concentrating the reaction solution under reduced pressure, and performing silica gel column chromatography to obtain the corresponding target product with the yield of 90%.
Claims (5)
1. A synthetic method of N heteroatom multi-condensed rings is characterized by comprising the following steps:
adding a substrate, a rhodium (II) catalyst, a ligand and a solvent into a reaction bottle under the protection of nitrogen, heating to 130-170 ℃, reacting for 24-96 h, cooling to room temperature, filtering after the reaction liquid is subjected to reduced pressure concentration, and performing silica gel column chromatography to obtain a corresponding N heteroatom multi-element condensed ring compound;
the specific reaction process is as follows:
2. the method for synthesizing N heteroatom multi-element condensed rings according to claim 1, characterized in that a substrate, a rhodium (II) catalyst, a ligand and a solvent are added into a reaction bottle under the protection of nitrogen, the reaction is carried out at 130 to 170 ℃, the reaction is carried out for 24 to 96 hours, the reaction solution is cooled to room temperature, the reaction solution is decompressed and concentrated, the dosage of the added rhodium catalyst is 2.5 to 5 percent, and the added amount of the ligand is 3 to 6 percent, wherein the rhodium catalyst is added into the corresponding N heteroatom multi-element condensed ring compound obtained by filtering and silica gel column chromatography.
3. The method for synthesizing N heteroatom polybasic condensed rings according to claim 1, wherein a substrate, a rhodium (II) catalyst, a ligand and a solvent are added into a reaction bottle under the protection of nitrogen, the reaction is carried out at 130 to 170 ℃, the reaction is carried out for 24 to 96 hours, the reaction solution is cooled to room temperature, the reaction solution is subjected to reduced pressure concentration, and the rhodium (II) catalyst added into the corresponding N heteroatom polybasic condensed ring compound obtained by filtering and silica gel column chromatography is: rhodium acetate and Rh 2 (S-DOSP) 4 、Rh 2 (R-DOSP) 4 、Rh 2 (Oct) 4 、Rh 2 (S-DOSP) 4。
4. The preparation method of the N heteroatom polybasic condensed rings according to claim 1, wherein a substrate, a rhodium (II) catalyst, a ligand and a solvent are added into a reaction bottle under the protection of nitrogen, the reaction is carried out at 130 to 170 ℃, the reaction is carried out for 24 to 96 hours, the reaction solution is cooled to room temperature, the reaction solution is subjected to reduced pressure concentration, and the added ligand in the corresponding N heteroatom polybasic condensed ring compound obtained by filtering and silica gel column chromatography is: BINAP, SYNPHOS, SEGPHOS, DM-SEGPHOS, DTBM-SEGPHOS, XPHOS, DPPB, DPPP, DPP penta, DDPF.
5. The preparation method of the N heteroatom polybasic condensed rings according to claim 1, wherein a substrate, a rhodium (II) catalyst, a ligand and a solvent are added into a reaction bottle under the protection of nitrogen, the reaction is carried out for 24 to 96 hours after heating to 130 to 170 ℃, the reaction is cooled to room temperature, reaction liquid is decompressed and concentrated, and the solvent added into the corresponding N heteroatom polybasic condensed ring compound obtained by filtering and silica gel column chromatography is: 1,4-dioxane, toluene, tetrahydrofuran, xylene, trimethylbenzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210574596.0A CN115197122A (en) | 2022-05-25 | 2022-05-25 | Preparation method of N heteroatom multi-condensed ring |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210574596.0A CN115197122A (en) | 2022-05-25 | 2022-05-25 | Preparation method of N heteroatom multi-condensed ring |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115197122A true CN115197122A (en) | 2022-10-18 |
Family
ID=83576704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210574596.0A Pending CN115197122A (en) | 2022-05-25 | 2022-05-25 | Preparation method of N heteroatom multi-condensed ring |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115197122A (en) |
-
2022
- 2022-05-25 CN CN202210574596.0A patent/CN115197122A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| BO QIU等: "Catalytic Enantioselective Synthesis of 3, 4-Polyfused Oxindoles with Quaternary All-Carbon Stereocenters: A Rh-Catalyzed C−C Activation Approach", 《ORGANIC LETTERS》, vol. 20, no. 23, pages 7691 * |
| 李晓彤: "Rh催化的C-C键活化应用于麦角生物碱的全合成", 《中国优秀硕士学位论文全文数据库》, pages 1 - 103 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Asao et al. | Nanoporous gold-catalyzed [4+ 2] benzannulation between ortho-alkynylbenzaldehydes and alkynes | |
| Ramulu et al. | Superacid-Promoted Dual C–C Bond Formation by Friedel–Crafts Alkylation and Acylation of Ethyl Cinnamates: Synthesis of Indanones | |
| CN108178770A (en) | A kind of method for synthesizing alpha-amido boron compound | |
| JPS62178594A (en) | Novel phosphine compound | |
| CN112358443B (en) | Pyridine compound and preparation method thereof | |
| CN115197122A (en) | Preparation method of N heteroatom multi-condensed ring | |
| CN104876850A (en) | Isoindolinone derivative synthesis method | |
| Tsutsumi et al. | The practical preparation of chiral N-sulfonyl oxaziridines via catalytic asymmetric payne oxidation | |
| CN112321487A (en) | Polysubstituted isoindoline compound and preparation method thereof | |
| Gelat et al. | Total synthesis of (–)-herbaric acid through organocatalyzed asymmetric halolactonization of acrylate-type benzoic acids | |
| CN106905358B (en) | Preparation of vitamin D3Process for preparing analogue intermediates | |
| Ichikawa et al. | Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products | |
| Ghosh et al. | Hopping of Palladium: Access to Original Polycyclic Structures Containing Three-, Four-, Five-and Six-Membered Rings | |
| CN106588984B (en) | A kind of preparation method of 6- phosphoryls substitution phenanthridines analog derivative | |
| CN113717135A (en) | Synthesis method of carbonyl substituted benzodihydropyran and benzodihydropyran compound | |
| Chen et al. | An easy one-pot synthesis of tetrasubstituted 3-alkynylpyrroles via multicomponent coupling reaction | |
| Yagita et al. | Toward the Total Synthesis of Schinortriterpenoids: Construction of the All-cis-Substituted Cyclopropane Unit | |
| Wang et al. | Synthesis of S (IV)‐Stereogenic Chiral Thio‐Oxazolidinones via Palladium‐Catalyzed Asymmetric [3+ 2] Annulations | |
| Li et al. | Further Insight into the Photochemical Behavior of Aromatic γ, δ-Epoxy Ketones: A New Approach for Synthesis of 4-Methyleneisochromanols | |
| CN108047196B (en) | Method for catalytically synthesizing 2, 5-dihydrothiophene compound containing chiral quaternary carbon | |
| CN108658802A (en) | A kind of bis- [N, O] the ring palladium complexes of chirality and its synthetic method | |
| CN115385818B (en) | Paracetamol impurity and preparation method thereof | |
| CN113563355B (en) | C-H activation product on isatin skeleton and preparation method and application thereof | |
| CN116354806B (en) | Phosphine catalysis preparation method of full-carbon quaternary carbon cyclopentenone derivative | |
| Arcadi et al. | 4-Aryl-and 4-vinyl-2, 2-dialkyl-3-chromenes from tertiary 3-(o-bromophenyl) propynols via a palladium-catalyzed hydroarylation/hydrovinylation-cyclization sequence |
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 |