CN115260136B - Phthalide compound and preparation method thereof - Google Patents
Phthalide compound and preparation method thereof Download PDFInfo
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- CN115260136B CN115260136B CN202210950641.8A CN202210950641A CN115260136B CN 115260136 B CN115260136 B CN 115260136B CN 202210950641 A CN202210950641 A CN 202210950641A CN 115260136 B CN115260136 B CN 115260136B
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
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Abstract
The invention provides a phthalide compound and a preparation method thereof, wherein the phthalide compound has a structure shown in a formula I:wherein R1 is-H, halogen group, methoxy or methyl; r2 is aryl, alkyl or hydrogen. Mixing N-methoxy benzamide, a catalyst and an organic solvent for synthesis reaction, wherein the temperature of the synthesis reaction is 70-80 ℃, the synthesis reaction time is 10-12 hours, and the phthalide compound is obtained; n-methoxy benzamide is used as a raw material to synthesize the phthalide compound in one step, and the method is simple and rapid and has wide substrate applicability.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a phthalide compound and a preparation method thereof.
Background
Phthalides are an important class of heterocyclic compounds which exist in nature, and many drugs or drug intermediates contain phthalide units. More and more studies have shown that: the phthalide derivatives have pharmacological activities such as antipyresis, pain relieving, anti-tumor, antibacterial and antifungal activities. Such as: pomalidomide (Pomalyst) has excellent antitumor activity.
In 2020, group Yu Jinquan reported the synthesis of phthalides (bond-EnabledPd (II) -Catalyzed C (sp 3) -H Lactonization Using Molecular Oxygen as oxidant. Org. Lett.2020,22, 3960-3963) using Pd Catalyzed reactions starting with o-methylbenzoic acid. The reaction is efficient, but the cost of the synthetic catalyst of the raw materials is high, the reaction condition is high, the reaction time is long, the phthalide compound and the preparation method thereof are particularly developed based on the factors, and compared with the traditional noble metal method, the method has the advantages of cost advantage, short reaction time, simplicity, high efficiency and mild reaction condition.
Disclosure of Invention
The invention aims to provide a phthalide compound and a preparation method thereof, and the preparation method has cost advantages compared with the traditional noble metal method.
The invention aims at realizing the following technical scheme: a phthalide compound having a structure represented by formula I:
wherein R1 is-H, halogen group, methoxy or methyl; r2 is aryl, alkyl or hydrogen.
Further, the halogen group includes-F, -Cl or-Br.
Further, the preparation method of the phthalide compound comprises the following steps:
mixing N-benzamide, a catalyst and methanol with an organic solvent, and carrying out a synthesis reaction at 70-80 ℃ for 10-12 hours to obtain a phthalide compound;
the N-methoxy benzamide has a structure shown in a formula II;
the N-benzamide preferably comprises one of N-methoxybenzamide, N- (4-methoxyphenyl) benzamide and N-pivaloyloxy benzamide.
Further, specifically: adding N-methoxy-2 ethyl-benzamide, ferrous chloride and methanol into 1,4 dioxane, mixing, heating the obtained reaction solution to 70 ℃ under the condition of nitrogen and illumination, carrying out synthetic reaction for 12 hours, filtering the obtained reaction solution, and separating the obtained filtrate by column chromatography to obtain 3-methyl isobenzofuran-1 (3H) -ketone, wherein the separation yield is 80%, and the synthetic reaction equation is as follows:
further, specifically: adding N-methoxy-2 methyl-benzamide, ferrous chloride and methanol into 1,4 dioxane, mixing, heating the obtained reaction solution to 70 ℃ under the condition of nitrogen and illumination, carrying out synthetic reaction for 10 hours, filtering the obtained reaction solution, and separating the obtained filtrate by column chromatography to obtain isobenzofuran-1 (3H) -ketone, wherein the separation yield is 75%, and the synthetic reaction equation is as follows:
further, the molar ratio of the N-methoxybenzamide to the catalyst is 1:0.2-0.4.
Further, the catalyst is ferrous chloride or ferric chloride; the mole percentage of the catalyst is 20-40%.
Further, the organic solvent includes 1, 2-dichloroethane, 1, 4-dioxane or tetrahydrofuran.
Compared with the prior art, the invention has the beneficial effects that:
the invention provides a preparation method of phthalide compounds, which does not use noble metal, has simple reaction conditions, mild reaction conditions and shorter reaction time.
The method takes the simple and easily obtained N-methoxy benzamide as the raw material to synthesize the phthalide compound in one step, and has the advantages of simplicity, rapidness and wide substrate applicability.
Drawings
FIG. 1 is a schematic diagram of the structure of a 4-phthalide compound;
FIG. 2 is a synthetic reaction equation.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments, and all other embodiments obtained by those skilled in the art without making creative efforts based on the embodiments of the present invention are included in the protection scope of the present invention.
The invention is further described with reference to FIGS. 1-2, which provide a phthalide compound having a structure represented by formula I:
wherein R1 is-H, halogen group, methoxy or methyl; r2 is aryl, alkyl or hydrogen. In the present invention, the halogen group preferably includes-F, -Cl or-Br; in the present invention,
the aryl is preferably phenyl, and the alkyl is preferably methyl or ethyl.
The invention provides a synthesis method of phthalide compounds, which comprises the following steps:
mixing N-methoxy benzamide, a catalyst, additional methanol and an organic solvent, and carrying out a synthesis reaction under illumination to obtain a phthalide compound;
the N-methoxy benzamide has a structure shown in a formula II;
in the present invention, the N-benzamide preferably includes N-methoxybenzamide, N- (4-methoxyphenyl) benzamide, N-pivaloyloxy-benzamide.
In the present invention, the catalyst is preferably ferrous chloride, ferric chloride;
the molar percentage of the N-methoxybenzamide to the catalyst is preferably 20-40%, more preferably 30-40%.
In the present invention, the organic solvent preferably includes 1, 2-dichloroethane, 1,4 dioxane or tetrahydrofuran.
The mixing process is not particularly limited, and mixing processes well known to those skilled in the art may be used.
In the invention, the temperature of the synthesis reaction is 70-80 ℃, and the time of the synthesis reaction is 10-12h. After the synthesis reaction is completed, the reaction liquid is preferably filtered, and then the obtained filtrate is subjected to column chromatography separation to obtain the phthalide compound.
The specific mode and conditions of the filtration and column chromatography separation are not particularly limited, and modes and conditions well known to those skilled in the art can be selected.
The phthalides and the preparation method thereof provided by the invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the invention.
Example 1
N-methoxy-2 methyl-benzamide (1 a, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resulting reaction solution was heated to 70℃under nitrogen and light conditions, the synthesis reaction was carried out for 10 hours, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to give isobenzofuran-1 (3H) -one (4 a). The isolation yield was 75%; the synthetic reaction equation for example 1 is as follows:
1H NMR(400MHz,CDCl3)δ7.91–7.89(m,1H),7.69–7.65(m,1H),7.54–7.48(m,2H),5.31(s,2H).13C{1H}NMR(100MHz,CDCl3)δ170.7,146.5,134.0,125.7,125.7,122.0,69.7；HRMS(ESI-TOF):([M+H]+)calcd for C8H7O2+:135.0446；found:135.0445。
example 2
N-methoxy-2 ethyl-benzamide (1 b, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resulting reaction solution was heated to 70℃under nitrogen and light conditions, the synthesis reaction was carried out for 10 hours, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to obtain 3-methyl isobenzofuran-1 (3H) -one (4 b). The separation yield is 80%; the synthetic reaction equation for example 2 is as follows:
1H NMR(400MHz,CDCl3)δ7.77–7.75(m,1H),7.62–7.58(m,1H),7.45–7.38(m,2H),5.49(q,J＝6.3Hz,1H),1.54(d,J＝6.7Hz,3H).13C{1H}NMR(100MHz,CDCl3)δ170.5,151.2,134.1,129.0,125.5,125.4,121.7,77.8,20.3；IR(NaCl)；HRMS(ESI-TOF):([M+H]+)calcdforC10H11O2+:149.0603；found:149.0609。
example 3
2-benzyl-N-methoxybenzamide (1 c, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resulting reaction solution was heated to 70℃under nitrogen and light conditions, the synthesis reaction was carried out for 10 hours, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to give 3-phenylisobenzofuran-1 (3H) -one (4 a). The isolation yield was 68%; the synthetic reaction equation for example 3 is as follows:
1H NMR(400MHz,CDCl3)δ7.99–7.94(m,1H),7.66–7.62(m,1H),7.58–7.53(m,1H),7.42–7.23(m,7H),6.40(s,1H)；13C{1H}NMR(100MHz,CDCl3)δ170.6,149.7,136.4,134.3,129.4,129.3,129.0,127.0,125.7,125.56,122.9,82.7；HRMS(ESI-TOF):([M+H]+)calcd for C14H11O2+:211.0759；found:211.0756。
example 4
2-ethyl-N, 5-dimethoxy benzamide (1 d, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resultant reaction solution was heated to 70℃under nitrogen and light conditions, the synthesis reaction was carried out for 10 hours, the resultant reaction solution was filtered, and the resultant filtrate was separated by column chromatography to obtain 6-methoxy-3 methyl isobenzofuran-1 (3H) -one (4 d). The isolation yield was 61%; the synthetic reaction equation for example 4 is as follows:
1H NMR(400MHz,CDCl3)δ7.30–7.25(m,2H),7.21–7.19(m,1H),5.49(q,J＝6.6Hz,1H),3.83(s,3H),1.57(d,J＝6.6Hz,3H).13C{1H}NMR(100MHz,CDCl3)δ170.7,170.5,160.6,143.7,123.0,122.4,107.4,77.7,55.8,20.5；HRMS(ESI-TOF):([M+H]+)calcd for C10H11O3+:179.0708；found:179.0713。
example 5
5-chloro-2-ethyl-N-methoxybenzamide (1 e, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resulting reaction solution was heated to 70℃under nitrogen and light conditions for a synthetic reaction for 10 hours, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to give 6-chloro-3-methylisobenzofuran-1 (3H) -one (4 e). The isolation yield was 61%; the synthetic reaction equation for example 5 is as follows:
1H NMR(400MHz,CDCl3)δ7.82(s,1H),7.62–7.60(m,1H),7.37–7.35(m,1H),5.53(q,J＝6.6Hz,6.1Hz,1H),1.60(d,J＝5.8Hz,3H).13C{1H}NMR(100MHz,CDCl3)δ168.9,149.3,135.4,134.3,127.6,125.6,122.9,77.6,20.3；HRMS(ESI-TOF):([M+H]+)calcd for C9H8ClO2+:183.0213；found:183.0218。
example 6
2-methyl-N, 4, 5-trimethoxybenzamide (1 f, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resultant reaction solution was heated to 70℃under nitrogen and light conditions for synthesis reaction for 10 hours, the resultant reaction solution was filtered, and the resultant filtrate was separated by column chromatography to give 5, 6-dimethoxy isobenzofuran-1 (3H) -one (4 f). The isolation yield was 61%; the synthetic reaction equation for example 6 is as follows:
1H NMR(400MHz,CDCl3)δ7.29(s,1H),6.89(s,1H),5.20(s,2H),3.96(s,3H),3.92(s,3H).13C{1H}NMR(100MHz,CDCl3)δ171.5,154.9,150.4,141.0,117.6,106.1,103.4,69.1,56.4,56.3；HRMS(ESI-TOF):([M+H]+)calcdforC10H11O4+:195.0657；found:195.0665。
example 7
5-bromo-N-methoxy-2-methylbenzamide (1 g, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resultant reaction solution was heated to 70℃under nitrogen and light conditions to conduct a synthetic reaction for 10 hours, the resultant reaction solution was filtered, and the resultant filtrate was separated by column chromatography to give 6-bromoisobenzofuran-1 (3H) -one (4 g). The isolation yield was 61%; the synthetic reaction equation for example 7 is as follows:
1H NMR(400MHz,CDCl3)δ8.03(s,1H),7.79(d,J＝8.0Hz,1H),7.38(d,J＝8.0Hz,1H),5.27(s,2H).13C{1H}NMR(100MHz,CDCl3)δ169.5,145.1,137.1,128.8,127.8,123.7,123.0,69.5；HRMS(ESI-TOF):([M+H]+)calcd for C8H6BrO2+:212.9551；found:212.9557。
example 8
N-methoxy-2-pentylbenzamide (1H, 0.10M), ferrous chloride (40 mol%) and methanol (1 eq, 0.10M) were added to 1,4 dioxane and mixed, the resulting reaction solution was heated to 70℃under nitrogen and light conditions, the synthesis reaction was carried out for 10H, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to give 3-butylbenzofuran-1 (3H) -one (4H). The isolation yield was 61%; the synthetic reaction equation for example 8 is as follows:
1H NMR(400MHz,CDCl3)δ7.92–7.83(m,1H),7.70–7.62(m,1H),7.54–7.47(m,1H),7.45–7.40(m,1H),5.46(dd,J＝7.0,3.5Hz,1H),2.06–1.99(m,1H),1.79–1.70(m,1H),1.48–132(m,4H),0.89(t,J＝6.1Hz,3H).13C{1H}NMR(100MHz,CDCl3)δ170.7,150.1,133.9,129.0,126.1,125.6,121.7,81.4,34.4,26.9,22.4,13.9；HRMS(ESI-TOF):([M+H]+)calcd for C10H11O2+:191.1072；found:191.1066。
as can be seen from the above examples, the present invention provides a phthalide compound and a preparation method thereof, wherein noble metals are not used in the method, the reaction time is shorter, and the reaction conditions are mild; the method takes the simple and easily available N-methoxy benzamide as the raw material to synthesize the phthalide compound in one step, and has the advantages of simplicity, rapidness and wide substrate applicability.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (4)
1. The preparation method of the phthalide compound is characterized by comprising the following steps:
mixing N-methoxy benzamide, a catalyst and methanol with an organic solvent, and carrying out a synthesis reaction at 70-80 ℃ for 10-12 hours to obtain a phthalide compound; the catalyst is ferrous chloride or ferric chloride, and the molar ratio of the N-methoxy benzamide to the catalyst is 1:0.2-0.4;
the N-methoxy benzamide has a structure shown in a formula I I;
wherein R1 is-H, halogen group, methoxy or methyl; r2 is aryl, alkyl or hydrogen.
2. The preparation method of the phthalide compound according to claim 1, which is characterized by comprising the following steps: adding N-methoxy-2 ethyl-benzamide, ferrous chloride and methanol into 1,4 dioxane, mixing, heating the obtained reaction solution to 70 ℃ under the condition of nitrogen and illumination, carrying out synthetic reaction for 12 hours, filtering the obtained reaction solution, and separating the obtained filtrate by column chromatography to obtain 3-methyl isobenzofuran-1 (3H) -ketone, wherein the separation yield is 80%, and the synthetic reaction equation is as follows:
3. the preparation method of the phthalide compound according to claim 1, which is characterized by comprising the following steps: adding N-methoxy-2 methyl-benzamide, ferrous chloride and methanol into 1,4 dioxane, mixing, heating the obtained reaction solution to 70 ℃ under the condition of nitrogen and illumination, carrying out synthetic reaction for 10 hours, filtering the obtained reaction solution, and separating the obtained filtrate by column chromatography to obtain isobenzofuran-1 (3H) -ketone, wherein the separation yield is 75%, and the synthetic reaction equation is as follows:
4. the method for preparing phthalide compound according to claim 1, wherein the organic solvent comprises 1, 2-dichloroethane, 1, 4-dioxane or tetrahydrofuran.
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| CN1333764A (en) * | 1998-12-04 | 2002-01-30 | 武田药品工业株式会社 | Benzofuran derivatives, process for the preparation of the same and uses thereof |
| JP2002161088A (en) * | 1998-12-04 | 2002-06-04 | Takeda Chem Ind Ltd | Benzofuran derivative, method for producing the same and application thereof |
| CN103965147A (en) * | 2009-03-10 | 2014-08-06 | 武田药品工业株式会社 | Benzofuran derivatives |
| CN104829565A (en) * | 2015-05-11 | 2015-08-12 | 华东师范大学 | Furanone derivative and synthetic method thereof |
| CN108912076A (en) * | 2018-08-31 | 2018-11-30 | 信阳师范学院 | A kind of synthetic method of benzo oxygen helerocyclics |
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| WO2013072830A1 (en) * | 2011-11-18 | 2013-05-23 | Council Of Scientific & Industrial Research | A single step enantioselective process for the preparation of 3-substituted chiral phthalides |
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| CN1333764A (en) * | 1998-12-04 | 2002-01-30 | 武田药品工业株式会社 | Benzofuran derivatives, process for the preparation of the same and uses thereof |
| JP2002161088A (en) * | 1998-12-04 | 2002-06-04 | Takeda Chem Ind Ltd | Benzofuran derivative, method for producing the same and application thereof |
| CN103965147A (en) * | 2009-03-10 | 2014-08-06 | 武田药品工业株式会社 | Benzofuran derivatives |
| CN104829565A (en) * | 2015-05-11 | 2015-08-12 | 华东师范大学 | Furanone derivative and synthetic method thereof |
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