CN106632179B - A kind of synthetic method of Dihydrobenzofuranes class compound - Google Patents

A kind of synthetic method of Dihydrobenzofuranes class compound Download PDF

Info

Publication number
CN106632179B
CN106632179B CN201611225596.0A CN201611225596A CN106632179B CN 106632179 B CN106632179 B CN 106632179B CN 201611225596 A CN201611225596 A CN 201611225596A CN 106632179 B CN106632179 B CN 106632179B
Authority
CN
China
Prior art keywords
class compound
reaction
ddq
dihydrobenzofuranes
dihydrobenzofuranes class
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.)
Expired - Fee Related
Application number
CN201611225596.0A
Other languages
Chinese (zh)
Other versions
CN106632179A (en
Inventor
王云侠
崔娜
赵宇
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Northwest University
Original Assignee
Northwest University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Northwest University filed Critical Northwest University
Priority to CN201611225596.0A priority Critical patent/CN106632179B/en
Publication of CN106632179A publication Critical patent/CN106632179A/en
Application granted granted Critical
Publication of CN106632179B publication Critical patent/CN106632179B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/92—Naphthofurans; Hydrogenated naphthofurans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Furan Compounds (AREA)

Abstract

The invention discloses a kind of synthetic methods of Dihydrobenzofuranes class compound, and phenol derivatives and styrene derivative in the presence of DDQ to that oxidation [3+2] cycloaddition reaction occur and obtain corresponding Dihydrobenzofuranes class compound, R in formula1For C1‑C4Alkoxy or acetamido；R2Selected from hydrogen, C1‑C4Alkyl or halogen；R3, R4Selected from hydrogen, C1‑C4Alkyl or aryl.This method raw material is easy to get, reaction step is few, mild condition, yield are higher, it is easy to operate, be easily industrialized.

Description

A kind of synthetic method of Dihydrobenzofuranes class compound
Technical field
The present invention relates to a kind of synthetic methods of Dihydrobenzofuranes class compound, belong to technical field of organic synthesis.
Background technique
Dihydrobenzofuranes are many with antioxidant activity, the natural products core of antibacterial activity and anti-HIV activity Heart skeleton receives the extensive concern of many organic chemists.Wherein pass through oxidation [3+2] cycloaddition reaction of phenol and alkene The method of Dihydrobenzofuranes skeleton is constructed since raw material is simple and easy to get, and phenol is oxidized easily and gains great popularity.According to oxygen The difference of change condition, which can be roughly divided into two types for oxidation [3+2] cycloaddition reaction of current phenol and alkene reported in the literature: (1) hypervalent iodine reagent, the chloro- 5,6- dicyano -1,4- benzoquinones (DDQ) of 2,3- bis-, single electron metal onidiges, electrochemical oxidation or Na2S2O8Oxidation [3+2] cycloaddition reaction of equal participations.(2) FeCl3·(H2O)6/ DTBP(tert-Butanol peroxide), FeCl3/ DDQ, HOTf(trifluoromethanesulfonic acid)/BQ(benzoquinones), it is seen that light/Ru (bpz)3(PF6)2/(NH4)2S2O8Or visible light/mpg-C3N4/ Catalysis oxidation [3+2] cycloaddition method of the participations such as air.Wherein DDQ has been used for phenol due to oxidation activity with higher In [3+2] oxidation cycloaddition reaction of alkene.
Oxidation [3+2] cycloaddition reaction of DDQ reported in the literature is participated at present phenol and alkene constructs dihydrobenzo furan In the method muttered, FeCl is used3The effect of/DDQ system catalysis oxidation is preferably, the scope of application is relatively wide, yield is also higher, and DDQ Direct oxidation reaction yield is lower, and the substrate scope of application is very narrow.
Summary of the invention
In the case where not having to catalyst, provide it is a kind of simple, efficiently, be easy to industrialized dihydro The novel synthesis of benzofuran compounds.
The present invention realizes that process is as follows:
A kind of synthetic method of Dihydrobenzofuranes class compound, includes the following steps:
Oxidation [3+2] cycloaddition reaction occurs in the presence of DDQ and obtains for phenol derivatives (a) and styrene derivative (b) Corresponding Dihydrobenzofuranes class compound (c),
R in formula1For C1-C4Alkoxy or acetamido；R2Selected from hydrogen, C1-C4Alkyl or halogen；R3, R4Selected from hydrogen, C1-C4Alkyl or aryl.
Above-mentioned reaction solvent for use is acetonitrile, TFE(2,2,2- trifluoroethanols) or HFIP(hexafluoroisopropanol), preferably six Fluorine isopropanol.
In above-mentioned reaction the ratio between molal quantity of phenol derivatives, styrene derivative and DDQ be 1:1.5~2.5:1.0~ 1.5。
Corresponding Dihydrobenzofuranes class compound is obtained with silica gel column purification after above-mentioned cycloaddition reaction.
The present invention is oxidant with DDQ, quickly and efficiently passes through phenol derivative at room temperature in the case where not having to catalyst Oxidation [3+2] cycloaddition reaction of object and styrene derivative, is prepared for a series of Dihydrobenzofuranes class compounds.This method Raw material is easy to get, reaction step is few, mild condition, yield are higher, it is easy to operate, be easily industrialized.
Specific embodiment
The raw materials used in the present invention phenol and styrene derivative can be commercially available by commercial channel.
Embodiment 1
P methoxy phenol (0.15mmol), HFIP 1mL, styrene are sequentially added in dry reaction flask (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as pale yellow oily liquid, yield 88%.1H NMR (400 MHz, CDCl3) δ 7.46-7.30 (m, 5H), 6.83- 6.76 (m, 2H), 6.72 (m, 1H), 5.75 (t, J = 8.8 Hz, 1H), 3.78 (s, 3H), 3.61 (dd,J = 15.7, 9.3 Hz, 1H), 3.21 (dd, J = 15.7, 8.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 154.3, 153.78, 142.0, 128.7, 128.0, 127.5, 125.8, 113.0, 111.2, 109.2, 84.2, 56.1, 38.9. HRMS (ESI+): m/z [M+Na]+ calcd for C15H14NaO2 + 249.0886; found 249.0888。
It is similar to Example 1, the difference is that solvent HFIP is replaced using MeCN, yield 12%.
It is similar to Example 1, the difference is that solvent HFIP is replaced using TFE, yield 27%.
Embodiment 2
It is sequentially added in dry reaction flask to thanatol (0.15mmol), HFIP 1mL, 2- propenyl benzene (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as white solid, yield 90%.1H NMR (400 MHz, CDCl3) δ7.50-7.43 (m, 2H), 7.33 (t, J = 7.6 Hz, 2H), 7.22 (m, 1H), 6.77 (d, J = 8.5 Hz, 1H), 6.74-6.65 (m, 2H), 3.93 (q, J = 7.0 Hz, 2H), 3.36 (s, J = 15.5 Hz, 2H), 1.75 (s, 3H), 1.36 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 153.4, 153.0, 146.9, 128.3, 127.4, 127.0, 124.5, 113.9, 112.1, 109.4, 89.1, 64.3, 45.2, 29.2, 15.0. HRMS (ESI+): m/z [M+Na]+ calcd for C17H18NaO2 + 277.1199, found 277.1199。
It is similar to Example 2, the difference is that solvent HFIP is replaced using MeCN, yield 14%.
It is similar to Example 2, the difference is that solvent HFIP is replaced using TFE, yield 30%.
Embodiment 3
It is sequentially added in dry reaction flask p methoxy phenol (0.15mmol), HFIP 1mL, 1,2- dihydronaphthalene (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as yellow oily liquid, yield 68%.1H NMR (400 MHz, CDCl3) δ 7.64-7.58 (m, 1H), 7.40- 7.29 (m, 2H), 7.27-7.19 (m, 1H), 6.94-6.88 (m, 1H), 6.80-6.71 (m, 2H), 5.75- 5.68 (m, 1H), 3.85 (s, 3H), 3.76-3.67 (m, 1H), 2.86-2.66 (m, 2H), 2.18-2.07 (m, 1H), 1.94-1.82 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 154.29, 153.50, 138.84, 133.58, 132.53, 130.22, 128.53, 128.32, 126.75, 112.99, 110.84, 109.51, 82.05, 56.08, 41.68, 27.94, 27.71. HRMS (ESI+): m/z [M+Na]+ calcd for C17H16NaO2 +275.1043, found 275.1044。
It is similar to Example 3, the difference is that solvent HFIP is replaced using MeCN, yield 10%.
It is similar to Example 3, the difference is that solvent HFIP is replaced using TFE, yield 25%.
Embodiment 4
P methoxy phenol (0.15mmol), HFIP 1mL, pfluorostyrene are sequentially added in dry reaction flask (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as colourless liquid, yield 50%.1H NMR (400 MHz, CDCl3)δ 7.41-7.34 (m, 2H), 7.09-7.01 (m, 2H), 6.77 (d, J = 8.5 Hz, 2H), 6.71 (dd, J = 8.6, 2.6 Hz, 1H), 5.71 (t, J = 8.7 Hz, 1H), 3.77 (s, 3H), 3.59 (dd, J = 15.7, 9.3 Hz, 1H), 3.16 (dd, J = 15.7, 8.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 161.2, 154.3, 153.5, 137.8, 127.6, 127.5, 127.3, 115.6, 115.4, 113.0, 111.2, 109.2, 83.6, 56.0, 38.9.
HRMS (ESI+): m/z [M+Na]+calcd for C15H13NaO2 +267.0792 and 268.0825, found 267.0788 and 268.0811。
Embodiment 5
It is sequentially added in dry reaction flask p methoxy phenol (0.15mmol), HFIP 1mL, to tert-butyl benzene second Alkene (0.3mmol), stirs and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction is steamed with rotation after reaction It sends out instrument and removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo Furans is faint yellow solid, yield 89%.1H NMR (400 MHz, CDCl3) δ 7.39 (d, J = 8.3 Hz, 2H), 7.34 (d, J = 8.3 Hz, 2H), 6.83 – 6.72 (m, 2H), 6.69 (dd, J = 8.6, 2.2 Hz, 1H), 5.71 (t, J = 8.7 Hz, 1H), 3.76 (s, 3H), 3.57 (dd, J = 15.7, 9.3 Hz, 1H), 3.22 (dd, J = 15.7, 8.2 Hz, 1H), 1.31 (s, 9H). 13C NMR (100 MHz, CDCl3) δ 154.2, 153.8, 151.0, 138.8, 127.7, 125.7, 125.5, 112.9, 111.2, 109.2, 84.2, 56.0, 38.6, 34.6, 31.3. HRMS (ESI+): m/z[M+Na]+ calcd for C19H22NaO2 + 305.1512, found 305.1512。
Embodiment 6
Acamol (0.15mmol), HFIP 1mL, styrene are sequentially added in dry reaction flask (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as white solid, yield 35%.1H NMR (400 MHz, CDCl3) δ 7.47 (s, 2H), 7.37 (dd, J = 7.2, 5.0 Hz, 4H), 7.32 (ddd, J = 6.3, 2.9, 1.3 Hz, 1H), 7.05 (dd, J = 8.4, 2.0 Hz, 1H), 6.77 (d, J = 8.5 Hz, 1H), 5.78 – 5.69 (m, 1H), 3.59 (dd, J = 15.8, 9.4 Hz, 1H), 3.18 (dd, J = 15.8, 8.2 Hz, 1H), 2.13 (s, 3H).13C NMR (100 MHz, CDCl3) δ 168.8, 156.6, 141.7, 131.0, 128.6, 128.1, 127.2, 125.7, 121.0, 118.5, 109.0, 84.5, 38.4, 24.1. HRMS (ESI+): m/z [M+Na]+ calcd for C16H15NNaO2 + 276.0995, found 276.0996。
Embodiment 7
It is sequentially added in dry reaction flask to thanatol (0.15mmol), HFIP 1mL, 1,1- talan (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as weak yellow liquid, yield 50%.1H NMR (400 MHz, CDCl3) δ 7.58-7.43 (m, 4H), 7.30 (t, J = 7.7 Hz, 4H), 7.27-7.19 (m, 2H), 6.83 (d, J = 8.6 Hz, 1H), 6.73 (d, J = 1.2 Hz, 1H), 6.71-6.65 (m, 1H), 3.92 (q, J = 7.0 Hz, 2H), 3.87 (s, 2H), 1.35 (t,J = 7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 153.7, 152.8, 145.4, 128.3, 127.3, 127.2, 126.0, 113.9, 111.8, 109.5, 92.5, 64.3, 44.7, 15.0. HRMS (ESI+): m/z[M +Na]+ calcd for C22H20NaO2 + 339.1356, found 339.1354。
Embodiment 8
6- cyano-beta naphthal (0.15mmol), HFIP 1mL, styrene are sequentially added in dry reaction flask (0.3mmol) is stirred and is slowly added to DDQ(0.18mmol).Thin-layer chromatography monitoring reaction, after reaction, uses rotary evaporation Instrument removes solvent, and using ethyl acetate/petroleum ether=1:50 as eluant, eluent, column chromatographic isolation and purification obtains corresponding dihydrobenzo furan It mutters as colourless liquid, yield 37%.1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 7.79 (d, J = 8.9 Hz, 1H), 7.65-7.55 (m, 2H), 7.43 (t, J = 5.9 Hz, 3H), 7.40 (s, 1H), 7.36 (dd,J = 8.6, 4.7 Hz, 1H), 7.30 (d, J = 8.8 Hz, 1H), 6.02 (dd, J = 9.9, 8.1 Hz, 1H), 3.95 (dd, J = 15.6, 10.1 Hz, 1H), 3.50 (dd, J = 15.6, 7.9 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ 159.8, 141.4, 134.9, 132.2, 130.3, 128.8, 128.4, 128.1, 127.3, 125.7, 123.9, 119.7, 118.8, 113.8, 106.0, 85.4, 36.8. HRMS (ESI+): m/z[M+ Na]+ calcd for C19H13NNaO + 294.0889, found 294.0878。

Claims (3)

1. a kind of synthetic method of Dihydrobenzofuranes class compound, it is characterised in that include the following steps:
Oxidation [3+2] cycloaddition reaction occurs in the presence of DDQ and obtains accordingly for phenol derivatives (a) and styrene derivative (b) Dihydrobenzofuranes class compound (c), reaction dissolvent is hexafluoroisopropanol, reaction be added without catalyst,
R in formula1For C1-C4Alkoxy or acetamido；R2Selected from hydrogen, C1-C4Alkyl or halogen；R3, R4Selected from hydrogen, C1-C4 Alkyl or aryl.
2. the synthetic method of Dihydrobenzofuranes class compound according to claim 1, it is characterised in that: phenol derivative The ratio between molal quantity of object, styrene derivative and DDQ is 1:1.5~2.5:1.0~1.5.
3. the synthetic method of Dihydrobenzofuranes class compound according to claim 1, it is characterised in that: cycloaddition reaction Corresponding Dihydrobenzofuranes class compound is obtained with silica gel column purification afterwards.
CN201611225596.0A 2016-12-27 2016-12-27 A kind of synthetic method of Dihydrobenzofuranes class compound Expired - Fee Related CN106632179B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201611225596.0A CN106632179B (en) 2016-12-27 2016-12-27 A kind of synthetic method of Dihydrobenzofuranes class compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201611225596.0A CN106632179B (en) 2016-12-27 2016-12-27 A kind of synthetic method of Dihydrobenzofuranes class compound

Publications (2)

Publication Number Publication Date
CN106632179A CN106632179A (en) 2017-05-10
CN106632179B true CN106632179B (en) 2019-08-23

Family

ID=58832639

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201611225596.0A Expired - Fee Related CN106632179B (en) 2016-12-27 2016-12-27 A kind of synthetic method of Dihydrobenzofuranes class compound

Country Status (1)

Country Link
CN (1) CN106632179B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107021944B (en) * 2017-05-17 2019-06-21 西北大学 A kind of heterogeneous synthetic method of Dihydrobenzofuranes class compound

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104672247A (en) * 2013-11-28 2015-06-03 中国科学院大连化学物理研究所 Method for synthesizing 2,3-disubstituted-benzodihydrofuran

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104672247A (en) * 2013-11-28 2015-06-03 中国科学院大连化学物理研究所 Method for synthesizing 2,3-disubstituted-benzodihydrofuran

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial;Luke Alvey等;《Bioorganic & Medicinal Chemistry》;20080803;第16卷;第8265页图3，第8266页图4
Concise total synthesis of (±)-serotobenine;Kangjiang Liang等;《Organic & Biomolecular Chemistry》;20160420;第14卷(第20期);第4691页表1，第4692页左栏第3段、右栏第1段
Iron-Catalyzed Oxidative Radical Cross-Coupling/Cyclizaiton between Phenols and Olefins;Zhiliang Huang等;《Angew. Chem. Int. Ed.》;20130603;第52卷;第7151页图2，第7152页表1
Iron-Catalyzed Oxidative Radical Cross-Coupling/Cyclizaiton between Phenols and Olefins;Zhiliang Huang等;《Angew. Chem. Int. Ed.》;20130603;第52卷;第7151页图2，第7152页表1，第7154页右栏第1段
苯酚与烯烃的氧化环加成反应研究进展;崔娜等;《有机化学》;20160908;第37卷;第20-30页

Also Published As

Publication number Publication date
CN106632179A (en) 2017-05-10

Similar Documents

Publication Publication Date Title
Rajasekhar et al. Green Synthesis and Bioactivity of 2-Amino-4H-chromen-4-yl-phosphonates
Righi et al. Convergent synthesis of mosloflavone, negletein and baicalein from crysin
CN105175328B (en) It is a kind of using aromatic amine, aromatic aldehyde, ketone synthesis of quinoline derivatives method
CN107162968B (en) A kind of method of visible light catalytic Tetrahydroquinolinesas oxidative dehydrogenation synthesis of quinoline class compound
Cremonesi et al. One-electron oxidation of 6-substituted benzo [a] pyrenes by manganic acetate. A model for metabolic activation
Bellina et al. Mucochloric Acid: A Useful Synthon for the Selective Synthesis of 4‐Aryl‐3‐chloro‐2 (5H)‐furanones,(Z)‐4‐Aryl‐5‐[1‐(aryl) methylidene]‐3‐chloro‐2 (5H)‐furanones and 3, 4‐Diaryl‐2 (5H)‐furanones
CN108164475B (en) Method for catalytic synthesis of difluoromethyl-substituted linear aryl hetero-ketone
CN106632179B (en) A kind of synthetic method of Dihydrobenzofuranes class compound
Wang et al. Construction of Esters through Sulfuryl Fluoride (SO2F2) Mediated Dehydrative Coupling of Carboxylic Acids with Alcohols at Room Temperature
Wood et al. Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2+ 2+ 2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi
Valderrama et al. Studies on quinones. Part 38: Synthesis and leishmanicidal activity of sesquiterpene 1, 4-quinones
Bora et al. Novel CuCl2-cryptand-[2.2. Benzo] complex: A base free and oxidant free catalyst for Ipso-Hydroxylation of aryl/heteroaryl-boronic acids in water at room temperature
Schubert et al. MoV Reagents in Organic Synthesis
Anzeveno Rotenoid interconversion. Synthesis of deguelin from rotenone
Kidwai et al. First time reported enzymatic synthesis of new series of quinoxalines—A green approach
Kirkham et al. An alkynylboronate cycloaddition strategy to functionalised benzyne derivatives
Xu et al. Selective aerobic oxidation of sulfides to sulfoxides catalyzed by coenzyme NAD+ models
Dash et al. A concise and efficient total synthesis of militarinone D
Zheng et al. Studies on the total synthesis of hirtellanine A: Regioselective synthesis of benzopyran
Konstantinova et al. Synthesis of the C1–C12 Fragment of Calyculin C
Bang et al. 5-Arylidene-2 (5H)-furanone derivatives: synthesis and structure-activity relationship for cytotoxicity
Gusarova et al. Oxidative transition-metal-free cross-coupling of secondary phosphine chalcogenides and alcohols or phenols: a facile, expedient synthesis of phosphinochalcogenoic O-esters
Woydziak et al. Efficient and scalable synthesis of 4-carboxy-pennsylvania green methyl ester: a hydrophobic building block for fluorescent molecular probes
Mao et al. Total synthesis of panaxydol and its stereoisomers as potential anticancer agents
CN107021944B (en) A kind of heterogeneous synthetic method of Dihydrobenzofuranes class compound

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
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20190823

Termination date: 20211227

CF01 Termination of patent right due to non-payment of annual fee