CN115537853A - Direct electrochemical synthesis method of triarylamine compound - Google Patents

Direct electrochemical synthesis method of triarylamine compound Download PDF

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CN115537853A
CN115537853A CN202211247447.XA CN202211247447A CN115537853A CN 115537853 A CN115537853 A CN 115537853A CN 202211247447 A CN202211247447 A CN 202211247447A CN 115537853 A CN115537853 A CN 115537853A
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phenothiazine
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李美超
冯成龙
沈振陆
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Zhejiang University of Technology ZJUT
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Abstract

The invention relates to a direct electrochemical synthesis method of triarylamine compounds, which takes phenothiazine compounds (II) and 2-arylindolizine compounds (III) as reaction raw materials, adopts a three-electrode system, takes a graphite electrode or a Pt electrode as a cathode and an anode, takes 0.1mol/L silver nitrate acetonitrile solution as a reference electrode, carries out electrolytic reaction in an organic solvent containing supporting electrolyte by stirring at 15-45 ℃ and 0.1-0.3V, and obtains the triarylamine compounds with the structure shown in formula (I) by separation treatment after the reaction is finished. The invention has the following beneficial effects: (1) The invention uses clean electric energy as oxidant, thus reducing environmental cost; (2) the reaction substrate has good universality; and (3) the product yield is high.

Description

Direct electrochemical synthesis method of triarylamine compound
(I) technical field
The invention relates to a direct electrochemical synthesis method of triarylamine compounds.
(II) background of the invention
The triarylamine compound has good hole transmission capability and is widely applied to the fields of organic light-emitting diodes, sensitized solar cells, photochromic materials and the like. The phenothiazine compound is used as a special diarylamine compound, and has the characteristics of mature production technology, low price, wide application and the like. In addition, the 2-aryl indolizine compound has good photoelectric characteristics as the phenothiazine compound, so that the triarylamine compound synthesized by using the 2-aryl indolizine compound and the phenothiazine compound as raw materials has good development prospect in the field of photoelectric materials.
The traditional synthesis method of triarylamine compounds is to use diarylamine and aromatic hydrocarbon as raw materials and prepare the triarylamine compounds by constructing C-N bonds, but the synthesis methods inevitably need to use chemical oxidants, transition metal catalysts or photosensitizers, and can suffer from problems of isomer mixing and the like. Meanwhile, the method also does not accord with the characteristics of sustainable development and green chemistry.
In recent years, electrochemistry is used as an environment-friendly and efficient synthesis method, and a new possibility is provided for green organic synthesis. In the electrochemical reaction process, the redox agent and the catalyst are electrically charged, an external oxidant and the catalyst are not needed, the atom utilization rate is improved, and the separation and purification of the product are facilitated.
Disclosure of the invention
The invention aims to provide a direct electrochemical synthesis method of triarylamine compounds.
The technical scheme adopted by the invention is as follows:
a method for the direct electrochemical synthesis of triarylamine compounds, the method comprising: taking phenothiazine compounds with a structural formula shown in a formula (II) and 2-aryl indolizine compounds with a structural formula shown in a formula (III) as reaction raw materials, adopting a three-electrode system, taking a graphite electrode or a Pt electrode as a cathode and an anode (the cathode and the anode can be the same or different), taking 0.1mol/L silver nitrate acetonitrile solution as a reference electrode, stirring the solution in an organic solvent containing supporting electrolyte at 15-45 ℃ and 0.1-0.3V for electrolytic reaction, and separating the solution after the reaction is finished to obtain triarylamine compounds with a structural formula shown in a formula (I); the supporting electrolyte is LiClO 4 、 n Bu 4 NBF 4 、 n Bu 4 NPF 6 Or NaClO 4 Preferably LiClO 4 The organic solvent is N, N-dimethylformamide, acetonitrile or ethyl acetate, preferably N, N-dimethylformamide;
Figure BDA0003886579720000021
in the formulae (I) to (III),
R 1 is H, C-C4 alkyl, halogen, C1-C2 alkoxy, nitro, cyano, trifluoromethyl or acetyl;
R 2 is phenyl, substituted phenyl, naphthyl or substituted naphthyl, and the substituents (one or more) of the substituted phenyl and the substituted naphthyl are independently selected from one of the following groups: halogen, nitro, C1-C4 alkyl or C1-C4 alkoxy;
R 3 is H, C-C4 alkyl, C1-C4 alkoxy, chlorine, bromine or fluorine.
Preferably, R 1 Is H, cl, methoxy, methylthio, trifluoromethyl, cyano or acetyl, R 2 Is phenyl, halogenated phenyl, C1-C4 alkyl substituted phenyl, C1-C4 alkoxy substituted phenyl or naphthyl, R 3 Is H, methyl or bromine.
The mass ratio of the phenothiazine compound to the indolizine compound is 100:80 to 150, preferably 100:110 to 130.
The reactions involved in the present invention are as follows:
Figure BDA0003886579720000031
the reaction mechanism is as shown above: the indolizine loses an electron at the anode to form an indolizine cation free radical, the phenothiazine loses an electron and a hydrogen ion at the anode to form a phenothiazine free radical, and the indolizine cation free radical and the phenothiazine free radical are coupled and then lose a hydrogen ion to obtain a product. The chemical synthesis reaction can also be synthesized by adopting a constant current method, but the product yield is low mainly because the raw materials can be polymerized on the surface of an electrode under the condition of constant current.
The three-electrode system is designed to eliminate the large error of electrode potential caused by polarization current, and introduces a reference electrode for stabilizing a working electrode on the basis of the conventional two-electrode system (working electrode and counter electrode).
The supporting electrolyte is an electrolyte that increases the conductivity of the solution in the chemical cell and does not itself participate in the electrochemical reaction. Preferably, the concentration of the supporting electrolyte in the organic solvent is 0.05 to 0.15mol/L.
The recommended mass consumption of the organic solvent is 150-400 times of that of the reaction substrate phenothiazine compound.
Specifically, the separation treatment method comprises the following steps: after the reaction is finished, the solvent is evaporated under reduced pressure, and then thin layer chromatography separation is carried out, wherein the volume ratio of petroleum ether/ethyl acetate is 20:1 as developing agent, collecting thin layer containing target compound, eluting with dichloromethane, filtering, and evaporating the filtrate to remove solvent to obtain the triarylamine compound.
Preferably, the method is as follows: taking phenothiazine compounds with a structural formula shown in a formula (II) and 2-aryl indolizine compounds with a structural formula shown in a formula (III) as raw materials, adopting a three-electrode system, wherein a cathode and an anode are both Pt electrodes, taking 0.1mol/L silver nitrate acetonitrile solution as a reference electrode, and adding 0.05-0.15 mol/L LiClO 4 Stirring and electrolyzing the N, N-dimethylformamide solution for 3.5 to 7.0 hours at the temperature of between 15 and 45 ℃ and at the pressure of between 0.1 and 0.3V, evaporating the solvent under reduced pressure, and then carrying out thin-layer chromatography separation, wherein the volume ratio of petroleum ether to ethyl acetate is 20:1 as developing agent, collecting thin layer containing target compound, eluting with dichloromethane, filtering, and evaporating the filtrate to remove solvent to obtain the triarylamine compound.
The invention has the following beneficial effects: (1) The invention uses clean electric energy as oxidant, thus reducing environmental cost; (2) the reaction substrate has good universality; and (3) the product yield is high.
(IV) description of the drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1));
FIG. 2 is a nuclear magnetic carbon spectrum of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1)).
(V) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
the structural formulas of the triarylamine compounds prepared in the examples are respectively shown in formulas (I-1) to (I-26):
Figure BDA0003886579720000051
Figure BDA0003886579720000061
example 1: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
A three-electrode system is adopted in the reaction, the cathode and the anode are both Pt electrodes, and 0.1mol/L silver nitrate acetonitrile solution is used as a reference electrode. 0.1mol/L LiClO was added to a 30ml beaker 4 A solution of N, N-dimethylformamide (15 mL), phenothiazine (0.20 mmol), and 2-phenylindolizine (0.24 mmol). Constant potential electrolysis is carried out at 25 ℃ and 0.2V, and the reaction is finished after 3.5 h. And (3) evaporating the solvent under reduced pressure, and then carrying out thin-layer chromatography separation, wherein the volume ratio of petroleum ether/ethyl acetate is 20:1 as developing agent, collecting thin layer containing target compound, eluting with dichloromethane, filtering, evaporating filtrate to remove solvent to obtain product 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (nuclear magnetic hydrogen spectrum is shown in figure 1, and nuclear magnetic carbon spectrum is shown in figure 2), with yield of 85%.
1 H NMR(400MHz,CDCl 3 )δ7.87-7.83(m,3H),7.51-7.49(m,1H), 7.38-7.35(m,2H),7.26-7.25(m,1H),7.10-7.08(m,2H),6.95(s,1H), 6.86-6.79(m,5H),6.55-6.51(m,1H),6.13-6.11(m,2H). 13 C NMR(101MHz, CDCl 3 )δ141.6,134.0,131.0,128.9,127.7,127.2,127.1,127.0,125.6,123.6, 121.6,121.2,119.3,118.8,116.5,115.9,111.3,96.9.HRMS(ESI)calculated for C 26 H 19 N 2 S + [M+H] + :391.1263；found:391.1263.
Example 2: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the voltage is changed to 0.1V, the reaction time is 7.0H, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 82%.
Example 3: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the voltage is changed to 0.3V, the reaction time is 2.0H, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 79%.
Example 4: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the temperature is changed to 15 ℃ and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 72%.
Example 5: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The procedure is as in example 1, except that the temperature is changed to 35 ℃ and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 85%.
Example 6: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the amount of 2-phenylindolizine used was changed to 0.20mmol, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 79%.
Example 7: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the amount of 2-phenylindolizine used was changed to 0.30mmol, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 85%.
Example 8: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure is as in example 1, except that the solvent is changed to acetonitrile and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 55%.
Example 9: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure was the same as in example 1, except that the supporting electrolyte was changed to n Bu 4 NBF 4 The yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 63%.
Example 10: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure was the same as in example 1, except that the supporting electrolyte was changed to n Bu 4 NPF 6 The yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 67%.
Example 11: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure was the same as in example 1, except that the supporting electrolyte was changed to NaClO 4 The yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 75%.
Example 12: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure was as in example 1, except that the anode was changed to a graphite electrode, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 80%.
Example 13: preparation of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-1))
The reaction procedure was the same as in example 1, except that the cathode and the anode were each replaced with a graphite electrode, and the yield of 10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 75%.
Example 14: preparation of 2-chloro-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-2))
The reaction procedure was as in example 1, except that the phenothiazine was changed to 2-chlorophenothiazine, and the yield of 2-chloro-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 79%.
1 H NMR(500MHz,CDCl 3 )δ7.82-7.78(m,3H),7.51(d,J＝8.9Hz, 1H),7.39-7.36(m,2H),7.27-7.24(m,1H),7.07(m,1H),6.97(d,J＝8.2Hz, 1H),6.93(s,1H),6.88–6.79(m,4H),6.57-6.55(m,1H),6.08-6.07(m,2H). 13 C NMR(125MHz,CDCl 3 )δ142.9,141.1,133.7,133.5,131.2,129.0,127.9, 127.6,127.3,127.2,127.0,125.7,124.0,123.6,121.3,120.8,119.7,119.5, 119.0,116.1,115.96,115.6,111.6,97.2.HRMS(ESI)m/z calculated for C 26 H 18 ClN 2 S + [M+H] + 425.0874,found 425.0870.
Example 15: preparation of 2-trifluoromethyl-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-3))
The reaction procedure was as in example 1, except that phenothiazine was changed to 2-trifluoromethylphenothiazine, and the yield of 2-trifluoromethyl-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 72%.
1 H NMR(500MHz,CDCl 3 )δ7.83-7.81(m,1H),7.76-7.72(m,2H), 7.51(d,J＝9.0Hz,1H),7.35(t,J＝7.7Hz,2H),7.27-7.22(m,1H),7.12(d,J ＝8.0Hz,1H),7.07-7.06(m,2H),6.93(s,1H),6.90-6.81(m,3H),6.59-6.54 (m,1H),6.27(d,J＝0.8Hz,1H),6.09-6.07(m,1H). 13 C NMR(125MHz, CDCl 3 )δ142.3,141.2,133.8,131.3,130.0(q,J C-F ＝32.8Hz),129.0,128.2, 127.34,127.26,127.2,127.1,126.1,124.2,123.7(q,J C-F ＝273.4Hz),121.3, 120.24,120.23(q,J C-F ＝3.8Hz),119.5,119.0,116.2,115.3,112.4(q,J C-F ＝ 3.8Hz),111.6,97.4. 19 F NMR(377MHz,CDCl 3 )δ-63.13(s).HRMS(ESI) m/z calculated for C 27 H 18 F 3 N 2 S + [M+H] + 459.1137,found 459.1135.
Example 16: preparation of 2-acetyl-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-4))
The reaction procedure was as in example 1, except that phenothiazine was changed to 2-acetylphenothiazine, and the yield of 2-acetyl-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 72%.
1 H NMR(600MHz,CDCl3)δ7.89(d,J＝7.0Hz,1H),7.80(d,J＝7.7 Hz,2H),7.53(d,J＝9.0Hz,1H),7.44-7.42(m,1H),7.37(t,J＝7.7Hz,2H), 7.28-7.25(m,1H),7.15-7.06(m,2H),6.96(s,1H),6.92-6.81(m,3H),6.67(d, J＝1.3Hz,1H),6.57(t,J＝6.7Hz,1H),6.15(d,J＝8.0Hz,1H),2.14(s,3H). 13 C NMR(151MHz,CDCl3)δ196.8,141.6,141.3,136.5,134.0,131.2, 129.0,128.23,128.21,127.3,127.2,127.0,126.8,126.1,124.0,123.4,121.3, 120.3,119.5,118.9,116.2,115.54,115.52,111.5,97.3,26.3.HRMS(ESI)m/z calculated for C 28 H 21 N 2 OS + [M+H] + 433.1369,found 433.1367.
Example 17: preparation of 2-cyano-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-5))
The reaction procedure was as in example 1 except that the phenothiazine was changed to 2-cyanophenothiazine, and the yield of 2-cyano-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 41%.
1 H NMR(600MHz,CDCl 3 )δ7.76-7.72(m,3H),7.52(d,J＝8.9Hz, 1H),7.36-7.34(m,2H),7.26-7.24(m,1H)7.05-7.01(m,3H),6.91(s,1H), 6.88-6.81(m,3H),6.58-6.56(m,1H),6.15(s,1H),6.04(d,J＝7.9Hz, 1H). 13 C NMR(151MHz,CDCl 3 )δ142.4,140.5,133.5,131.5,129.0,128.5, 128.3,127.4,127.3,127.1,127.0,125.7,124.4,121.0,119.7,119.4,119.2, 118.6,118.0,116.2,114.8,111.9,111.0,97.5.HRMS(ESI)m/z calculated for C 27 H 17 N 3 SNa + [M+Na] + 438.1035,found 438.1036.
Example 18: preparation of 2-methylsulfanyl-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-6))
The reaction procedure was as in example 1, except that the phenothiazine was changed to 2-methylthiophenothiazine, and the yield of 2-methylthio-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 86%.
1 H NMR(500MHz,CDCl 3 )δ7.85(d,J＝7.1Hz,1H),7.81-7.77(m, 2H),7.47(d,J＝8.9Hz,1H),7.34(t,J＝7.7Hz,2H),7.25-7.21(m,1H), 7.10-7.08(m,1H),6.97(d,J＝8.5Hz,1H),6.91(s,1H),6.87-6.84(m,1H), 6.82-6.77(m,2H),6.55-6.50(m,1H),6.43-6.41(m,1H),6.13-6.11(m,1H), 5.78(d,J＝2.5Hz,1H),3.43(s,3H). 13 C NMR(125MHz,CDCl 3 )δ159.8, 143.0,141.5,134.0,131.0,129.0,127.6,127.4,127.2,127.1,127.0,125.8, 123.6,121.9,121.6,119.3,118.8,116.3,116.1,112.0,111.3,108.5,103.3, 97.0,55.2.HRMS(ESI)calculated for C 27 H 21 N 2 S 2 + [M+H] + :437.1141；found: 437.1124.
Example 19: preparation of 2-methoxy-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-7))
The reaction procedure was as in example 1, except that the phenothiazine was changed to 2-methoxyphenothiazine, and the yield of 2-methoxy-10- (2-phenylindolizin-3-yl) -10H-phenothiazine was 88%.
1 H NMR(500MHz,CDCl 3 )δ7.89-7.86(m,1H),7.79-7.78(m,2H), 7.48(d,J＝9.0Hz,1H),7.35(t,J＝7.7Hz,2H),7.25-7.22(m,1H),7.10-7.08 (m,1H),6.97(d,J＝8.1Hz,1H),6.92(s,1H),6.89-6.77(m,3H),6.76-6.74 m,1H),6.55-6.52(m,1H),6.16-6.14(m,1H),6.06(d,J＝1.9Hz,1H),2.00 (s,3H). 13 C NMR(125MHz,CDCl 3 )δ142.1,141.6,138.0,134.0,131.0, 129.0,127.7,127.2,127.0,126.0,123.7,122.0,121.6,121.5,119.3,118.8, 118.0,116.2,116.0,114.2,111.37,96.9,15.7.HRMS(ESI)calculated for C 27 H 20 KN 2 S + [M+K] + :459.0928；found:459.0931.
Example 20: preparation of 1-chloro-10- (2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-8))
The procedure is as in example 1, except that the phenothiazine is changed to 1-chlorophenothiazine, and the yield of 1-chloro-10- (2-phenylindolizin-3-yl) -10H-phenothiazine is 55%.
1 H NMR(400MHz,CDCl3)δ7.85(d,J＝7.0Hz,1H),7.83-7.77(m, 2H),7.49(d,J＝9.0Hz,1H),7.37(t,J＝7.7Hz,2H),7.27-7.23(m,1H), 7.09-7.08(m,1H),6.95-6.75(m,5H),6.67(t,J＝8.1Hz,1H),6.57-6.53(m, 1H),6.04-6.01(m,1H),5.94-5.92(m,1H). 13 C NMR(101MHz,CDCl 3 )δ 142.5,140.7,133.7,131.1,130.9,129.0,128.1,127.6,127.3,127.2,127.1, 125.7,123.8,121.4,121.1,119.9,119.4,118.9,115.9,115.8,113.9,111.5, 96.99.HRMS(ESI)m/z calculated for C 26 H 18 ClN 2 S + [M+H] + 425.0874, found 425.0874.
Example 21: preparation of 10- (2- (p-tolyl) indolizin-3-yl) -10H-phenothiazine (formula (I-9))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (p-tolyl) indolizine and the yield of 10- (2- (p-tolyl) indolizin-3-yl) -10H-phenothiazine is 87%.
1 H NMR(500MHz,CDCl 3 )δ7.86(d,J＝7.2Hz,1H),7.73(d,J＝8.2 Hz,2H),7.48(d,J＝9.0Hz,1H),7.17(d,J＝8.1Hz,2H),7.09-7.07(M,2H), 6.92(s,1H),6.86-6.85(M,2H),6.82-6.77(m,3H),6.53-6.50(m,1H), 6.13-6.11(m,2H),2.33(s,3H). 13 C NMR(125MHz,CDCl 3 )δ141.7,136.9, 131.0,129.7,129.3,127.7,127.0,126.9,125.7,123.5,121.6,121.2,119.2, 118.7,116.2,116.0,111.1,96.7,21.3.HRMS(ESI)m/z calculated for C 27 H 21 N 2 S + [M+H] + 405.1420,found 405.1415.
Example 22: preparation of 10- (2- (4-methoxyphenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-10)))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (4-methoxyphenyl) indolizine and the yield of 10- (2- (4-methoxyphenyl) indolizin-3-yl) -10H-phenothiazine is 91%.
1 H NMR(500MHz,CDCl 3 )δ7.85-7.82(m,1H),7.77-7.72(m,2H), 7.46(d,J＝9.0Hz,1H),7.08-7.06(m,2H),6.91-6.88(m,2H),6.86-6.82(m, 3H),6.81-6.77(m,3H),6.52-6.50(m,1H),6.11-6.10(m,2H),3.78(s,3H). 13 C NMR(125MHz,CDCl 3 )δ158.9,141.7,131.0,128.3,127.7,127.0,126.5, 125.5,123.6,121.6,121.2,119.1,118.7,115.94,115.86,114.4,111.0,96.4, 55.3.HRMS(ESI)m/z calculated for C 27 H 21 N 2 OS + [M+H] + 421.1369,found 421.1366.
Example 23: preparation of 10- (2- (4-bromophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-11))
The procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (4-bromophenyl) indolizine and the yield of 10- (2- (4-bromophenyl) indolizin-3-yl) -10H-phenothiazine is 75%.
1 H NMR(500MHz,CDCl 3 )δ7.83-7.81(m,1H),7.69-7.64(m,2H), 7.50-7.44(m,3H),7.08-7.06(m,2H),6.87-6.83(m,3H),6.82-6.78(m,3H), 6.55-6.52(m,1H),6.05-6.03m,2H). 13 C NMR(125MHz,CDCl 3 )δ141.5, 132.9,132.1,131.1,128.7,127.8,127.1,124.4,123.7,121.7,121.2,121.1, 119.4,119.0,116.6,115.7,111.6,96.7.HRMS(ESI)m/z calculated for C 26 H 18 BrN 2 S + [M+H] + 469.0369,found 469.0369.
Example 24: preparation of 10- (2- (4-fluorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-12)))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (4-fluorophenyl) indolizine, the developing solvent is petroleum ether, and the yield of 10- (2- (4-fluorophenyl) indolizin-3-yl) -10H-phenothiazine is 73%.
1 H NMR(400MHz,CDCl 3 )δ7.85-7.78m,3H),7.50(d,J＝9.0Hz,1H), 7.13-7.01(m,4H),6.91-6.77(m,6H),6.56 -6.52m,1H),6.09(d,J＝8.0Hz, 2H). 13 C NMR(101MHz,CDCl 3 )δ162.09(d,J C-F ＝246.4Hz),141.6,131.1, 130.1(d,J C-F ＝3.1Hz),128.8(d,J C-F ＝7.9Hz),127.7,127.1,124.6,123.7, 121.6,121.1,119.3,118.9,116.2,115.9,115.7(d,J C-F ＝3.1Hz),111.4,96.7. 19 F NMR(377MHz,CDCl 3 )δ-115.22(s).HRMS(ESI)m/z calculated for C 26 H 18 FN 2 S + [M+H] + 409.1169,found 409.1169.
Example 25: preparation of 10- (2- (4-chlorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-13))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (4-chlorophenyl) indolizine and the yield of 10- (2- (4-chlorophenyl) indolizin-3-yl) -10H-phenothiazine is 83%.
1 H NMR(500MHz,CDCl 3 )δ7.84-7.82(m,1H),7.77-7.71(m,2H),7.49 (d,J＝9.0Hz,1H),7.34-7.29(m,2H),7.09-7.07(m,2H),6.89-6.78(m,6H), 6.56-6.51(m,1H),6.07-6.05(m,2H). 13 C NMR(125MHz,CDCl 3 )δ141.5, 132.9,132.4,131.1,129.1,128.4,127.7,127.1,124.4,123.7,121.6,121.2, 119.4,119.01,116.5,115.7,111.5,96.7.HRMS(ESI)m/z calculated for C 26 H 18 ClN 2 S + [M+H] + 425.0874,found 425.0870.
Example 26: preparation of 10- (2- (2-fluorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-14))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (2-fluorophenyl) indolizine and the yield of 10- (2- (2-fluorophenyl) indolizin-3-yl) -10H-phenothiazine is 70%.
1 H NMR(400MHz,CDCl 3 )δ7.77(d,J＝7.0Hz,1H),7.74-7.70m,1H), 7.55(d,J＝9.0Hz,1H),7.25-7.04(m,6H),6.88-6.80(m,4H),6.58-6.52(m, 1H),6.04-6.02(m,2H). 13 C NMR(101MHz,CDCl 3 )δ160.3(d,J C-F ＝249.3 Hz),141.7,130.7(d,J C-F ＝1.4Hz),130.0(d,J C-F ＝3.5Hz),128.7(d,J C-F ＝ 8.5Hz),127.7,127.0,124.5(d,J C-F ＝3.5Hz),123.5,121.8(d,J C-F ＝12.4Hz), 121.5,120.7,119.7(d,J C-F ＝8.0Hz),118.6,117.1,116.3,116.0,115.5,111.5, 100.0(d,J C-F ＝9.5Hz). 19 F NMR(377MHz,CDCl 3 )δ-114.43(s).HRMS (ESI)m/z calculated for C 26 H 18 FN 2 S + [M+H] + 409.1169,found 409.1169.
Example 27: preparation of 10- (2- (2-chlorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-15))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (2-chlorophenyl) indolizine and the yield of 10- (2- (2-chlorophenyl) indolizin-3-yl) -10H-phenothiazine is 77%.
1 H NMR(400MHz,DMSO)δ7.57-7.54(m,2H),7.39-7.37(m,1H), 7.20-7.07(m,3H),6.95-6.89(m,2H),6.84-6.70(m,6H),6.59-6.53(m,1H), 5.73-5.66(m,2H). 13 C NMR(101MHz,DMSO)δ141.3,132.6,132.5, 131.05,130.1,130.0,129.2,127.8,127.1,126.9,123.7,122.5,121.5,119.7, 119.0,18.9,116.8,114.6,111.9,100.3.HRMS(ESI)m/z calculated for C 26 H 18 ClN 2 S + [M+H] + 425.0874,found 425.0870.
Example 28: preparation of 10- (2- (3-methoxyphenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-16))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (3-methoxyphenyl) indolizine and the yield of 10- (2- (3-methoxyphenyl) indolizin-3-yl) -10H-phenothiazine is 88%.
1 H NMR(500MHz,CDCl 3 )δ7.82-7.80(m,1H),7.50(d,J＝8.9Hz, 1H),7.43-7.36(m,2H),7.28-7.24(m,1H),7.06-7.05(m,2H),6.92(s,1H), 6.87-6.76(m,6H),6.54-6.51(m,1H),6.06-6.04(m,2H),3.69(s,3H). 13 C NMR(125MHz,CDCl 3 )δ156.0,141.6,135.2,131.0,129.8,127.7,126.9, 125.3,123.6,121.6,120.8,119.7,119.4,118.8,116.4,115.8,113.7,111.9, 111.3,97.1,55.1.HRMS(ESI)m/z calculated for C 27 H 21 N 2 OS + (M+H) + 421.1369,found 421.1365.
Example 29: preparation of 10- (2- (3-chlorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-17))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (3-chlorophenyl) indolizine and the yield of 10- (2- (3-chlorophenyl) indolizin-3-yl) -10H-phenothiazine is 82%.
1 H NMR(500MHz,CDCl 3 )δ7.81-7.80(m,2H),7.67-7.66(m,1H), 7.50(d,J＝9.0Hz,1H),7.25–7.18(m,2H),7.08-7.07(m,2H),6.88(s,1H), 6.87-6.78(m,5H),6.56-6.52(m,1H),6.04-6.02(m,2H). 13 C NMR(125MHz, CDCl 3 )δ141.6,135.8,134.7,131.1,130.2,127.7,127.4,127.1,125.2,124.0, 123.7,121.7,121.3,119.5,119.1,116.9,115.7,115.2,111.6,97.0.HRMS (ESI)m/z calculated for C 26 H 18 ClN 2 S + [M+H] + 425.0874,found 425.0877.
Example 30: preparation of 10- (2- (3-bromophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-18))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (3-bromophenyl) indolizine and the yield of 10- (2- (3-bromophenyl) indolizin-3-yl) -10H-phenothiazine is 77%.
1 H NMR(500MHz,CDCl 3 )δ7.97(t,J＝1.8Hz,1H),7.79(d,J＝7.0 Hz,1H),7.73-7.68(m,1H),7.52-7.45(m,1H),7.35-7.33(m,1H),7.17(t,J＝ 7.9Hz,1H),7.09-7.07(m,2H),6.88-6.78(m,6H),6.56-6.53(m,1H), 6.03-6.01(m,2H). 13 C NMR(125MHz,CDCl 3 )δ141.6,136.1,131.1,130.5, 130.3,123.0,127.7,127.1,125.6,123.8,123.7,123.0,121.7,121.3,119.6, 119.1,116.9,115.7,111.6,96.9.HRMS(ESI)m/z calculated for C 26 H 18 BrN 2 S + [M+H] + 469.0369,found 469.0370.
Example 31: preparation of 10- (2- (3,4-dimethoxyphenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-19))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (3,4-dimethoxyphenyl) indolizine and the yield of 10- (2- (3,4-dimethoxyphenyl) indolizin-3-yl) -10H-phenothiazine is 84%.
1 H NMR(500MHz,CDCl 3 )δ7.81-7.75(m,1H),7.48(d,J＝8.9Hz, 1H),7.40-7.33(m,2H),7.04(dd,J＝7.4,1.7Hz,2H),6.90-6.77(m,7H), 6.51(td,J＝7.0,1.0Hz,1H),6.04-6.02m,2H),3.86(s,3H),3.71(s,3H). 13 C NMR(125MHz,CDCl 3 )δ149.0,148.2,141.5,131.1,127.8,126.9,126.8, 125.1,123.6,121.5,120.6,119.5,119.2,118.7,115.8,115.7,111.5,111.1, 110.4,96.6,55.9,55.6.HRMS(ESI)m/z calculated for C 28 H 23 N 2 O 2 S + [M+H] + 451.1475,found 451.1473.
Example 32: preparation of 10- (2- (3,4-dichlorophenyl) indolizin-3-yl) -10H-phenothiazine (formula (I-20))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (3,4-dichlorophenyl) indolizine and the yield of 10- (2- (3,4-dichlorophenyl) indolizin-3-yl) -10H-phenothiazine is 79%.
1 H NMR(400MHz,CDCl 3 )δ7.90(d,J＝2.1Hz,1H),7.78(d,J＝7.0 Hz,1H),7.62-7.60(m,1H),7.53-7.47(m,1H),7.37(d,J＝8.4Hz,1H), 7.10-7.07(m,2H),6.91-6.78(m,6H),6.58-6.54(m,1H),6.01-6.98(m,2H). 13 C NMR(101MHz,CDCl 3 )δ141.5,134.1,132.8,131.2,130.9,129.1,127.8, 127.2,126.3,123.9,122.9,121.7,121.3,119.6,119.3,117.0,115.5,115.1, 111.8,96.8.HRMS(ESI)m/z calculated for C 26 H 17 Cl 2 N 2 S + (M+H) + 459.0484, found 459.0482.
Example 33: preparation of 10- (8-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-21))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 8-methyl-2-phenylindolizine and the yield of 10- (8-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine is 86%.
1 H NMR(500MHz,CDCl 3 )δ7.84-7.82(m,2H),7.74(d,J＝6.9Hz, 1H),7.35(t,J＝7.7Hz,2H),7.24(d,J＝7.4Hz,1H),7.07-7.05(m,2H),6.90 (s,1H),6.85-6.77(m,4H),6.63(d,J＝6.5Hz,1H),6.48(t,J＝6.8Hz,1H), 6.10-6.08(m,2H),2.53(s,3H). 13 C NMR(125MHz,CDCl 3 )δ141.8,134.1, 131.9,128.9,128.4,127.7,127.2,127.0,126.9,125.1,123.5,121.1,119.7, 118.1,116.9,115.9,111.5,95.4,17.9.HRMS(ESI)m/z calculated for C 27 H 21 N 2 S + [M+H] + 405.1420,found 405.1418.
Example 34: preparation of 10- (7-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-22))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 7-methyl-2-phenylindolizine and the yield of 10- (7-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine is 90%.
1 H NMR(400MHz,CDCl 3 )δ7.85-7.80(m,2H),7.76(d,J＝7.1Hz, 1H),7.40-7.33(m,2H),7.28-7.21(m,2H),7.11-7.06(m,2H),6.89-6.78(m, 5H),6.40-6.38(m,1H),6.13-6.10(m,2H),2.34(s,3H). 13 C NMR(101MHz, CDCl 3 )δ141.8,134.1,131.4,129.0,128.9,127.7,127.1,127.0,126.9,125.3, 123.5,121.2,121.1,117.4,115.9,115.7,114.0,95.2,21.2.HRMS(ESI)m/z calculated for C 27 H 21 N 2 S + (M+H) + 405.1420,found 405.1418.
Example 35: preparation of 10- (6-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-23)))
The reaction procedure is as in example 1, except that the 2-phenylindolizine is replaced by 6-methyl-2-phenylindolizine and the yield of 10- (6-methyl-2-phenylindolizin-3-yl) -10H-phenothiazine is 85%.
1 H NMR(500MHz,CDCl 3 )δ7.81-7.79(m,2H),7.63(s,1H),7.41(d,J ＝9.0Hz,1H),7.34(t,J＝7.7Hz,2H),7.23-7.20(m,1H),7.08-7.06(m,2H), 6.86-6.80(m,5H),6.67(d,J＝8.8Hz,1H),6.11-6.09(m,2H),2.19(d,J＝ 0.6Hz,3H). 13 C NMR(125MHz,CDCl 3 )δ141.7,134.1,130.0,129.5,128.9, 127.7,127.1,126.9,125.1,123.5,122.2,121.1,120.9,119.0,118.9,116.2, 115.9,115.3,18.8.HRMS(ESI)m/z calculated for C 27 H 21 N 2 S + [M+H] + 405.1420,found 405.1415.
Example 36: preparation of 10- (7-bromo-2-phenylindolizin-3-yl) -10H-phenothiazine (formula (I-24))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 7-bromo-2-phenylindolizine and the yield of 10- (7-bromo-2-phenylindolizin-3-yl) -10H-phenothiazine is 68%.
1 H NMR(400MHz,CDCl 3 )δ7.78(d,J＝1.2Hz,1H),7.62-7.54(m, 3H),7.36(t,J＝7.4Hz,2H),7.33-7.28(m,1H),7.02-6.98(m,2H),6.86-6.77 (m,5H),6.67-6.64(m,1H),5.96-5.94(m,2H). 13 C NMR(101MHz,CDCl 3 ) δ141.5,131.5,129.6,129.4,128.6,128.0,127.7,127.1,126.2,123.8,122.6, 120.7,120.4,117.9,115.9,115.2,113.4,85.6.HRMS(ESI)m/z calculated for C 26 H 18 BrN 2 S + [M+H] + 469.0369,found 469.0364.
Example 37: preparation of 10- (2- (4-chlorophenyl) -7-methylindolizin-3-yl) -10H-phenothiazine (formula (I-25))
The reaction procedure is as in example 1, except that 2-phenylindolizine is replaced by 2- (4-chlorophenyl) -7-methylindolizine and 10- (2- (4-chlorophenyl) -7-methylindolizin-3-yl) -10H-phenothiazine is obtained in a yield of 75%.
1 H NMR(400MHz,CDCl 3 )δ7.78-7.70(m,3H),7.36-7.29(m,3H), 7.10-7.08(m,2H),6.89-6.80(m,4H),6.74(s,1H),6.41-6.39(m,1H), 6.08-6.05(m,2H),2.34(s,3H). 13 C NMR(101MHz,CDCl 3 )δ141.7,132.7, 132.6,131.5,129.5,129.0,128.3,127.7,127.0,124.1,123.6,121.2,121.1, 117.48,115.9,115.7,114.2,95.1,21.2.HRMS(ESI)m/z calculated for C 27 H 20 ClN 2 S + [M+H] + 439.1030,found 439.1032.
Example 38: preparation of 10- (2- (naphthalen-2-yl) indolizin-3-yl) -10H-phenothiazine (formula (I-26))
The reaction procedure was the same as in example 1, except that 2-phenylindolizine was changed to 2- (naphthalen-2-yl) indolizine, and the yield of 10- (2- (naphthalen-2-yl) indolizin-3-yl) -10H-phenothiazine (formula 26) was 73%.
1 H NMR(500MHz,CDCl 3 )δ8.41(d,J＝1.0Hz,1H),7.99-7.97(m, 1H),7.89-7.76(m,4H),7.54(d,J＝9.0Hz,1H),7.48-7.40(m,2H),7.13-7.11 (m,2H),7.08(s,1H),6.89-6.78(m,5H),6.57-6.54(m,1H),6.17-6.15(m, 2H). 13 C NMR(125MHz,CDCl 3 )δ141.8,133.7,132.6,131.3,131.2,128.5, 128.4,127.8,127.6,127.0,126.1,126.0,125.9,125.5,125.2,123.7,121.6, 121.3,119.4,118.8,117.0,115.9,111.4,97.1.HRMS(ESI)m/z calculated for C 30 H 21 N 2 S + [M+H] + 441.1420,found 441.1416.

Claims (6)

1. A method for the direct electrochemical synthesis of triarylamine compounds, the method comprising: taking phenothiazine compounds with a structural formula shown in a formula (II) and 2-aryl indolizine compounds with a structural formula shown in a formula (III) as raw materials, adopting a three-electrode system, taking a graphite electrode or a Pt electrode as a cathode and an anode, taking 0.1mol/L silver nitrate acetonitrile solution as a reference electrode, stirring and electrolyzing in an organic solvent containing a supporting electrolyte at 15-45 ℃ and 0.1-0.3V, and separating after the reaction is finished to obtain triarylamine compounds with a structural formula shown in a formula (I); the supporting electrolyte is LiClO 4 、 n Bu 4 NBF 4 、 n Bu 4 NPF 6 Or NaClO 4 The organic solvent is N, N-dimethylformamide, acetonitrile or ethyl acetate;
Figure FDA0003886579710000011
in the formulae (I) to (III),
R 1 is H, C-C4 alkyl, halogen, C1-C2 alkoxy, nitro, cyano, trifluoromethyl or acetyl;
R 2 is phenyl, substituted phenyl, naphthyl or substituted naphthyl, and the substituent of the substituted phenyl and the substituent of the substituted naphthyl are respectively and independently selected from one of the following groups: halogen, nitro, C1-C4 alkyl or C1-C4 alkoxy;
R 3 is H, C-C4 alkyl, C1-C4 alkoxy, chlorine, bromine or fluorine.
2. The method of claim 1, wherein: r 1 Is H, cl, methoxy, methylthio, trifluoromethyl, cyano or acetyl, R 2 Is phenyl, halophenyl, alkyl-substituted phenyl, alkoxy-substituted phenyl or naphthyl, R 3 Is H, methyl or bromine.
3. The method of claim 1 or 2, wherein: the mass ratio of the phenothiazine compound to the indolizine compound is 100:80 to 150.
4. The method of claim 1 or 2, wherein: the mass concentration of the supporting electrolyte in the organic solvent is 0.05-0.15 mol/L.
5. The method of claim 1 or 2, wherein: after the reaction is finished, the solvent is evaporated under reduced pressure, and then thin layer chromatography separation is carried out, wherein the volume ratio of petroleum ether/ethyl acetate is 20:1 as developing agent, collecting thin layer containing target compound, eluting with dichloromethane, filtering, and evaporating the filtrate to remove solvent to obtain the triarylamine compound.
6. A method according to claim 1 or 2, characterized in that the method is as follows: taking phenothiazine compounds with a structural formula shown in a formula (II) and 2-aryl indolizine compounds with a structural formula shown in a formula (III) as raw materials, adopting a three-electrode system, taking a cathode and an anode as Pt electrodes, taking 0.1mol/L silver nitrate acetonitrile solution as a reference electrode, and adding 0.05-0.15 mol/LLIClO 4 Stirring and electrolyzing the N, N-dimethylformamide solution for 3.5 to 7.0 hours at the temperature of between 15 and 45 ℃ and at the pressure of between 0.1 and 0.3V, evaporating the solvent under reduced pressure, and then carrying out thin-layer chromatography separation, wherein the volume ratio of petroleum ether to ethyl acetate is 20:1 as developing agent, collecting thin layer containing target compound, eluting with dichloromethane, filtering, and evaporating the filtrate to remove solvent to obtain the triarylamine compound.
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