CN113979943A - 3-fluoro-5H-indeno [1,2-b ] pyridine compound and synthetic method thereof - Google Patents

3-fluoro-5H-indeno [1,2-b ] pyridine compound and synthetic method thereof Download PDF

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CN113979943A
CN113979943A CN202111448226.4A CN202111448226A CN113979943A CN 113979943 A CN113979943 A CN 113979943A CN 202111448226 A CN202111448226 A CN 202111448226A CN 113979943 A CN113979943 A CN 113979943A
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indeno
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王治明
李金山
吴海建
杨健国
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Taizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes

Abstract

The invention discloses a 3-fluoro-5H-indeno [1,2-b ] pyridine compound and a synthetic method thereof, wherein the synthetic method comprises the following steps: under the action of acid, the aza-diene compound and difluoroenol silyl ether compound react in an organic solvent, after the reaction is finished, alkali is added for treatment, and then the 3-fluoro-5H-indeno [1,2-b ] pyridine compound is obtained through separation. The method has simple operation, high yield and higher activity of the obtained product.

Description

3-fluoro-5H-indeno [1,2-b ] pyridine compound and synthetic method thereof
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a 3-fluoro-5H-indeno [1,2-b ] pyridine compound and a synthesis method thereof.
Background
The 3-fluoro-5H-indeno [1,2-b ] pyridine compound is a special organic molecular structure framework in heterocyclic chemistry, has wide bioactivity, and has important research value and certain application prospect in pharmaceutical chemistry. Among them, many compounds containing the above core structural units have remarkable biological activity and excellent optical properties, and thus have potential application values in pharmaceutical chemistry and material chemistry (formula I). The existing method for synthesizing the compounds mainly comprises a synthetic route of 'Michelal addition-intramolecular condensation' starting from alpha, beta-unsaturated ketone, alpha-benzotriazolyl ketone and ammonium salt, a synthetic route of 'Michelal addition-hetero Wittig reaction' starting from aza Wittig reagent and alpha, beta-unsaturated ketone, a synthetic route of 'Claisen condensation-Michelal addition' starting from 1-indanone, aromatic aldehyde, pyridinium and ammonium salt, and the like. However, the above synthetic routes have the disadvantages of long synthetic route, low reaction yield, low atom utilization rate and the like. Meanwhile, a method for obtaining the 3-fluoro-5H-indeno [1,2-b ] pyridine compound by one step of series reaction from simple and easily available raw materials is not reported at present.
Figure BDA0003377986260000021
Due to the physicochemical properties of fluorine-containing functional groups, organic fluorine-containing compounds are widely used in many scientific fields such as life, medicine, and materials. Statistically, more than 20% of the drug molecules have fluorine-containing functional groups including fluorine atom (F) and difluoromethyl (CHF)2) Trifluoromethyl (CF)3) Trifluoromethoxy group (OCF)3) And trifluoromethylthio (SCF)3) And the like. However, the amount of the fluorine-containing organic compounds existing in nature is very limited, and cannot meet the requirements of daily production and life of human beings, so most of the common organic fluorine-containing compounds need to be obtained by artificial synthesis. The synthesis method of directly replacing hydrogen atoms with fluorine atoms is one of five chemical transformations of cumin by chemists, and is concerned by the chemists. Therefore, through the design concept of the series reaction, the 3-fluoro-5H-indeno [1,2-b ] is synthesized simply, efficiently, greenly and accurately]The pyridine compounds have important practical significance.
Disclosure of Invention
The invention provides a 3-fluoro-5H-indeno [1,2-b ] pyridine compound, a synthesis method and application thereof, wherein the 3-fluoro-5H-indeno [1,2-b ] pyridine compound has certain pharmaceutical activity, and the synthesis method is simple to operate and high in yield.
The technical scheme of the invention is as follows:
a3-fluoro-5, 6-dihydrobenzo [ h ] quinoline compound has the following structural formula:
Figure BDA0003377986260000031
wherein R is1Independently selected from H, C1～C4Alkyl or halogen;
Ar1is substituted or unsubstituted aryl or heteroaryl, and the substituent on the aryl or heteroaryl is selected from phenyl and C1～C4Alkyl radical, C1～C4One or more of alkoxy and halogen, and the number of carbon atoms of the aryl or heteroaryl is 12 or less;
Ar2is a substituted or unsubstituted aryl group, and the substituent on the aryl group is selected from C1～C4Alkyl radical, C1～C4One or more of alkoxy, phenyl, halogen and hydroxyl, wherein the number of carbon atoms of the aryl is less than or equal to 12.
Preferably, R is1Independently selected from H, methyl or F;
ar is1Is substituted or unsubstituted phenyl or thienyl, and the substituent on the phenyl or the thienyl is selected from one or two of methyl, methoxy, tert-butyl, phenyl, F, Cl and Br;
ar is1Is substituted or unsubstituted phenyl, and the substituent on the phenyl is selected from one or more of methyl, methoxy, phenyl, F, Cl and hydroxyl.
Preferably, the 3-fluoro-5H-indeno [1,2-b ] pyridine compound is further selected from one of the following specific compounds:
Figure BDA0003377986260000041
the invention also provides a preparation method of the 3-fluoro-5H-indeno [1,2-b ] pyridine compound, which comprises the following steps:
under the action of acid, reacting an aza-diene compound and a difluoroenol silyl ether compound in an organic solvent, adding alkali for treatment after the reaction is finished, and separating to obtain the 3-fluoro-5H-indeno [1,2-b ] pyridine compound;
the structure of the aza-diene compound is shown as the formula (I):
Figure BDA0003377986260000042
the structure of the difluoroenol silyl ether compound is shown as the formula (II):
Figure BDA0003377986260000043
in the formulae (I) and (II), R1、Ar1And Ar2Is as defined in any one of claims 1 to 3.
Preferably, the acid is TfOH.
Preferably, the organic solvent is 1, 2-dichloroethane.
Preferably, the molar ratio of the aza-diene compound to the difluoroenol silyl ether compound to the acid is 1: 1.1-1.3: 1.9 to 2.1.
Preferably, the reaction temperature is 60 to 90 ℃ and the reaction time is 4 to 12 hours.
Preferably, the base is ethylenediamine or sodium hydroxide.
Compared with the prior art, the invention has the beneficial effects that:
according to the synthesis method, the target compound is synthesized by taking the aza-diene and the difluoroenol silyl ether as starting raw materials and adopting a series reaction of five-step reaction and one-pot method, the raw materials are simple and easy to obtain, the operation is simple, the yield and the reaction selectivity are high, and the product obtained according to the method has certain activity.
Detailed Description
EXAMPLES 1 to 14 Condition optimization experiments
In a 10mL Schlenk tube, aza diene 1a (0.5mmol), difluoroenol silyl ether 2a (0.6mmol), Lewis acid or protonic acid (0.5-1.5 mmol), a reaction solvent (2.5mL) are added, and the mixture is stirred and reacted at 60-90 ℃ for 4-12 hours. The reaction was then cooled to room temperature, to which was added ethylenediamine (3 drops) and aqueous sodium hydroxide (1.0M, 2.5mL) and stirred, extracted with dichloroethane (3 × 3mL), the organic phases combined, dried over anhydrous sodium sulfate, sand-core filtered, the solvent concentrated, and chromatographed with petroleum ether/ethyl acetate-45/1 to give the desired product 3 a.
The reaction formula is as follows:
Figure BDA0003377986260000061
Figure BDA0003377986260000062
examples 15 to 20 Synthesis of Compounds 3b to 3g
In a 10mL Schlenk tube, aza-diene 1(0.5mmol), difluoroenolsilyl ether 2(0.6mmol), trifluoromethanesulfonic acid (TfOH, 1.5mmol), dichloroethane (DCE, 2.5mL) were added and the reaction was stirred at 90 ℃ for 4-8 h (reaction time monitored by TLC). The reaction was then cooled to room temperature, to which were added ethylenediamine (3 drops) and aqueous sodium hydroxide (1.0M, 2.5mL) and stirred, extracted with dichloroethane (3 × 3mL), the organic phases combined, dried over anhydrous sodium sulfate, sand core filtered, the solvent concentrated, and the column chromatographed with petroleum ether/ethyl acetate (50/1-40/1) to give the desired products 3 b-3 g.
The equations and results are as follows:
Figure BDA0003377986260000071
the characterization data of the products obtained in the examples are as follows:
3-fluoro-2,4-diphenyl-5H-indeno[1,2-b]pyridine(3a):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1to 40/1,v/v)as eluent to give compound3a(white solid,126.4mg,75％yield).M.p.:182–183℃；1H NMR(400MHz,CDCl3)δ8.17(d,J＝7.5Hz,1H),8.10–8.08(m,2H),7.60–7.44(m,10H),7.44–7.38(m,1H),3.89(s,2H)；19F NMR(376MHz,CDCl3)δ–133.90(s,1F)；13C NMR(100MHz,CDCl3)δ156.2(d,J＝4.8Hz),153.5(d,J＝256.9Hz),145.3(d,J＝14.5Hz),143.9(d,J＝2.0Hz),140.5,136.1(d,J＝5.1Hz),136.0,134.9(d,J＝16.8Hz),132.4,129.2(d,J＝1.2Hz),129.1(d,J＝6.0Hz),128.9(d,J＝7.0Hz),128.7,128.4,128.4,127.4,125.0,121.0,34.2(d,J＝1.7Hz)；HRMS(ESI)calcd for[C24H17FN(M+H)+]:338.1345,found:m/z 338.1350.
4-(2-chlorophenyl)-3-fluoro-2-phenyl-5H-indeno[1,2-b]pyridine(3b):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3b(white solid,133.0mg,72％yield).M.p.:138–139℃；1H NMR(400MHz,CDCl3)δ8.18(d,J＝7.5Hz,1H),8.12–8.09(m,2H),7.59(dd,J＝6.5,1.9Hz,1H),7.55–7.49(m,3H),7.43(dddd,J＝12.3,8.5,6.9,2.6Hz,6H),3.82–3.67(m,2H)；19F NMR(376MHz,CDCl3)δ–130.73(s,1F)；13C NMR(100MHz,CDCl3)δ156.1(d,J＝4.7Hz),153.6(d,J＝257.6Hz),145.0(d,J＝13.8Hz),143.9(d,J＝1.6Hz),140.5,136.7,136.0(d,J＝5.3Hz),133.2,132.7(d,J＝18.5Hz),131.7,130.6,130.3,130.0,129.1(d,J＝6.0Hz),129.0,128.5,128.4,127.4,127.0,125.1,121.1,33.8(d,J＝1.7Hz)；HRMS(ESI)calcd for[C24H16FClN(M+H)+]:372.0955,found:m/z 372.0961.
3-fluoro-2,4-diphenyl-5,6-dihydrobenzo[h]quinoline(3c):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3c(white solid,150.7mg,86％yield).M.p.:193–194℃；1H NMR(400MHz,CDCl3)δ8.48(d,J＝7.7Hz,1H),8.15(d,J＝7.4Hz,2H),7.52(dd,J＝14.1,7.0Hz,5H),7.48–7.44(m,1H),7.39(dd,J＝15.0,7.5Hz,3H),7.33(t,J＝7.4Hz,1H),7.23(d,J＝7.3Hz,1H),2.89–2.86(m,2H),2.83–2.78(m,2H)；19F NMR(376MHz,CDCl3)δ–128.90(s,1F)；13C NMR(100MHz,CDCl3)δ153.9(d,J＝259.3Hz),148.2(d,J＝5.5Hz),143.0(d,J＝12.9Hz),137.4,136.8(d,J＝16.0Hz),136.0(d,J＝5.9Hz),134.6,132.4(d,J＝1.0Hz),130.9,129.5,128.9,128.8(d,J＝2.9Hz),128.5,128.3,127.5,127.2,125.4,27.9,25.5；HRMS(ESI)calcd for[C25H19FN(M+H)+]:352.1502,found:m/z 352.1497.
3-fluoro-2-phenyl-4-(p-tolyl)-5,6-dihydrobenzo[h]quinoline(3d):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3d(white solid,150.5mg,82％yield).M.p.:157–158℃；1H NMR(400MHz,CDCl3)δ8.46(d,J＝7.0Hz,1H),8.15–8.11(m,2H),7.49(t,J＝7.4Hz,2H),7.44–7.36(m,2H),7.31(dd,J＝11.8,4.5Hz,3H),7.25(d,J＝8.4Hz,2H),7.21(d,J＝7.3Hz,1H),2.88–2.78(m,4H),2.44(s,3H)；19F NMR(376MHz,CDCl3)δ–128.94(s,1F)；13C NMR(100MHz,CDCl3)δ154.0(d,J＝259.0Hz),148.2(d,J＝5.4Hz),143.0(d,J＝13.0Hz),138.3,137.4,136.8(d,J＝15.7Hz),136.1(d,J＝5.9Hz),134.6,131.0,129.4,129.3(d,J＝1.0Hz),129.2,128.9,128.9,128.8,128.3,127.5,127.1,125.4,27.9,25.5,21.4；HRMS(ESI)calcd for[C26H21FN(M+H)+]:366.1658,found:m/z 366.1659.
3-fluoro-4-(4-fluorophenyl)-2-phenyl-5,6-dihydrobenzo[h]quinoline(3e):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3e(white solid,171.1mg,93％yield).M.p.:152–153℃；1H NMR(400MHz,CDCl3)δ8.47(dd,J＝7.7,1.0Hz,1H),8.14(dd,J＝7.0,1.3Hz,2H),7.54–7.49(m,2H),7.47–7.42(m,1H),7.40(dd,J＝7.6,1.1Hz,1H),7.37–7.31(m,3H),7.22(dd,J＝12.1,5.3Hz,3H),2.90–2.86(m,2H),2.82–2.77(m,2H)；19F NMR(376MHz,CDCl3)δ–112.84––112.92(m,1F),–128.97(s,1F)；13C NMR(100MHz,CDCl3)δ162.7(d,J＝248.3Hz),153.8(d,J＝259.3Hz),148.3(d,J＝5.6Hz),143.1(d,J＝12.9Hz),137.3,135.9(d,J＝3.0Hz),135.8(d,J＝13.0Hz),134.4,131.3(d,J＝8.4Hz),130.8,128.9(d,J＝15.8Hz),128.9,128.3,128.2(d,J＝4.2Hz),127.5,127.2,125.4,115.7115.5,27.9,25.5；HRMS(ESI)calcd for[C25H18F2N(M+H)+]:370.1407,found:m/z 370.1410.
4-(4-chlorophenyl)-3-fluoro-2-phenyl-5,6-dihydrobenzo[h]quinoline(3f):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3f(white solid,169.2mg,88％yield).M.p.:159–160℃；1H NMR(400MHz,CDCl3)δ8.47(dd,J＝7.7,1.1Hz,1H),8.15–8.11(m,2H),7.54–7.49(m,4H),7.46(dt,J＝4.9,2.0Hz,1H),7.41(ddd,J＝8.8,5.5,1.3Hz,1H),7.36–7.30(m,3H),7.23(d,J＝7.4Hz,1H),2.89–2.86(m,2H),2.81–2.76(m,2H)；19F NMR(376MHz,CDCl3)δ–128.96(s,1F)；13C NMR(100MHz,CDCl3)δ153.7(d,J＝259.6Hz),148.4(d,J＝5.8Hz),143.1(d,J＝12.5Hz),137.3,135.8(d,J＝5.6Hz),135.6(d,J＝15.6Hz),134.6,134.4,130.9,130.8(d,J＝1.0Hz),130.7,129.0(d,J＝9.1Hz),128.9(d,J＝6.4Hz),128.8,128.4,127.6,127.2,125.4,27.8,25.4；HRMS(ESI)calcd for[C25H18FClN(M+H)+]:386.1112,found:m/z 386.1111.
4-(4-bromophenyl)-3-fluoro-2-phenyl-5,6-dihydrobenzo[h]quinoline(3g):The crude products were purified by column chromatography with petroleum ether/ethyl acetate(50/1 to 40/1,v/v)as eluent to give compound 3g(white solid,191.5mg,89％yield).M.p.:146–147℃；1H NMR(400MHz,CDCl3)δ8.47(dd,J＝7.7,0.9Hz,1H),8.13(dd,J＝7.0,1.3Hz,2H),7.68–7.64(m,2H),7.54–7.49(m,2H),7.47–7.42(m,1H),7.40(dd,J＝7.6,1.0Hz,1H),7.34(td,J＝7.4,1.4Hz,1H),7.24(t,J＝7.1Hz,3H),2.89–2.86(m,2H),2.81–2.76(m,2H)；19F NMR(376MHz,CDCl3)δ–128.95(s,1F)；13C NMR(100MHz,CDCl3)δ153.6(d,J＝259.5Hz),148.4(d,J＝5.7Hz),143.1(d,J＝12.4Hz),137.3,135.8(d,J＝5.9Hz),135.6(d,J＝15.8Hz),134.4,131.7,131.2,130.6,129.0(d,J＝9.0Hz),128.9(d,J＝6.3Hz),128.4,127.6,127.2,125.4,122.8,27.8,25.4；HRMS(ESI)calcd for[C25H18FBrN(M+H)+]:430.0607,found:m/z 430.0602.
test example 1, results of biological Activity (study of inhibition of growth of human prostate cancer cells in vitro)
Human prostate cancer cell DU145 is used as a detection object, the inhibition of the compound related to the invention on human prostate cancer cell DU145 is evaluated by a cell counting kit method (the specific test method refers to the research that the silkwood essential oil inhibits the in vitro growth of human prostate cancer cells, the 2 nd phase of medical edition of Nantong university, 2020, 113. sup. 116), and the half inhibition rate (50% inhibition concentration, IC) is calculated50). The results are shown in Table 1, and compounds 3b and 3e have significant growth inhibitory effect on human prostate cancer cell DU145, and IC thereof5020.1. mu.M and 19.3. mu.M, respectively.
TABLE 1
Figure BDA0003377986260000101
It should be noted that the above summary and the detailed description are intended to demonstrate the practical application of the technical solutions provided by the present invention, and should not be construed as limiting the scope of the present invention. Various modifications, equivalent substitutions, or improvements may be made by those skilled in the art within the spirit and principles of the invention. The scope of the invention is to be determined by the appended claims.

Claims (9)

1. A3-fluoro-5H-indeno [1,2-b ] pyridine compound is characterized by having the following structural general formula:
Figure FDA0003377986250000011
wherein R is1Independently selected from H, C1～C4Alkyl or halogen;
Ar1is substituted or unsubstituted aryl or heteroaryl, and the substituent on the aryl or heteroaryl is selected from phenyl and C1～C4Alkyl radical, C1～C4One or more of alkoxy and halogen, and the number of carbon atoms of the aryl or heteroaryl is 12 or less;
Ar2is a substituted or unsubstituted aryl group, and the substituent on the aryl group is selected from C1～C4Alkyl radical, C1～C4One or more of alkoxy, phenyl, halogen and hydroxyl, wherein the number of carbon atoms of the aryl is less than or equal to 12.
2. 3-fluoro-5H-indeno [1,2-b ] according to claim 1]Pyridine compound, characterized in that R is1Independently selected from H, methyl or F;
ar is1Is substituted or unsubstituted phenyl or thienyl, and the substituent on the phenyl or the thienyl is selected from one or two of methyl, methoxy, tert-butyl, phenyl, F, Cl and Br;
ar is1Is substituted or unsubstituted phenyl, and the substituent on the phenyl is selected from one or more of methyl, methoxy, phenyl, F, Cl and hydroxyl.
3. The 3-fluoro-5H-indeno [1,2-b ] pyridine compound according to claim 1, wherein the compound is selected from one of the following specific compounds:
Figure FDA0003377986250000021
4. a process for the preparation of 3-fluoro-5H-indeno [1,2-b ] pyridines according to any of claims 1 to 3, comprising the steps of:
under the action of acid, reacting aza-diene compound and difluoroenol silyl ether compound in organic solvent, adding alkali for treatment after the reaction is finished, and separating to obtain the 3-fluoro-5, 6-dihydrobenzo [ h ] quinoline compound;
the structure of the aza-diene compound is shown as the formula (I):
Figure FDA0003377986250000022
the structure of the difluoroenol silyl ether compound is shown as the formula (II):
Figure FDA0003377986250000023
in the formulae (I) and (II), R1、Ar1And Ar2Is as defined in any one of claims 1 to 3.
5. The process of claim 4 wherein the acid is TfOH.
6. The method of claim 4 wherein the organic solvent is 1, 2-dichloroethane.
7. The method for preparing 3-fluoro-5H-indeno [1,2-b ] pyridines according to claim 4, characterized in that the molar ratio of the aza-diene compound, the difluoroenolsilyl ether compound, and the acid is 1: 1.1-1.3: 1.9 to 2.1.
8. The process for preparing 3-fluoro-5H-indeno [1,2-b ] pyridines according to claim 4, characterized in that the reaction temperature is 60-90 ℃ and the reaction time is 4-12 hours.
9. The method of claim 4 wherein the base is selected from the group consisting of ethylenediamine and sodium hydroxide.
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