CN116005178B - Synthesis method of 1,2-dihydro quinazoline compound - Google Patents
Synthesis method of 1,2-dihydro quinazoline compound Download PDFInfo
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Abstract
The invention discloses a synthesis method of a 1,2-dihydro quinazoline compound, belonging to the technical field of organic chemistry. 2-sulfonamido aryl ketone 1, ammonia 2 and methanol 3 are used as raw materials, manganese chloride tetrahydrate is used as a catalyst, lithium perchlorate is used as an electrolyte, and electrochemical cyclization reaction is carried out in an organic solvent in the presence of alkali to obtain the 1,2-dihydro quinazoline compound. The invention uses low-cost and easily-obtained micromolecule ammonia as an N source, methanol as a methylene source and a solvent, and carries out multi-component continuous serial cyclization reaction with 2-sulfonylamino aryl ketone, wherein the reaction is carried out by a multi-step reaction one-pot method, an oxidant is not needed, and byproducts are only hydrogen and water, so that the method is environment-friendly; provides a new idea for synthesizing 1,2-dihydro quinazoline series products.
Description
Technical Field
The invention relates to a synthesis method of a 1,2-dihydro quinazoline compound, belonging to the technical field of organic chemistry.
Background
The 1,2-dihydro quinazoline compound and the derivative thereof are widely applied to bioactive molecules, and have important application value in the field of medicines. Such as inducible nitric oxide synthase inhibitors, have anti-inflammatory activity; butyrylcholinesterase inhibitor has the prospect of treating Alzheimer's disease.
In 1979, the literature reported that quinazoline was reduced to 1,2-dihydroquinazoline under the action of sodium borohydride and trifluoroacetic acid, however, sodium borohydride which is sensitive to water and has strong reducing capability is used with more severe requirements on reaction conditions, and functional group compatibility is poor. The use of the more acidic trifluoroacetic acid also limits its use. In 1981, the literature reported [ CF 3 C(O)O] 2 BH-TFA is used for the reduction of quinazoline, however, the reaction selectivity is poor, the reaction byproducts are more, and in addition to the product 1,2-dihydroquinazoline, the byproduct 1,2,3, 4-tetrahydroquinazoline, even the ring-opened product o-methylaminobenzylamine, can be produced. In 2009, the literature reports the microwave-promoted cyclization reaction of O-aminoarylketone O-phenyloxime and aldehyde to synthesize 1,2-dihydroquinazoline compounds, wherein the reaction of toluene as a solvent is carried out at 160 ℃. The reaction atom has poor economy, raw aldehyde does not contain formaldehyde, a C2-site non-substituent product cannot be synthesized, and the reaction temperature is high. In 2018, the literature reports that indazole salt compounds are rearranged and synthesized into 1,2-dihydroquinazoline compounds under the action of potassium carbonate. The reaction requires a carefully designed substrate, cannot synthesize a C2-position substituent-free product, and has high reaction temperature. In 2020, the synthesis of 1,2-dihydroquinazoline compounds by multi-step reactions using o-alkylaminobenzonitrile as a raw material is reported in the literature. Firstly, cyano groups of the o-alkyl amino benzonitrile are reacted with an organolithium reagent,and then adding water to obtain an imine intermediate, and reacting under NIS participation and illumination to obtain a target product. The reaction has more defects, uses organic metal reagents sensitive to air and water, has more reaction steps and complex operation, and requires extremely low temperature of-50 ℃. Therefore, the conventional synthesis method of 1,2-dihydroquinazoline has various problems and needs to be solved urgently.
The electrochemical organic synthesis method has been rapidly developed in recent years, and the electrode is utilized to realize electron loss, so that the use of an oxidant and a reducing agent is avoided, and a plurality of reactions which cannot be realized by the traditional method can be realized under mild conditions, thereby being environment-friendly. However, few examples of reactions are carried out using inexpensive readily available methanol for in situ oxidation to aldehydes under electrochemical conditions.
Therefore, the compound is synthesized by using cheaper and easily available raw materials and developing a more green, efficient and mild method.
Disclosure of Invention
In order to overcome the technical defects, the application provides a method for synthesizing the 1,2-dihydroquinazoline compounds in one step by using cheap and easily available raw materials to perform multi-component reaction. The strategy realizes the simultaneous oxidation of methanol into aldehyde and NH under the electrochemical condition for the first time 3 And (3) carrying out an organic synthesis reaction. The reaction uses 2-sulfonamido aryl ketone, low-cost and easily available micromolecular methanol and NH 3 The method is used as a reaction substrate, and the quick and efficient synthesis of the 1,2-dihydroquinazoline compound is realized in the next step of electrochemistry. However, this strategy suffers from a number of difficulties prior to implementation, such as competing reaction of the aldehyde carbonyl group with the ketocarbonyl group of the 2-sulfonylamino aryl ketone after reduction of methanol to formaldehyde, carbonyl group with NH 3 Self-coupling reactions, NH, are also possible electrochemically after imine formation 3 Can electrochemically reduce aldehyde ketone into alcohol, NH 3 Can be directly anodized to become N 2 And lost. All of the above possibilities will make the reaction incomplete. The invention takes cheap manganese chloride tetrahydrate as a catalyst, DBU as alkali, electrolyte and methanol as a solvent, and smoothly realizes the electrochemical synthesis of the 1,2-dihydroquinazoline compounds at room temperature. Mild reaction condition, simple operation, insensitivity to water and air, and no need of oxygenThe use of the chemical agent and the reducing agent solves various problems faced by the previous 1,2-dihydro quinazoline synthesis method.
The invention relates to a synthesis method of a 1,2-dihydro quinazoline compound, wherein the reaction equation is expressed as follows:
wherein: r is R 1 Selected from phenyl, C1-C4 alkyl, halophenyl, C1-C4 alkoxyphenyl; r is R 2 Selected from halogen, C1-C4 alkyl, C1-C4 alkoxy; r is R 3 Selected from the group consisting of halophenyl, C1-C4 alkylphenyl, and C1-C4 alkoxyphenyl.
The method comprises the following operations: taking 2-sulfonylamino aryl ketone 1, ammonia 2 and methanol 3 as raw materials, and carrying out constant current reaction in an organic solvent in the presence of a manganese catalyst and alkali to obtain the 1,2-dihydro quinazoline compound 4.
Further, in the above technical solution, R 1 Selected from phenyl, C1-C4 alkyl, halophenyl, methoxyphenyl; r is R 2 Selected from halogen, methyl, methoxy; r is R 3 Selected from 4-iodophenyl, 4-methylphenyl, 4-methoxyphenyl.
Further, in the above technical scheme, the ammonia 2 source is a 4-7M ammonia/methanol solution, preferably a 7M ammonia/methanol solution.
Further, in the above-described technical scheme, the electrode material is selected from the group consisting of C (+)/Pt (-), C (+)/C (-), GF (+)/Pt (-), GF (+)/GF (-), pt (+)/Pt (-), pt (+)/C (-), and preferably C (+)/Pt (-) during the constant current reaction.
Further, in the above technical scheme, the manganese catalyst is selected from manganese chloride tetrahydrate or manganese chloride, preferably manganese chloride tetrahydrate.
Further, in the technical scheme, the molar ratio of the manganese catalyst to the 2-sulfonylamino aryl ketone 1 is 0.10-0.50:1, a step of; preferably, the molar ratio of the two is 0.20:1.
further, in the above technical scheme, the base is selected from DBU, KOH or K 2 CO 3 DBU is preferred.
Further, in the above technical scheme, the solvent is selected from MeOH or DCE, preferably MeOH.
Further, in the above technical solution, the current intensity is selected from 10-20mA, preferably 15mA.
Further, in the above technical scheme, the reaction time is selected from 8 to 12 hours, preferably 10 hours.
In order to further explore the reaction mechanism, the following comparative experiments were performed, the reaction results were as follows:
comparative experiment a: from raw materials 1a and NH 3 The reaction synthesised the possible imine intermediate 5, and found that placing intermediate 5 in the optimal reaction conditions did not give product 4a. Thus, imines are not intermediates for the reaction. The reaction results are shown below:
based on the above results and the reports in the prior art, taking the ring-closing reaction of raw material 1a, ammonia 2 and methanol 3 to produce product 4a as an example, the possible mechanism of the reaction is presumed to be as follows:
on the anode, the catalyst divalent manganese is oxidized into trivalent manganese, the trivalent manganese in turn oxidizes methanol into formaldehyde, and the formaldehyde is then mixed with NH 3 The effect becomes imine intermediate II. The raw material 1a removes hydrogen on NH under the action of alkali to become N negative ions, and then attacks the imine intermediate II to generate a new N negative ion intermediate IV. N negative ions attack the intramolecular ketocarbonyl group to finish ring closure, and an intermediate V is obtained. The oxygen anions in V become hydroxyl after obtaining hydrogen, and then the hydroxyl is dehydrated with the hydrogen on N to obtain the target product 4a.
The invention has the beneficial effects that:
the invention uses 2-sulfonylamino aryl ketone, low-cost micromolecular methanol and NH 3 Takes the methanol as raw material, realizes the oxidation of the methanol under the condition of no oxidant and mild conditionIs formaldehyde and then reacts with NH 3 And (3) dehydrating to generate imine in situ, and then further reacting with amino and carbonyl of 2-sulfonylamino aryl ketone to close the ring, so as to obtain the 1,2-dihydro quinazoline compound through high-efficiency and rapid synthesis.
The invention overcomes the defects of the prior 1,2-dihydroquinazoline synthesis method and various difficulties possibly encountered by the electrochemical reaction, realizes the ordered activation and the ordered combination among multiple components, and has high innovation. The byproducts are only water and hydrogen, so that the method is environment-friendly. Provides a brand new synthetic strategy for synthesizing 1,2-dihydro quinazoline series products.
Detailed Description
Example 1
Optimization of reaction conditions
Compound 1a (0.2 mmol) and LiClO were first prepared 4 (0.2 mmol) and manganese catalyst were added to a 10mL diaphragm-free electrolyzer, followed by addition of base, NH 3 (7M in MeOH,0.5 mL) and organic solvent (4.5 mL). The bottle mouth is plugged by a rubber plug inserted into the electrode. The power supply was set at 15 milliamp constant current and reacted at room temperature for 10 hours. The solvent is removed by a rotary evaporator, and the target product is obtained by column chromatography separation.
The optimized reaction results were as follows:
in the reaction condition screening process, the influence of electrode materials (reference numerals 1 to 6), manganese catalysts and the amounts thereof (reference numerals 7 to 10), bases (reference numerals 11 to 12), organic solvents (13 to 17), current intensities (reference numerals 18 to 19), reaction times (reference numerals 20 to 21) and the like were examined. Finally, the optimal electrode material is C (+)/Pt (-), and the optimal catalyst is MnCl 2 ·4H 2 O, the optimal catalyst amount is 20mol%, the optimal base is DBU, the optimal solvent is MeOH, the optimal current intensity is 15mA, and the optimal reaction time is 10 hours.
Example 2:
compound 1a (0.2 mmol) and MnCl were first reacted 2 ·4H 2 O(0.04mmol)、LiClO 4 (0.2 mmol) was added to a 10mL non-membrane electrolyzer, followed by addition of liquid DBU (0.2 mmol), NH 3 (7M in MeOH,0.5 mL) and MeOH (4.5 mL). The bottle mouth was plugged with a rubber stopper after the electrode was inserted, and the electrode used was a carbon electrode (6 mm diameter carbon rod) and a platinum electrode (1 cm. Times.1 cm platinum sheet). The power supply was connected to the electrode, carbon was the anode, platinum was the cathode, the current intensity was set to 15mA, and then current was applied. The reaction was carried out at room temperature for 10 hours. Reaction end rotary evaporator to remove solvent, petroleum ether: ethyl acetate=9: column chromatography with eluent 1 gave 61.8mg of product 4a as colorless liquid in 85% yield. 1 H NMR(600MHz,CDCl 3 )δ7.86(d,J＝7.8Hz,1H),7.56(t,J＝7.8Hz,1H),7.38(t,J＝7.2Hz,1H),7.35(d,J＝7.2Hz,2H),7.28(t,J＝7.8Hz,2H),7.24(t,J＝7.8Hz,1H),7.09(d,J＝7.2Hz,1H),6.95(d,J＝8.4Hz,4H),5.48(s,2H),2.19(s,3H). 13 C NMR(151MHz,CDCl 3 )δ165.9,143.9,138.1,136.5,135.6,132.3,129.9,129.3,128.7,128.1,128.0,127.8,127.0,126.7,125.5,63.3,21.4.
Example 3:
according to the reaction conditions of example 2, only the structure of substrate 1 was changed, and the reaction results were as follows: 4- (4-fluorobenzyl) -1-tosyl-1,2-dihydroquinazoline (4 b): white solid;62.9mg,83% yield; 1 H NMR(600MHz,CDCl 3 )δ7.86(d,J＝7.8Hz,1H),7.57(t,J＝7.8Hz,1H),7.34(d,J＝8.4Hz,2H),7.25(dd,J＝7.2,1.2Hz,1H),7.07(dd,J＝7.8,1.2Hz,1H),6.98(d,J＝6.0Hz,4H),6.95(d,J＝8.4Hz,2H),5.46(s,2H),2.20(s,3H). 13 C NMR(151MHz,CDCl 3 )δ164.7,164.6,162.9,143.9,138.1,135.7,132.8,132.8,132.4,130.8,130.7,129.3,127.8,127.8,127.1,126.7,125.3,115.1,115.0,63.4,21.4. 19 F NMR(565MHz,CDCl 3 )δ-110.64.
4-(4-chlorophenyl)-1-tosyl-1,2-dihydroquinazoline(4c):White solid；69.2mg,87％yield； 1 H NMR(600MHz,CDCl 3 )δ7.88(d,J＝8.4Hz,1H),7.59(t,J＝7.8Hz,1H),7.36(d,J＝8.4Hz,2H),7.28(d,J＝8.4Hz,3H),7.08(d,J＝7.8Hz,1H),6.98(d,J＝7.8Hz,2H),6.94(d,J＝8.4Hz,2H),5.49(s,2H),2.23(s,3H). 13 C NMR(151 MHz,CDCl 3 )δ164.7,144.0,138.1,136.0,135.7,135.1,132.5,130.1,129.3,128.3,127.9,127.7,127.2,126.8,125.2,63.4,21.5.
4-(4-methoxyphenyl)-1-tosyl-1,2-dihydroquinazoline(4d):White solid；58.4 mg,74％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.85(d,J＝8.4 Hz,1H),7.55(t,J＝7.8 Hz,1H),7.34(d,J＝7.8 Hz,2H),7.24(d,J＝7.2 Hz,1H),7.13(d,J＝7.8 Hz,1H),6.94(t,J＝7.2 Hz,4H),6.80(d,J＝8.4 Hz,2H),5.44(s,2H),3.83(s,3H),2.19(s,3H). 13 C NMR(151 MHz,CDCl 3 )δ165.1,161.0,143.8,138.2,135.7,132.1,130.4,129.3,129.2,128.1,127.9,127.0,126.6,125.7,113.3,63.4,55.5,21.5.
4-methyl-1-tosyl-1,2-dihydroquinazoline(4e):White solid；45.7 mg,76％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.76(d,J＝8.4 Hz,1H),7.52(t,J＝8.4 Hz,1H),7.30(d,J＝7.8 Hz,4H),7.08(d,J＝7.8 Hz,2H),5.27(s,2H),2.33(s,3H),1.87(s,3H). 13 C NMR(151 MHz,CDCl 3 )δ163.3,143.9,136.9,135.8,132.1,129.2,127.7,127.0,126.7,126.0,125.4,62.8,21.6,21.6.
4-ethyl-1-tosyl-1,2-dihydroquinazoline(4f):White solid；49.2 mg,78％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.79(d,J＝8.4 Hz,1H),7.52-7.49(m,1H),7.33-7.29(m,4H),7.07(d,J＝8.4 Hz,2H),5.30(d,J＝1.6 Hz,2H),2.31(s,3H),2.28(q,J＝7.8 Hz,2H),0.68(t,J＝7.8 Hz,3H). 13 CNMR(151 MHz,CDCl 3 )δ166.8,143.9,137.0,136.2,131.9,129.3,127.6,126.9,126.9,125.3,125.0,62.9,27.6,21.5,10.2.
6-chloro-4-phenyl-1-tosyl-1,2-dihydroquinazoline(4g):White solid；53.8 mg,68％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.80(d,J＝8.4 Hz,1H),7.52(dd,J＝9.0,2.4 Hz,1H),7.40(t,J＝7.8 Hz,1H),7.36(d,J＝8.4 Hz,2H),7.31(t,J＝7.8 Hz,2H),7.07(d,J＝2.4 Hz,1H),6.99(d,J＝7.8 Hz,2H),6.95(d,J＝7.2 Hz,2H),5.48(s,2H),2.20(s,3H). 13 CNMR(151 MHz,CDCl 3 )δ164.7,144.2,136.5,136.0,135.4,132.4,132.3,130.2,129.5,128.6,128.5,128.2,127.8,127.8,126.6,63.4,21.4.6-bromo-4-phenyl-1-tosyl-1,2-dihydroquinazoline(4h):White solid；55.3 mg,63％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.75(d,J＝9.0 Hz,1H),7.67(dd,J＝9.0,2.4 Hz,1H),7.41(t,J＝7.2 Hz,1H),7.37(d,J＝7.8 Hz,2H),7.31(t,J＝7.8 Hz,2H),7.22(d,J＝1.8 Hz,1H),7.00(d,J＝7.8 Hz,2H),6.95(d,J＝7.8 Hz,2H),5.49(s,2H),2.21(s,3H). 13 CNMR(151 MHz,CDCl 3 )δ164.6,144.3,137.1,136.0,135.4,135.2,130.7,130.2,129.5,128.8,128.6,128.2,127.8,126.9,120.2,63.4,21.5.7-methyl-4-phenyl-1-tosyl-1,2-dihydroquinazoline(4i):White solid；57.1 mg,76％yield； 1 H NMR(600 MHz,CDCl 3 )δ7.68(s,1H),7.37(d,J＝8.4 Hz,3H),7.28(t,J＝7.8 Hz,2H),7.05(d,J＝7.8 Hz,1H),6.98(d,J＝7.8 Hz,1H),6.96(d,J＝7.2 Hz,4H),5.45(s,2H),2.48(s,3H),2.19(s,3H). 13 C NMR(151 MHz,CDCl 3 )δ165.8,143.9,143.2,138.0,136.8,135.8,129.8,129.3,128.8,127.9,127.8,127.5,127.3,123.1,63.5,22.0,21.4.
6,7-dimethoxy-4-phenyl-1-tosyl-1,2-dihydroquinazoline(4j):White solid；65.1mg,77％yield； 1 H NMR(600MHz,CDCl 3 )δ7.37(d,J＝9.0Hz,4H),7.28(t,J＝7.8Hz,2H),6.96(d,J＝7.8Hz,4H),6.51(s,1H),5.43(s,2H),4.04(s,3H),3.69(s,3H),2.19(s,3H). 13 C NMR(151MHz,CDCl 3 )δ165.2,152.1,147.4,143.9,136.9,135.5,132.5,129.8,129.3,128.7,128.0,127.9,118.6,109.9,109.6,63.6,56.6,56.2,21.5.
1-((4-iodophenyl)sulfonyl)-4-phenyl-1,2-dihydroquinazoline(4k):White solid；58.2mg,61％yield； 1 H NMR(600MHz,CDCl 3 )δ7.85(d,J＝8.4Hz,1H),7.58(t,J＝8.4Hz,1H),7.50(d,J＝7.8Hz,2H),7.42(t,J＝7.8Hz,1H),7.37(t,J＝7.8Hz,2H),7.28(d,J＝7.2Hz,1H),7.17(d,J＝8.4Hz,2H),7.12(d,J＝7.8Hz,1H),6.95(d,J＝7.2Hz,2H),5.49(s,2H). 13 C NMR(151MHz,CDCl 3 )δ166.1,138.2,137.9,137.7,136.4,132.5,130.1,129.3,128.6,128.4,128.3,127.1,127.0,125.6,100.9,63.5.1-((4-methoxyphenyl)sulfonyl)-4-phenyl-1,2-dihydroquinazoline(4l):White solid；55.7mg,74％yield； 1 H NMR(600MHz,CDCl 3 )δ7.85(d,J＝7.8Hz,1H),7.55(t,J＝7.8Hz,1H),7.38(t,J＝9.0Hz,3H),7.29(t,J＝7.2Hz,2H),7.24(t,J＝7.8Hz,1H),7.11(d,J＝7.8Hz,1H),7.00(d,J＝7.2Hz,2H),6.60(d,J＝8.4Hz,2H),5.48(s,2H),3.63(s,3H). 13 CNMR(151MHz,CDCl 3 )δ165.8,163.2,138.2,136.7,132.3,130.1,130.0,129.9,128.8,128.0,128.0,127.0,126.6,125.6,113.9,63.5,55.5.
the foregoing embodiments illustrate the basic principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the above-described embodiments, and that the above-described embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the scope of the principles of the invention, which are defined in the appended claims.
Claims (5)
1. The synthesis method of the 1,2-dihydro quinazoline compound is characterized by comprising the following operations: taking 2-sulfonylamino aryl ketone 1, ammonia 2 and methanol 3 as raw materials, and carrying out constant current reaction in an organic solvent in the presence of a manganese catalyst and alkali to obtain a 1,2-dihydro quinazoline compound 4; the reaction equation is expressed as follows:
wherein: r is R 1 Selected from phenyl, C1-C4 alkyl, halophenyl, C1-C4 alkoxyphenyl; r is R 2 Selected from halogen, C1-C4 alkyl, C1-C4 alkoxy; r is R 3 Selected from the group consisting of halophenyl, C1-C4 alkylphenyl, C1-C4 alkoxyphenyl; in the constant current reaction, an electrode material is selected from C (+)/Pt (-), C (+)/C (-), GF (+)/Pt (-), GF (+)/GF (-) or Pt (+)/Pt (-); the manganese catalyst is selected from tetrahydrate manganese chloride or manganese chloride; the molar ratio of the manganese catalyst to the 2-sulfonylamino aryl ketone 1 is 0.10-0.50:1, a step of; the base is selected from DBU, KOH or K 2 CO 3 The method comprises the steps of carrying out a first treatment on the surface of the The organic solvent is selected from MeOH or DCE.
2. According to claim 1The synthesis method of the 1,2-dihydro quinazoline compound is characterized by comprising the following steps: r is R 1 Selected from phenyl, C1-C4 alkyl, halophenyl, methoxyphenyl; r is R 2 Selected from halogen, methyl, methoxy; r is R 3 Selected from 4-iodophenyl, 4-methylphenyl, 4-methoxyphenyl.
3. The method for synthesizing a 1,2-dihydroquinazoline compound according to claim 1, wherein: the ammonia 2 source is 4-7M ammonia/methanol solution.
4. The method for synthesizing a 1,2-dihydroquinazoline compound according to claim 1, wherein: the current intensity is 10-20mA.
5. The method for synthesizing a 1,2-dihydroquinazoline compound according to any one of claims 1 to 4, wherein: the reaction time is 8-12 hours.
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