CN110294719B - Synthesis method of thiazolidone compound - Google Patents

Synthesis method of thiazolidone compound Download PDF

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CN110294719B
CN110294719B CN201910634289.5A CN201910634289A CN110294719B CN 110294719 B CN110294719 B CN 110294719B CN 201910634289 A CN201910634289 A CN 201910634289A CN 110294719 B CN110294719 B CN 110294719B
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李滨
林桥
林子睿
张诗玲
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Yueyang Wanmu New Material Technology Co ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

The invention relates to a synthesis method of thiazolidone compounds, which comprises the step of synthesizing the thiazolidone compounds by reacting benzyl halide compounds and 2- (methylthio) -4,5-dihydrothiazole in a solvent under the catalysis condition of an alkali reagent and iodine through a one-pot method under the heating condition. The synthesis method has the advantages of simple and easily obtained starting materials, high product yield and simple and convenient operation, and the intermediate product is the 2-oxazolidinethione except the final product and is extremely easy to be converted into the final product thiazolidinone, so that the intermediate separation is not needed. The invention uses less raw materials, has low price, can reduce the investment of capital and labor force, and provides a simple and efficient preparation method for thiazolidone compounds. The invention has good practical value and social and economic efficiency, and has good reference significance for the process development of similar products and downstream products.

Description

Synthesis method of thiazolidone compound
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of thiazolidone compounds.
Background
Thiazolidinone structures are present in many natural products and play an important role in medicine as well as in modern organic synthetic chemistry. Thiazolidone compounds represent a class of well-known patent drugs and substances in different research stages, have the activities of reducing blood sugar, resisting inflammation, benefiting gallbladder, resisting tumors, promoting urination, stimulating immunity and the like, and also have the effects of killing bacteria, killing insects, resisting thyroid diseases and the like, so that the thiazolidone compounds are widely concerned. In the prior art, the mainstream thiazolidinone synthesis methods comprise the following steps: the simplest early synthesis was by cyclization of aminothiols with carbonyl-providing compounds or by direct reaction of aminoethanol with carbonyl sulfide catalyzed by montmorillonite or pyridine, etc. (Tetrahedron lett.1975,16,1969 syn. Comm.1987,17, 1577. Among such methods, aminothiols are on the market and are on the market, limiting the application of the method to a certain extent. In addition, the synthesis of products by reflux reaction of cyclic ketones, thioglycolic acid and ammonium carbonate in benzene has also been reported (org. Prep. Proc. Int.1992,24,81). This method, which contains a mercapto group-containing raw material, generally gives off an unpleasant odor and has the drawback of low yield. Also obtained by transition metal catalysis (J.org.chem.2018, 83,1059, angew.chem.int.ed.2015,54,10944 ACS chem.Neurosci.2016,7, 897), but the ruthenium metal complex in the current synthetic method is expensive, and the post-treatment is too complicated to influence the industrial efficiency. Therefore, it is highly desirable to find a synthesis method of thiazolidinone compounds with a better synthetic route.
Disclosure of Invention
The invention aims to overcome the defects of the prior preparation technology and provide a synthetic method of thiazolidone compounds, which has the advantages of simple and easily obtained starting materials, high product yield and simple and convenient operation.
The technical scheme of the invention is as follows: a synthesis method of thiazolidone compounds is disclosed, wherein benzyl halide compounds and 2- (alkylthio) -4,5-dihydrothiazole are used as reaction raw materials, an alkali reagent and iodine are used as catalysts, and the thiazolidone compounds are obtained by a one-pot reaction in a solvent under the heating condition, and the reaction formula is shown as follows:
Figure BDA0002129711350000011
wherein in the benzyl halide compound, R has the following general formula:
Figure BDA0002129711350000021
wherein R is 0 Is alkyl with 1-22 carbon atoms, and when the number of the carbon atoms is more than 3, the alkyl structure is selected from straight chain, branched chain or cyclic alkyl chain.
R 1 -R 5 The substituent group is independently selected from hydrogen atom, halogen, alkenyl, alkynyl, aryl, hydroxyl, amino, carbonyl, amino, carboxyl, ester group, cyano, phenyl, benzyl, nitro or alkyl with 1-22 carbon atoms, and when the number of the carbon atoms is more than 3, the alkyl structure is selected from straight chain, branched chain or cyclic alkyl chain.
X is selected from halogen.
Further, X is selected from bromine atoms.
Further, the synthesis method of the thiazolidone compound comprises the step of selecting the alkali reagent from one or more of potassium carbonate, potassium hydroxide, potassium acetate, potassium bicarbonate and potassium tert-butoxide.
Further, the synthesis method of the thiazolidone compound is characterized in that the alkali reagent is potassium tert-butoxide.
Further, the synthesis method of the thiazolidinone compound is characterized in that the solvent is selected from one of dimethyl carbonate, toluene, carbon tetrachloride, ethanol, tetrahydrofuran, acetonitrile and water.
Further, the synthesis method of the thiazolidinone compound is characterized in that the solvent is dimethyl carbonate.
Further, the synthesis method of the thiazolidinone compound, wherein the heating temperature is 30-120 ℃, and the reaction time is 10-24 hours.
Further, the synthesis method of the thiazolidinone compound, wherein the heating temperature is 80-100 ℃, and the reaction time is 16-20 hours.
Further, the synthesis method of the thiazolidone compound is characterized in that the molar ratio of the benzyl halide compound, the 2- (alkylthio) -4,5-dihydrothiazole, the alkali agent and the iodine is 1:0.5:0.5:1.
further, a method for synthesizing the thiazolidinone compound, the compound R 0 Is selected from methyl.
Further, a synthesis method of the thiazolidinone compound, wherein R 1 -R 5 At least 4 of which are selected from hydrogen atoms.
The invention has the following beneficial effects:
the thiazolidone compound can be obtained by using cheap benzyl halide and 2- (alkylthio) -4,5-dihydrothiazole as reaction raw materials, using an alkali reagent and iodine as catalysts and performing one-pot reaction in a solvent under the heating condition. The synthesis method has the advantages of simple preparation of the initial raw materials, convenient operation and higher yield of the final product; the intermediate in the conversion process, other than the final product, is a 2-oxazolidinethione, which is very easily converted to the final product thiazolidinone, so no intermediate isolation is required. The invention has the advantages of less raw material amount and low price, can reduce the investment of capital and labor force, and provides a simple and efficient preparation method for thiazolidone compounds. The invention has good practical value and social and economic efficiency, and has good reference significance for the process development of similar products and downstream products.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of 3-benzylthiazolidin-2-one in example 1-1 to example 1-3.
FIG. 2 is a nuclear magnetic resonance carbon spectrum of 3-benzylthiazolidin-2-one in example 1-1 to example 1-3.
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of 3- (2-methylbenzyl) thiazolidin-2-one in example 2-1 to example 2-3.
FIG. 4 is a nuclear magnetic resonance carbon spectrum of 3- (2-methylbenzyl) thiazolidin-2-one in example 2-1 to example 2-3.
FIG. 5 is a NMR chart of 3- (4-methylbenzyl) thiazolidin-2-one in example 3.
FIG. 6 is a NMR carbon spectrum of 3- (4-methylbenzyl) thiazolidin-2-one in example 3.
FIG. 7 is a NMR spectrum of 3- (4- (tert-butyl) benzyl) thiazolidin-2-one in example 4.
FIG. 8 is a NMR carbon spectrum of 3- (4- (tert-butyl) benzyl) thiazolidin-2-one in example 4.
FIG. 9 is a NMR chart of 3- (4-bromobenzyl) thiazolidin-2-one in example 5.
FIG. 10 is a NMR spectrum of 3- (4-bromobenzyl) thiazolidin-2-one in example 5.
FIG. 11 shows a general formula of a chemical equation for synthesizing thiazolidinone compounds.
Detailed Description
Hereinafter, the synthesis of thiazolidinone compounds according to the invention will be further illustrated by reference to the following examples. The scope of the invention is not limited to the embodiments.
Example 1-1: synthesis method (1) of 3-benzylthiazolidine-2-one
Figure BDA0002129711350000031
Benzyl bromide (119. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium hydroxide (23mg, 0.5 mmol), iodine (256 mg, 1.0mmol) and dimethyl carbonate (1 ml) were sequentially added to a reaction tube, and the reaction was electromagnetically stirred at a reaction temperature of 80 ℃ for 16 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to give a pale yellow liquid (73mg, 76%).
Examples 1 to 2: synthesis method (2) of 3-benzylthiazolidine-2-one
Figure BDA0002129711350000041
Benzyl bromide (119. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium carbonate (69mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and dimethyl carbonate (1 ml) were added in this order to a reaction tube, and the reaction was carried out with electromagnetic stirring at a reaction temperature of 80 ℃ for 16 hours. After the reaction was complete, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to yield a pale yellow liquid (80mg, 83%).
Examples 1 to 3: synthesis method (3) of 3-benzylthiazolidine-2-one
Figure BDA0002129711350000042
Benzyl bromide (119. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and dimethyl carbonate (1 ml) were added to a reaction tube in this order, and the reaction was magnetically stirred at a reaction temperature of 100 ℃ for 16 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to yield a pale yellow liquid (83mg, 86%).
Product characterization data were as follows:
1 H NMR(400MHz,CDCl 3 ):δ＝7.37-7.26(m,5H),4.48(s,2H),3.51(t,2H,J＝7.2Hz),3.22(t,2H,J＝7.2Hz)。
13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ＝172.2,136.0,128.8,128.1,127.9,48.6,48.0,25.5.HRMS(EI):C 10 H 12 ONS[M+H] + theoretical value of m/z: 194.0634, found: 194.0639.
example 2-1: method for synthesizing 3- (2-methylbenzyl) thiazolidine-2-ketone (1)
Figure BDA0002129711350000043
O-methylbenzyl bromide (134. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.05mmol), iodine (256 mg,1.0 mmol) and dimethyl carbonate (1 ml) were added in this order to a reaction tube, and reaction was carried out by electromagnetic stirring at a reaction temperature of 80 ℃ for 24 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to give a pale yellow liquid (89mg, 86%) after separation.
Example 2-2: method for synthesizing 3- (2-methylbenzyl) thiazolidine-2-ketone (2)
Figure BDA0002129711350000051
O-methylbenzyl bromide (134. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and dimethyl carbonate (1 ml) were added in this order to a reaction tube, and the reaction was carried out with electromagnetic stirring at a reaction temperature of 50 ℃ for 24 hours. After the reaction was complete, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to yield a pale yellow liquid (70mg, 68%).
Examples 2 to 3: method for synthesizing 3- (2-methylbenzyl) thiazolidine-2-ketone (3)
Figure BDA0002129711350000052
O-methylbenzyl bromide (134. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and dimethyl carbonate (1 ml) were added in this order to a reaction tube, and the reaction was carried out with electromagnetic stirring at a reaction temperature of 100 ℃ for 24 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to give a pale yellow liquid (86mg, 85%) after separation.
The product detection data were as follows:
1 H NMR(600MHz,CDCl 3 ):δ＝7.22-7.17(m,4H),4.49(s,2H),3.44(t,2H,J＝7.2Hz),3.21(t,2H,J＝7.2Hz),2.31(s,3H)。
13 C{ 1 H}NMR(150MHz,CDCl 3 ):δ＝171.9,136.9,133.9,130.8,129.0,128.1,126.3,48.0,46.9,25.6,19.2.HRMS(EI):C 11 H 14 ONS[M+H] + theoretical value of m/z: 208.0791, found: 208.0792.
example 3: synthetic method of 3- (4-methylbenzyl) thiazolidine-2-ketone
Figure BDA0002129711350000061
P-methylbenzyl bromide (185mg, 1mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and toluene (1 ml) were added to a reaction tube in this order, and the reaction was stirred magnetically at a reaction temperature of 80 ℃ for 16 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to yield a pale yellow liquid (1699 mg, 82%).
The product detection data were as follows:
1 H NMR(400MHz,CDCl 3 ):δ＝7.28-7.17(m,4H),4.45(s,2H),3.51(t,2H,J＝7.2Hz),3.22(t,2H,J＝7.6Hz),2.36(s,3H)。
13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ＝172.2,137.7,133.0,129.5,128.3,128.2,48.5,48.0,25.6,21.2.HRMS(EI):C 11 H 14 ONS[M+H] + theoretical value of m/z: 208.0791, found: 208.0796.
example 4: synthetic method of 3- (4- (tert-butyl) benzyl) thiazolidine-2-ketone
Figure BDA0002129711350000062
P-tert-butylbenzylbromide (185. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and tetrahydrofuran (1 ml) were added to a reaction tube in this order, and the reaction was carried out with electromagnetic stirring at a reaction temperature of 80 ℃ for 20 hours. After completion of the reaction, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to give a colorless solid (112mg, 90%).
The product detection data were as follows:
1 H NMR(400MHz,CDCl 3 ):δ＝7.37(d,2H,J＝8.0Hz),7.21(d,2H,J＝8.4Hz),4.47(s,2H),3.53(t,2H,J＝7.2Hz),3.23(t,2H,J＝7.6Hz),1.33(s,9H)。
13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ＝172.2,150.9,133.0,128.0,125.8,48.4,48.1,34.6,31.4,25.5.HRMS(EI):C 14 H 20 ONS[M+H] + theoretical value of m/z: 250.1260, found: 250.1262.
example 5: synthetic method of 3- (4-bromobenzyl) thiazolidine-2-ketone
Figure BDA0002129711350000071
P-bromobenzyl bromide (136. Mu.L, 1 mmol), 2- (methylthio) -4,5-dihydrothiazole (56. Mu.L, 0.5 mmol), potassium tert-butoxide (56mg, 0.5 mmol), iodine (256 mg,1.0 mmol) and ethanol (1 ml) were sequentially added to a reaction tube, and the reaction was carried out with electromagnetic stirring at a reaction temperature of 80 ℃ for 20 hours. After the reaction was complete, the solvent was removed by rotary evaporation and the mixture was separated by column chromatography eluting with ethyl acetate and petroleum ether (1:9 by volume) to give a colorless liquid (96mg, 71%)
The product detection data were as follows:
1 H NMR(400MHz,CDCl 3 ):δ＝7.57(d,2H,J＝8.4Hz),7.15(d,2H,J＝8.4Hz),4.43(s,2H),3.50(t,2H,J＝7.2Hz),3.24(t,2H,J＝7.2Hz)。
13 C{ 1 H}NMR(100MHz,CDCl 3 ):δ＝172.4,135.2,132.0,129.9,121.9,48.1,48.0,25.6.HRMS(EI):C 10 H 11 ONBrS[M+H] + theoretical value of m/z: 271.9739, found: 271.9742.

Claims (8)

1. a synthesis method of thiazolidone compounds is characterized in that benzyl halide compounds and 2- (alkylthio) -4,5-dihydrothiazole are used as reaction raw materials, an alkali reagent and iodine are used as catalysts, and the thiazolidone compounds are obtained by a one-pot reaction in a solvent under the heating condition, wherein the thiazolidone compounds are prepared
The structural formula of the benzyl halide compound is
Figure FDA0003955078450000011
The structural formula of the 2- (alkylthio) -4,5-dihydrothiazole is shown in the specification
Figure FDA0003955078450000012
The structural formula of thiazolidone compound is
Figure FDA0003955078450000013
R has the following general formula:
Figure FDA0003955078450000014
R 0 is an alkyl group having 1 to 22 carbon atoms;
R 1 -R 5 independently selected from hydrogen, halogen, alkenyl, alkynyl, aryl, hydroxyl, amino, carboxyl, cyano, nitro or alkyl having 1 to 22 carbon atoms;
x is selected from halogen;
the alkali reagent is selected from one or more of potassium carbonate, potassium hydroxide, potassium acetate and potassium tert-butoxide;
the solvent is selected from one of dimethyl carbonate, toluene, carbon tetrachloride, ethanol, tetrahydrofuran and acetonitrile.
2. A method of synthesizing a thiazolidinone compound according to claim 1 wherein the base agent is potassium tert-butoxide.
3. A method for synthesizing a thiazolidinone compound according to claim 1 wherein the solvent is dimethyl carbonate.
4. A method of synthesizing thiazolidone compound according to claim 1 wherein the heating temperature is selected from 30 to 120 ℃ and the reaction time is 10 to 24 hours.
5. A method for synthesizing thiazolidone compound according to claim 1 wherein the heating temperature is selected from 80 to 100 ℃ and the reaction time is 16 to 20 hours.
6. A method of synthesizing thiazolidinone compound according to claim 1 wherein the molar ratio of benzyl halide compound, 2- (alkylthio) -4,5-dihydrothiazole, base reagent and iodine is 1:0.5:0.5:1.
7. a method of synthesizing a thiazolidinone compound according to claim 1 wherein R0 is selected from methyl.
8. A method of synthesizing thiazolidinone compound according to claim 1 wherein R 1 -R 5 At least 4 of them are selected from hydrogen atoms.
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