CN107805824B - A kind of synthetic method of biaryl six-membered cyclic lactone class compound - Google Patents

A kind of synthetic method of biaryl six-membered cyclic lactone class compound Download PDF

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CN107805824B
CN107805824B CN201710981981.6A CN201710981981A CN107805824B CN 107805824 B CN107805824 B CN 107805824B CN 201710981981 A CN201710981981 A CN 201710981981A CN 107805824 B CN107805824 B CN 107805824B
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synthetic method
biaryl
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CN107805824A (en
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戴建军
周洁
陶香长
许华建
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Hefei University of Technology
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Abstract

It is that C-O cyclisation is realized by constant-current electrolysis in the presence of supporting electrolyte, obtains biaryl six-membered cyclic lactone class compound after separating-purifying using 2- aryl benzoic acid as raw material the invention discloses a kind of synthetic method of biaryl six-membered cyclic lactone class compound.Applied Electrochemistry method synthesis of the present invention has the characteristics that Atom economy height, green high-efficient, avoids being suitable for industrialized production using metallic catalyst and oxidant, simple process.

Description

A kind of synthetic method of biaryl six-membered cyclic lactone class compound
Technical field
The present invention relates to a kind of synthetic methods of biaryl six-membered cyclic lactone class compound, belong to organic compound synthesis neck Domain.
Background technique
Biaryl six-membered cyclic lactone is widely present in important natural products and drug molecule[1].In recent years, pass through virtue The method preparation biaryl six-membered cyclic lactone of fragrant c h bond activation C-O cyclization is furtherd investigate and obtains important progress[2]。 However, needing the reaction using expensive transition-metal catalyst, excessive oxidant and harshness in existing technology path Condition etc., these defects limit the practicability of these synthetic methods.
[bibliography]
[1](a)B.I.Alo,A.Kandil,P.A.Patil,M.J.Sharp,M.A.Siddiqui and V.Snieckus,J.Org.Chem.,1991,56,3763；(b)H.Abe,K.Nishioka,S.Takeda,M.Arai, Y.Takeuchi and T.Harayama,Tetrahedron Lett.,2005,46,3197；(c)K.Koch,J.Podlech, E.Pfeiffer and M.Metzler,J.Org.Chem.,2005,70,3275；(d)N.Tibrewal,P.Pahari, G.Wang,M.K.Kharel,C.Morris,T.Downey,Y.Hou,T.S.Bugni and J.Rohr, J.Am.Chem.Soc.,2012,134,18181；(e)P.Bhattacharya,S.M.Mandal and A.Basak, Eur.J.Org.Chem.,2016,1439；(f)W.Lin,J.Huang,X.Liao,Z.Yuan,S.Feng,Y.Xie and W.Ma,Pharmacol.Res.,2016,111,849.
[2](a)J.Gallardo-Donaire and R.Martin,J.Am.Chem.Soc.,2013,135,9350； (b)Y.Wang,A.V.Gulevich and V.Gevorgyan,Chem.Eur.J.,2013,19,15836；(b)J.-J.Dai, W.-T.Xu,Y.-D.Wu,W.-M.Zhang,Y.Gong,X.-P.He,X.-Q.Zhang and H.-J.Xu J.Org.Chem., 2015,80,911；(c)X.Wang,J.Gallardo-Donaire and R.Martin,Angew.Chem.,Int.Ed., 2014,53,11084；(d)N.P.Ramirez,I.Bosque and J.C.Gonzalez-Gomez,Org.Lett.,2015, 17,4550.
Summary of the invention
The present invention is directed to the shortcomings that existing synthetic route, provides a kind of synthesis of biaryl six-membered cyclic lactone class compound Method has many advantages, such as simple process and easy to operate.
The synthetic method of biaryl six-membered cyclic lactone class compound of the present invention is passed through using 2- aryl benzoic acid as raw material C-O cyclisation is realized in constant-current electrolysis, obtains biaryl six-membered cyclic lactone class compound after separating-purifying.
Specifically 2- aryl benzoic acid is dissolved in solvent under room temperature, air conditions, in the presence of supporting electrolyte Constant-current electrolysis is carried out, separating-purifying obtains target compound after reaction.
The structural formula of the 2- aryl benzoic acid are as follows:
Wherein: the R1For H, F, NO2、CH3Or OCH3；R2For H, F, Cl, Br, CN, COOH, CF3、OCF3、NO2Or CH3Base Group.
The reaction temperature of synthetic method of the present invention is 25 DEG C, reaction time 5-24h.
The solvent is acetonitrile, water, acetone, chloroform, methanol or tetrahydrofuran.
In constant-current electrolysis electrode used therein, cathode is platinum plate electrode, and anode is graphite electrode or glassy carbon electrode.
Electric current when constant-current electrolysis is 3-12mA.
The supporting electrolyte is lithium perchlorate, sodium carbonate, tetra-n-butyl ammonium hexafluorophosphate, tetra-n-butyl tetrafluoro boric acid At least one of ammonium, sodium tetrafluoroborate, tetraethyl paratoluenesulfonic acid ammonium salt, the concentration of supporting electrolyte are 0.1M.
The separating-purifying is to rotate reaction solution to remove solvent, and by column chromatography, (eluent is petroleum ether and acetic acid second Ester 10:1~50:1 mixing by volume is constituted) purifying, target product can be obtained.
Reaction process of the present invention is as follows:
The C.C.E. refers to constant current electrolysis mode.
The beneficial effects of the present invention are embodied in:
1, synthetic method mild condition of the invention, carries out at room temperature, at a normal；It is easy to operate and safe, environmentally protective；Instead Process is answered not need inert gas shielding；
2, synthetic method substrate applicability of the invention is wide, can be compatible with a variety of functional groups, prepare the aryl of a variety of substituent groups Lactone compound.
Detailed description of the invention
Fig. 1 is reaction process schematic diagram of the present invention.
Specific embodiment
For the feature and advantage that the present invention is further explained, below with reference to specific embodiment to technical solution of the present invention It is described.But the following example limits the present invention only for further illustrating the present invention.
Embodiment 1:
2- Phenylbenzoic acid (0.5mmol), lithium perchlorate are added into the reaction tube of the 25mL equipped with magnetic stir bar (1.0mmol) adds 10.0mL acetonitrile；Reaction tube is fixed on magnetic stirring apparatus, electrode (platinized platinum cathode, graphite is added Anode) lead to 6mA constant-current electrolysis, while uniform stirring reaction solution；Mixture at room temperature after (25 DEG C) reaction 5h, tie by reaction Beam；Solvent is removed with Rotary Evaporators, crude product is obtained through column chromatography (petroleum ether: ethyl acetate=20:1, v/v) separating-purifying Target product (2a), yield 85%.The nuclear magnetic data of the compound are as follows:1H NMR(400MHz,CDCl3) δ 8.38 (dd, J= 7.9,0.9Hz, 1H), 8.09 (d, J=8.1Hz, 1H), 8.03 (dd, J=7.9,1.3Hz, 1H), 7.89-7.73 (m, 1H), 7.67-7.53 (m, 1H), 7.47 (ddd, J=8.4,7.3,1.5Hz, 1H), 7.33 (ddd, J=11.3,6.5,2.3Hz, 2H) .13C NMR(101MHz,CDCl3)δ161.16,151.21,134.82,134.69,130.50,130.41,128.85, 124.53,122.73,121.65,121.17,117.97,117.71.
Embodiment 2:
2- Phenylbenzoic acid (1a) is replaced with 4'- methyl-[1,1'- xenyl] -2- carboxylic acid (1b), other are the same as embodiment 1. Column chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2b), yield 88%.The nuclear magnetic data of the compound Are as follows:1H NMR(400MHz,CDCl3) δ 8.37 (dd, J=8.0,1.0Hz, 1H), 8.07 (d, J=8.1Hz, 1H), 7.92 (d, J =7.9Hz, 1H), 7.86-7.73 (m, 1H), 7.64-7.43 (m, 1H), 7.14 (d, J=8.7Hz, 2H)13C NMR (101MHz,CDCl3)δ161.44,151.24,141.28,134.97,134.77,130.51,128.35,125.66, 122.49,121.42,120.84,117.86,115.40,21.44.
Embodiment 3:
2- Phenylbenzoic acid (1a) is replaced with fluoro- [1,1'- the xenyl] -2- carboxylic acid (1c) of 4'-, other are the same as embodiment 1.Column Chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2c), yield 93%.The nuclear magnetic data of the compound Are as follows:1H NMR(400MHz,CDCl3) δ 8.34 (dd, J=8.0,1.0Hz, 1H), 8.00 (dd, J=8.3,5.6Hz, 2H), 7.86–7.74(m,1H),7.61–7.48(m,1H),7.12–6.97(m,2H).13C NMR(101MHz,CDCl3)δ163.41 (d, J=251.3Hz), 160.75,152.08 (d, J=12.3Hz), 135.07,134.16,130.61,128.74,124.34 (d, J=9.9Hz), 121.48,120.35,114.56 (d, J=3.2Hz), 112.42 (d, J=22.4Hz), 105.03 (d, J =25.3Hz)19F NMR(376MHz,CDCl3)δ-108.36(s).
Embodiment 4:
2- Phenylbenzoic acid (1a) is replaced with chloro- [1,1'- the xenyl] -2- carboxylic acid (1d) of 4'-, other are the same as embodiment 1.Column Chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2d), yield 72%.The nuclear magnetic data of the compound Are as follows:1HNMR(400MHz,CDCl3) δ 8.32 (dd, J=7.9,1.0Hz, 1H), 8.01 (d, J=8.0Hz, 1H), 7.91 (d, J= 8.3Hz,1H),7.87–7.72(m,1H),7.64–7.46(m,1H),7.32–7.24(m,2H).13C NMR(101MHz, CDCl3)δ160.46,151.35,135.84,135.04,133.83,130.60,129.13,124.97,123.73,121.60, 120.74,117.80,116.58.
Embodiment 5:
2- Phenylbenzoic acid (1a) is replaced with bromo- [1,1'- the xenyl] -2- carboxylic acid (1e) of 4'-, other are the same as embodiment 1.Column Chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2e), yield 65%.The nuclear magnetic data of the compound Are as follows:1HNMR(400MHz,CDCl3) δ 8.35 (dd, J=7.9,0.7Hz, 1H), 8.04 (d, J=8.1Hz, 1H), 7.88 (d, J= 8.5Hz, 1H), 7.85-7.78 (m, 1H), 7.63-7.56 (m, 1H), 7.48 (d, J=1.9Hz, 1H), 7.44 (dd, J=8.5, 1.9Hz,1H).13C NMR(101MHz,CDCl3)δ160.43,151.39,135.07,133.92,130.67,129.25, 127.81,123.91,123.67,121.61,120.90,120.81,117.04.
Embodiment 6:
2- Phenylbenzoic acid (1a) is replaced with 4'- trifluoromethyl-[1,1'- xenyl] -2- carboxylic acid (1f), other are the same as implementation Example 1.Column chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2f), yield 87%.The nuclear-magnetism of the compound Data are as follows:1H NMR(400MHz,CDCl3) δ 8.42 (dd, J=7.9,1.0Hz, 1H), 8.17 (t, J=7.8Hz, 2H), 7.89 (td, J=7.8,1.4Hz, 1H), 7.74-7.63 (m, 1H), 7.63-7.53 (m, 2H)13C NMR(101MHz,CDCl3)δ (160.25,150.94,135.23,133.34,132.22 q, J=33.5Hz), 130.83,130.15,123.64,123.29 (q, J=272.5Hz), 122.20,121.62,121.10 (q, J=3.6Hz), 121.08,115.21 (q, J=4.0Hz)19F NMR(376MHz,CDCl3)δ-62.79.
Embodiment 7:
2- Phenylbenzoic acid (1a) is replaced with 4'- nitro-[1,1'- xenyl] -2- carboxylic acid (1g), other are the same as embodiment 1. Column chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2g), yield 60%.The nuclear magnetic data of the compound Are as follows:1H NMR(600MHz,CDCl3) δ 8.61 (d, J=8.7Hz, 1H), 8.52 (d, J=8.0Hz, 1H), 8.28 (d, J= 7.9Hz, 1H), 8.22-8.14 (m, 2H), 8.02 (t, J=7.6Hz, 1H), 7.81 (t, J=7.6Hz, 1H)；13C NMR (151MHz,CDCl3)δ167.32,158.34,155.70,143.49,140.33,139.02,137.75,132.98, 131.72,131.66,129.23,126.91,120.54.
Embodiment 8:
2- Phenylbenzoic acid (1a) is replaced with 4'- itrile group-[1,1'- xenyl] -2- carboxylic acid (1h), other are the same as embodiment 1. Column chromatography (petroleum ether: ethyl acetate=10:1, v/v) obtains target product (2h), yield 57%.The nuclear magnetic data of the compound Are as follows:1H NMR(400MHz,CDCl3) δ 8.45 (d, J=7.8Hz, 1H), 8.18 (t, J=7.2Hz, 2H), 7.92 (t, J= 7.6Hz, 1H), 7.72 (t, J=7.6Hz, 1H), 7.66 (s, 1H), 7.62 (d, J=8.2Hz, 1H)；13C NMR(101MHz, CDCl3)δ159.80,150.92,135.39,132.94,131.00,130.74,127.73,123.91,122.45,122.31, 121.79,121.66,117.59,113.53.
Embodiment 9:
2- Phenylbenzoic acid (1a) is replaced with 6- methyl-[1,1'- xenyl] -2- carboxylic acid (1i), other are the same as embodiment 1. Column chromatography (petroleum ether: ethyl acetate=20:1, v/v) obtains target product (2i), yield 64%.The nuclear magnetic data of the compound Are as follows:1H NMR(400MHz,CDCl3) δ 8.32 (d, J=7.7Hz, 1H), 8.25 (d, J=8.2Hz, 1H), 7.61 (d, J= 7.4Hz, 1H), 7.44 (ddd, J=7.6,5.7,2.8Hz, 2H), 7.39-7.33 (m, 1H), 7.33-7.27 (m, 1H), 2.85 (s,3H).13CNMR(101MHz,CDCl3)δ161.63,151.08,139.03,135.00,133.40,129.56,129.04, 128.17,127.09,123.97,122.61,
Embodiment 10:
2- Phenylbenzoic acid (1a) is replaced with fluoro- [1,1'- the xenyl] -2- carboxylic acid (1j) of 4,5- bis-, other same embodiments 1.Column chromatography (petroleum ether: ethyl acetate=50:1, v/v) obtains target product (2j), yield 85%.The nuclear-magnetism number of the compound According to are as follows:1H NMR(400MHz,CDCl3) δ 8.18 (dd, J=9.9,8.0Hz, 1H), 7.97-7.80 (m, 2H), 7.53 (td, J= 7.6,1.4Hz, 1H), 7.37 (ddd, J=6.1,3.6,1.2Hz, 2H)13C NMR(101MHz,CDCl3) δ 159.40 (d, J= 1.8Hz), 155.36 (dd, J=259.7,13.8Hz), 151.26,150.64 (dd, J=254.2,13.7Hz), 133.14 (dd, J=8.2,3.4Hz), 131.19,124.98,122.84,119.18 (dd, J=18.9,2.4Hz), 118.37 (dd, J= ), 6.2,2.9Hz 117.99,116.68 (dd, J=2.2,1.7Hz), 110.73 (d, J=19.4Hz)19F NMR(376MHz, CDCl3) δ -124.86 (d, J=21.5Hz), -133.84 (d, J=21.4Hz)
Embodiment 11:
2- Phenylbenzoic acid (1a) is replaced with 3- tolylthiophene -2- carboxylic acid (1k), other are the same as embodiment 1.Column chromatographs (petroleum Ether: ethyl acetate=20:1, v/v) obtain target product (2k), yield 88%.The nuclear magnetic data of the compound are as follows:1H NMR (400MHz,CDCl3) δ 7.90 (d, J=5.2Hz, 1H), 7.76 (dd, J=7.8,1.4Hz, 1H), 7.59 (d, J=5.2Hz, 1H), 7.45 (ddd, J=8.7,7.2,1.6Hz, 1H), 7.36 (dd, J=8.3,0.9Hz, 1H), 7.30 (td, J=7.8, 1.2Hz,1H).13C NMR(101MHz,CDCl3)δ157.14,152.46,144.95,136.89,130.11,124.58, 124.25,123.79,122.37,117.36,117.25.
The method of electrochemistry formated biaryl lactone compound provided by the invention is described in detail above.With Upper described only the embodiment of the present invention, is not intended to limit the scope of the invention.Before not departing from the principle of the invention It puts, the present invention can be made improvements and modifications, these improvement and modification are also included within the scope of patent protection of the present invention.

Claims (9)

1. a kind of synthetic method of biaryl six-membered cyclic lactone class compound, it is characterised in that: be with 2- aryl benzoic acid for original Material realizes C-O cyclisation by constant-current electrolysis, obtains biaryl six-membered cyclic lactone class compound after separating-purifying；
The structural formula of the 2- aryl benzoic acid are as follows:
Wherein: the R1For H, F, NO2、CH3Or OCH3；R2For H, F, Cl, Br, CN, COOH, CF3、OCF3、NO2Or CH3Group.
2. synthetic method according to claim 1, it is characterised in that: by 2- aryl benzoic acid under room temperature, air conditions It is dissolved in solvent, constant-current electrolysis is carried out in the presence of supporting electrolyte, separating-purifying obtains target chemical combination after reaction Object.
3. synthetic method according to claim 2, it is characterised in that:
Reaction temperature is 25 DEG C, reaction time 5-24h.
4. synthetic method according to claim 2, it is characterised in that:
The solvent is acetonitrile, acetone, chloroform, methanol or tetrahydrofuran.
5. synthetic method according to claim 2, it is characterised in that:
In constant-current electrolysis electrode used therein, cathode is platinum plate electrode, and anode is graphite electrode or glassy carbon electrode.
6. synthetic method according to claim 2, it is characterised in that:
Electric current when constant-current electrolysis is 3-12mA.
7. synthetic method according to claim 2, it is characterised in that:
The supporting electrolyte is lithium perchlorate, sodium carbonate, tetra-n-butyl ammonium hexafluorophosphate, tetra-n-butyl ammonium tetrafluoroborate, four At least one of sodium fluoborate, tetraethyl paratoluenesulfonic acid ammonium salt, the concentration of supporting electrolyte are 0.1M.
8. synthetic method according to claim 2, it is characterised in that:
The separating-purifying is reaction solution to be rotated to removing solvent target product can be obtained by column chromatographic purifying.
9. synthetic method according to claim 8, it is characterised in that:
Eluent when column chromatography for separation is that the 10:1~50:1 mixing by volume of petroleum ether and ethyl acetate is constituted.
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