CN109053618B - Preparation method of oxazole derivative - Google Patents

Preparation method of oxazole derivative Download PDF

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CN109053618B
CN109053618B CN201810748669.7A CN201810748669A CN109053618B CN 109053618 B CN109053618 B CN 109053618B CN 201810748669 A CN201810748669 A CN 201810748669A CN 109053618 B CN109053618 B CN 109053618B
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文丽荣
王加琦
李卫
李明
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Qingdao University of Science and Technology
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    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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Abstract

The invention discloses a preparation method of an oxazole derivative, belonging to the technical field of organic synthesis. The method comprises the following steps: adding substituted p-methylene benzoquinone, substituted N-propargyl amide and indium trichloride into a reactor, adding a solvent 1, 2-dichloroethane, heating until the reaction is finished, concentrating the filtrate by a rotary evaporator to obtain a crude product, and separating by column chromatography to obtain the product. The synthesis method of the oxazole derivative provided by the invention is scientific and reasonable, and has the characteristics of simple synthesis method, high atom economy, easy purification of products and the like. The reaction equation is as follows:

Description

Preparation method of oxazole derivative
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of an oxazole derivative.
Background
Among the various synthetic and naturally occurring heterocyclic structures, the oxazole core is one of the most important simple heterocycles.
Oxazole derivatives are widely present in various natural products and drugs and have remarkable biological activity. Such as antifungal, antiviral, antibacterial, and antiproliferative activity ((a) Chemistry of Heterocyclic Compounds, Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, 2003; Part B,2004.(B) curr. Top. Med. chem.2016,16,3582.(c) Bioorganic Med. chem. Lett.2005,15,5284). Furthermore, oxazoles are also useful synthetic intermediates in organic synthesis and are also important ligands for transition metal catalysis (org. lett.2005,7,2325).
In view of the wide application of oxazole derivatives, the research on the synthesis method of the compounds has important significance.
The conventional preparation method of oxazole derivatives comprises:
1) Robinson-Gabriel synthesis: the 2-acylamino ketone is subjected to intramolecular reaction and dehydration to obtain oxazole, and concentrated sulfuric acid or phosphorus pentoxide and the like are used as dehydrating agents in the reaction.
2) Fischer synthesis: and dissolving equivalent cyanohydrin and aromatic aldehyde in anhydrous ether, and introducing dry hydrogen chloride to obtain the substituted oxazole.
3) Van Leusen Synthesis: refluxing tosylmethylisonitrile (TosMIC, van Leusen reagent) and aldehyde in a protic solvent can give a 5-substituted oxazole. This reaction proceeds mainly due to the specific activity of TosMIC, containing a more acidic proton, a good leaving group (p-toluenesulfonyl) and isonitriles containing an oxidizing carbon atom.
The preparation of oxazole derivatives in the laboratory using the above process has significant disadvantages: 1) equivalent amount of acid or other dehydrating agent is needed; 2) the reaction conditions are harsh; 3) the atom economy is not good.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of an oxazole derivative.
A process for the preparation of an oxazole derivative having the structure of formula i:
Figure GDA0003534047910000021
wherein R is1Selected from phenyl, R2Selected from phenyl, thienyl, naphthyl, p-fluorophenyl, p-methoxyphenyl, and R3Selected from tert-butyl; or R1Is selected from phenyl, and R2Selected from p-methoxyphenyl, R3Selected from phenyl, isopropyl; or R1Selected from thienyl, p-methylphenyl, p-bromophenyl, and R2Selected from p-methoxyphenyl, R3Selected from tert-butyl. It is characterized in that substituted p-methylene benzoquinone and substituted N-propargyl amide with the molar ratio of 1:1.5 are added into a reactor and added into InCl3Under the action, after the heating reaction in the solvent is finished, a rotary evaporator is concentrated to obtain a crude product, and the crude product is separated by silica gel column chromatography to obtain a product, wherein the chemical process is shown as a reaction formula II:
Figure GDA0003534047910000022
the substituted p-methylene benzoquinone, the substituted N-propargyl amide and the InCl3The molar ratio of (A) to (B) is 1:1.5: 0.1. The solvent is selected from 1, 2-dichloroethane, the reaction temperature is 70 ℃, and the reaction time is 1-6 h.
The invention has the beneficial effects that: the synthesis method of the oxazole derivative provided by the invention is scientific and reasonable, and the oxazole derivative with various substituent groups can be synthesized; and has the characteristics of simple synthesis method, high atom economy, easy purification of products and the like.
Drawings
FIG. 1 is an NMR spectrum of Compound 3a prepared in example 1;
FIG. 2 is an NMR spectrum of compound 3f prepared in example 6;
FIG. 3 is an NMR spectrum of compound 3j prepared in example 10.
Detailed Description
The invention is described in further detail below with reference to the following figures and specific examples:
the test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
EXAMPLE 1 preparation of oxazole derivative 3a
Figure GDA0003534047910000031
A25 mL single neck flask was charged with p-methylenequinone 1a (0.5mmol,162.2mg), N-propargylbenzamide 2a (0.75mmol,119.4mg), and InCl3(0.05mmol,11.1 mg). 1, 2-dichloroethane (2.5mL) was added and the mixture was stirred in an oil bath at 70 ℃ to react for 3 hours. After the reaction is finished, cooling to room temperature, removing the solvent by using a rotary evaporator, separating the residue by column chromatography (200-mesh 300-mesh silica gel) (petroleum ether/ethyl acetate: 20/1), washing the solid obtained by rotary evaporation twice by using normal hexane to obtain a white solid oxazole derivative 3a, wherein the yield is highThe content was 94%.
Spectrogram analysis data 3a:
1H NMR(CDCl3,500MHz)δ7.95–7.89(m,2H),7.48–7.37(m,3H),7.03(dd,J＝8.6,8.7Hz,4H),7.05(s,2H),6.63(s,1H),5.08(s,1H,missing after deuteriation),4.28(t,J＝8.0Hz,1H),3.79(s,3H),3.41(d,J＝8.0Hz,2H),1.41(s,18H)；13C NMR(CDCl3,125MHz)δ160.39,158.01,152.19,151.37,136.02,135.68,134.32,129.78,128.65,128.59,127.71,125.91,124.92,124.07,113.79,77.23,76.97,76.72,55.18,49.09,34.31,32.95,30.28,30.26,30.23；HRMS(ESI)m/z calcd for C32H38NO3 +[M+H]+484.2852,found 484.2842.
example 2
2a in example 1 is replaced by 2b, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000041
Spectrogram analysis data 3b:
1H NMR(CDCl3,500MHz)δ7.65(dd,J＝8.5,8.6Hz,4H),7.00(dd,J＝8.6,8.7Hz,4H),7.01(s,2H),6.61(s,1H),5.06(s,1H),4.24(t,J＝8.0Hz,1H),3.77(s,3H),3.38(d,J＝7.9Hz,2H),1.38(s,18H)；13C NMR(CDCl3,125MHz)δ159.52,158.08,152.21,151.77,135.95,135.76,134.24,131.83,128.62,127.38,126.64,125.11,124.13,124.03,113.82,77.20,76.94,76.69,55.17,49.12,34.30,32.92,30.28,30.26,30.23；HRMS(ESI)m/z calcd for C32H37NO3Br+[M+H]+562.1957,found 562.1956.
example 3
2a in example 1 was replaced by 2c, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Figure GDA0003534047910000042
Spectrogram analysis data 3c:
1H NMR(CDCl3,500MHz)δ7.51(dd,J＝8.1,7.9Hz,4H),7.01(dd,J＝8.5,8.5Hz,4H),7.03(s,2H),6.59(s,1H),5.07(s,1H),4.26(t,J＝7.9Hz,1H),3.77(s,3H),3.38(d,J＝7.9Hz,2H),2.39(s,3H),1.39(s,18H)；13C NMR(CDCl3,125MHz)δ160.61,157.99,152.18,151.00,139.97,136.07,135.65,134.36,129.30,128.66,125.87,125.05,124.75,124.07,113.77,77.23,76.97,76.72,55.17,49.06,34.31,32.94,30.25,21.43；HRMS(ESI)m/z calcd for C33H40NO3 +[M+H]+498.3008,found 498.3001.
example 4
2a in example 1 is replaced by 2d, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000051
Spectrogram analysis data 3d:
1H NMR(CDCl3,500MHz)δ7.54(d,J＝2.7Hz,1H),7.36(d,J＝4.8Hz,1H),7.01(dd,J＝8.5,8.6Hz,4H),7.10–7.04(m,1H),7.02(s,2H),6.54(s,1H),5.06(s,1H),4.25(t,J＝7.9Hz,1H),3.77(s,3H),3.37(d,J＝7.9Hz,2H),1.39(s,18H)；13C NMR(CDCl3,125MHz)δ158.01,156.60,152.20,150.94,135.92,135.68,134.24,130.37,128.65,127.71,127.50,126.84,124.82,124.03,113.79,77.23,76.98,76.72,55.18,48.93,34.31,32.86,30.26；HRMS(ESI)m/z calcd for C30H36NO3S+[M+H]+490.2416,found 490.2412.
example 5
1a in example 1 is replaced by 1e, other conditions are the same as in example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000052
Spectrogram analysis data 3e:
1H NMR(CDCl3,500MHz)δ7.95–7.86(m,2H),7.45–7.37(m,3H),7.25–7.19(m,2H),7.01(s,2H),7.00–6.93(m,2H),6.63(s,1H),5.09(s,1H),4.30(t,J＝7.9Hz,1H),3.40(d,J＝7.9Hz,2H),1.39(s,18H)；13C NMR(CDCl3,125MHz)δ165.83,162.38,160.52,152.35,150.98,139.90,139.54,135.82,133.79,129.88,129.19,129.13,128.63,127.61,125.91,125.02,124.04,115.26,115.10,77.22,76.97,76.71,49.14,34.32,32.82,30.23；HRMS(ESI)m/z calcd for C31H35NO2F+[M+H]+472.2652,found 472.2648.
example 6
1f is used instead of 1a in example 1, the conditions are the same as in example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000061
Spectrogram analysis data 3f:
1H NMR(CDCl3,500MHz)δ7.95–7.86(m,2H),7.46–7.36(m,3H),7.33–7.27(m,4H),7.23–7.18(m,1H),7.05(s,2H),6.63(s,1H),5.08(s,1H),4.31(t,J＝7.9Hz,1H),3.52–3.36(m,2H),1.39(s,18H)；13C NMR(CDCl3,125MHz)δ160.43,152.27,151.26,143.86,135.71,133.96,129.80,128.59,128.42,127.72,127.69,126.34,125.91,124.95,124.16,77.23,76.97,76.72,49.93,34.32,32.72,30.27,30.25,30.22；HRMS(ESI)m/z calcd for C31H36NO2 +[M+H]+454.2746,found 454.2737.
example 7
1a in example 1 was replaced by 1g, and the experimental results are shown in Table 1, except that the conditions were the same as in example 1.
Figure GDA0003534047910000071
3g of spectrogram analysis data:
1H NMR(CDCl3,500MHz)δ7.94–7.86(m,2H),7.44–7.37(m,3H),7.15(d,J＝5.1Hz,1H),7.08(s,2H),6.93–6.88(m,1H),6.84(d,J＝3.4Hz,1H),6.67(s,1H),5.11(s,1H),4.53(t,J＝7.8Hz,1H),3.52–3.33(m,2H),1.38(s,18H)；13C NMR(CDCl3,125MHz)δ160.56,152.61,150.65,148.04,135.79,133.50,129.88,128.63,127.62,126.54,125.95,125.22,124.26,124.07,123.72,77.26,77.01,76.75,45.80,34.56,34.33,30.25；HRMS(ESI)m/z calcd for C29H34NO2S+[M+H]+460.2310,found 460.2305.
example 8
1a in example 1 is replaced by 1h, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000072
Spectrogram analysis data 3h:
1H NMR(CDCl3,500MHz)δ7.90–7.85(m,2H),7.81–7.76(m,3H),7.74(s,1H),7.47–7.38(m,6H),7.10(s,2H),6.65(s,1H),5.09(s,1H),4.49(t,J＝7.9Hz,1H),3.60–3.48(m,2H),1.39(s,18H)；13C NMR(CDCl3,125MHz)δ160.49,152.36,151.21,141.37,135.80,133.85,133.47,132.24,129.81,128.60,128.09,127.76,127.67,127.53,126.41,125.99,125.93,125.46,125.03,124.28,77.25,77.00,76.74,50.01,34.34,32.60,30.27；HRMS(ESI)m/z calcd for C35H38NO2 +[M+H]+504.2903,found 504.2902.
example 9
1a in example 1 is replaced by 1i, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000081
Spectrogram analysis data 3i:
1H NMR(CDCl3,500MHz)δ7.96–7.86(m,2H),7.46–7.35(m,3H),6.99(dd,J＝8.5,8.5Hz,4H),6.90(s,2H),6.60(s,1H),4.84(s,1H),4.29(t,J＝7.9Hz,1H),3.76(s,3H),3.39(d,J＝7.9Hz,2H),3.16–3.02(m,2H),1.24–1.14(m,12H)；13C NMR(CDCl3,125MHz)δ160.40,157.97,151.28,148.49,136.05,135.47,133.59,129.82,128.60,127.66,125.92,124.94,122.60,113.78,77.24,76.99,76.74,55.19,48.75,32.84,27.25,22.72；HRMS(ESI)m/z calcd for C30H34NO3 +[M+H]+456.2539,found 456.2534.
example 10
1j is used for replacing 1a in example 1, other conditions are the same as example 1, and the experimental results are shown in Table 1.
Figure GDA0003534047910000082
Spectrogram analysis data 3j:
1H NMR(CDCl3,500MHz)δ7.98–7.89(m,2H),7.51–7.48(m,3H),7.48–7.30(m,10H),7.03(dd,J＝8.5,8.5Hz,4H),7.16(s,2H),6.68(s,1H),5.38(s,1H),4.39(t,J＝7.9Hz,1H),3.77(s,3H),3.54–3.39(m,2H)；13C NMR(CDCl3,125MHz)δ160.58,158.17,150.99,147.86,137.56,135.91,135.64,131.39,129.94,129.30,129.10,128.77,128.67,128.58,128.23,127.60,125.97,125.07,113.97,77.26,77.00,76.75,55.21,48.36,32.51；HRMS(ESI)m/z calcd for C36H30NO2 +[M+H]+524.2226,found 524.2225。
TABLE 1
Figure GDA0003534047910000091

Claims (2)

1. A process for the preparation of an oxazole derivative having the structure of formula i:
Figure FDA0003534047900000011
wherein R is1Selected from phenyl, R2Selected from phenyl, thienyl, naphthyl, p-fluorophenyl, p-methoxyphenyl, and R3Selected from tert-butyl; or R1Is selected from phenyl, and R2Selected from p-methoxyphenyl, R3Selected from phenyl, isopropyl; or R1Selected from thienyl, p-methylphenyl, p-bromophenyl, and R2Selected from p-methoxyphenyl, R3Selected from tert-butyl. It is characterized in that substituted p-methylene benzoquinone and substituted N-propargyl amide are added into a reactor in InCl3Catalytically, heating at 70 deg.C for 1-6 hr in 1, 2-Dichloroethane (DCE) solvent. After the reaction is finished, concentrating by a rotary evaporator to obtain a crude product, and separating by column chromatography silica gel to obtain an oxazole derivative shown in a formula I; the preparation method is expressed by the following equation:
Figure FDA0003534047900000012
2. the method of claim 1, wherein: substituted p-methylenebenzoquinone, substituted N-propargylamides and InCl3The molar ratio of (A) to (B) is 1:1.5: 0.1.
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