CN109879832A - A kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation method - Google Patents
A kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation method Download PDFInfo
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Abstract
The present invention provides a kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation method, belong to heterocyclic compound synthesis technical field, the following steps are included: (1) is by 1, bis- sulphur -2 of 4-, halogenated -2- the arylacetamide of 5- glycol, N- alkoxy -2- and alkali are dissolved in solvent by the molar ratio of 0.5-1:1:1-2, carry out cyclization；(2) it adds oxidant and carries out oxidation reaction, to after the reaction was completed, remove solvent, obtain 4- alkoxy -2- aryl thiol morpholine -3,5- diketone.The present invention utilizes stable commercial reagents 1, bis- sulphur -2 of 4-, 5- glycol is as sulphur source, with the halogenated -2- arylacetamide of N- alkoxy -2- Cyclization 4- alkoxy -5- hydroxyl -2- aryl thiol morpholine -3- ketone in a mild condition, hydroxyl is reoxidized to synthesize to obtain 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds.Raw materials used simple and easy to get, stability is good, and reaction condition is mild, and easy to operate, by-product is few, substrate wide adaptability.
Description
Technical field
The invention belongs to heterocyclic compound synthesis technical fields, and in particular to a kind of 4- alkoxy -2- aryl thiol morpholine -
3,5- cyclohexadione compounds and preparation method.
Background technique
Sulfydryl morpholine -3,5- diketone is a kind of important heterocyclic compound, many compound tools containing this structural framework
There is certain physiological activity, such as Acta. Pol. Pharm. 2016,73,1181-1189 reports part sulfydryl morpholine-
3,5- derovatives have certain anti-microbial property to staphylococcus and Escherichia coli.In addition, sulfydryl morpholine -3,5- diketone is also
Modification group modification Glucosamine be can be used as glycosyl donor (Tetrahedron. Lett. 2000,41,629-
632).Sulfydryl morpholine -3,5- diketone mainly synthesizes thio Isosorbide-5-Nitrae-dioxanes -2,6 diketone by thiodiglycolic acid dehydration at present,
Then it is prepared again with amine generation aminolysis, condensation reaction, wherein dehydration synthesis Isosorbide-5-Nitrae-dioxanes -2,6 diketone needs that equivalent is added
Above dehydrating agent (acetic anhydride or trifluoro-acetic anhydride etc.), condensation step needs that condensing agent is added, and generates more waste and leads
Cause product purification difficult (J. Mol. Struct. 2015,1079,383-390)；Or by thioacetic acid or acetic acid esters,
Through with alpha-halogenate ester condensation, aminolysis, cyclization, oxidation and etc. synthesis, longer, the used thioacetic acid substance of hair reaction route
Toxicity with higher, stability is poor, and substrate diversity is also subject to certain restrictions.Due to above, these synthesis
Method limits the easy synthesis of sulfydryl morpholine -3,5- cyclohexadione compounds to a certain extent, and synthesis process is complicated, reacts
Journey is unstable.
Summary of the invention
In view of this, the present invention provides a kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation
Method, i.e., using stable-two sulphur -2,5- glycol of commercial reagents Isosorbide-5-Nitrae as sulphur source, with the halogenated -2- aryl of N- alkoxy -2-
Acetamide Cyclization 4- alkoxy -5- hydroxyl -2- aryl thiol morpholine -3- ketone in a mild condition reoxidizes hydroxyl synthesis
Obtain 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds.This method raw material stabilization is easy to get, and reaction condition is mild,
By-product is few, easily operated, and substrate adaptability is wider.
A kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation method, comprising the following steps:
(1) bis- sulphur -2,5- glycol of 1,4-, the halogenated -2- arylacetamide of N- alkoxy -2- and alkali are pressed into 0.5-1:1:
The molar ratio of 1-2 is dissolved in solvent, carries out cyclization, and reaction temperature is 35-100 DEG C, reaction time 8-48h；
(2) solid being filtered to remove in solution, obtains reaction mixture, adds oxidant and carries out oxidation reaction, is heated to reflux,
After the reaction was completed, evaporating solvent under reduced pressure, residue with Ethyl acetate and petroleum ether be eluant, eluent, silica gel column chromatogram separating purification,
Obtain 4- alkoxy -2- aryl thiol morpholine -3,5- diketone.
Wherein, the alkoxy can be one of methoxyl group, ethyoxyl, benzyloxy or a variety of, for example, alkoxy is
Methoxyl group.The aryl can be phenyl, 2- methoxyphenyl, 2- nitrobenzophenone, 4- fluorophenyl, 4- aminomethyl phenyl, 1- naphthalene
One of or it is a variety of, for example, aryl can be 2- methoxyphenyl.
Halogenated -2- the arylacetamide of N- alkoxy -2- can be the chloro- 2- phenyl-acetamides of N- benzyloxy -2-, N- methoxy
The chloro- 2- phenyl-acetamides of base -2-, the chloro- 2- phenyl-acetamides of N- ethyoxyl -2-, the chloro- 2-(4- fluorophenyl of N- benzyloxy -2-) second
Amide etc..
Effect of the alkali as catalyst used in step (1), the present invention in alkali can be inorganic base, such as sodium carbonate, carbon
One of sour potassium, sodium ethoxide are a variety of, or organic base, such as diisopropyl ethyl amine, 4-dimethylaminopyridine, three second
One of amine is a variety of.The effect of alkali be added is chiefly to facilitate the halogenated -2- arylacetamide of N- alkoxy -2- and sloughs one point
Sub- hydrogen halides forms aza allyl cation intermediate, and the attack for receiving sulfydryl occurs cyclization and generates product.
The solvent can for tetrahydrofuran, methylene chloride, chloroform, ethyl acetate, acetone, acetonitrile, dioxane,
One of toluene is a variety of.
Oxidant used in the present invention is one of pyridine chlorochromate drone salt (PCC), Dai Si-Martin's oxidant simultaneously
Or two kinds.
Reaction equation in the present invention is as follows；
Wherein, R1For methyl, ethyl, benzyl etc.；Ar is phenyl, 2- methoxyphenyl, 2- nitrobenzophenone, 4- fluorophenyl, 4- first
The aryl such as base phenyl, 1- naphthalene.
This reaction is possible, and the reaction mechanism is as follows shown in formula: in the presence of alkali, the halogenated -2- aryl second of N- alkoxy -2-
Amide dehydrohalogenation generates aza allyl cation reactive intermediate, meanwhile,-two sulphur -2,5- glycol depolymerization in a solvent of Isosorbide-5-Nitrae
Mercapto-acetaldehyde monomer is generated, nucleophilic addition, the nitrogen of generation occur for sulfydryl attack aza allyl cation reactive intermediate
Anion again attack mercapto-acetaldehyde aldehyde radical generate 4- alkoxy -5- hydroxyl -2- aryl thiol morpholine -3- ketone, in oxidant
Under effect, 5 hydroxyls are oxidized, and generate target product 4- alkoxy -2- aryl thiol morpholine -3,5- diketone.
Using stable-two sulphur -2,5- glycol of commercial reagents Isosorbide-5-Nitrae as sulphur source, with the halogenated -2- virtue of N- alkoxy -2-
Yl acetamide Cyclization 4- alkoxy -5- hydroxyl -2- aryl thiol morpholine -3- ketone in a mild condition reoxidizes hydroxyl conjunction
At obtaining 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds.Raw materials used simple and easy to get, stability is good, reaction
Mild condition, easy to operate, by-product is few, substrate wide adaptability.
Specific embodiment
The present invention will be described in detail With reference to embodiment.
The synthesis of one: 4- benzyloxy -2- phenylmercapto morpholine -3,5- diketone of embodiment；
The chloro- 2- phenyl-acetamides of N- benzyloxy -2- (137.9 mg, 0.5 mmol) is added in dry Schlenk pipe, 1,
Bis- sulphur -2,5- glycol of 4- (38 mg, 0.25 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride (5 mL), room
Temperature is lower to react 8 h.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 mL), PCC are added
(107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, and column chromatography for separation obtains product
97.2 mg are pale yellow oily liquid, yield 62%.
1 (400 MHz, CDCl3, TMS): δ = 7.56–7.54 (m, 2H), 7.40–7.34 (m, 6H),
7.28–7.25 (m, 2H), 5.07 (s, 2H), 4.84 (s, 1H), 3.56–3.45 ppm (m, 2H); 13C NMR
(100 MHz, CDCl3, TMS): δ = 166.4, 165.3, 133.7, 133.3, 130.2, 129.3, 129.2,
128.8, 128.6, 127.9, 78.4, 49.1, 30.9 ppm。
Change the alkali in the present embodiment into diisopropyl ethyl amine, 4-dimethylaminopyridine, by solvent change into tetrahydrofuran,
One of methylene chloride, chloroform, ethyl acetate, acetone, acetonitrile, dioxane, toluene change PCC into Dai Si-Martin
Oxidation, the result and the present embodiment of obtained product are close.
The synthesis of two: 4- methoxyl group -2- phenylmercapto morpholine -3,5- diketone of embodiment；
The chloro- 2- phenyl-acetamides of N- methoxyl group -2- (99.8 mg, 0.5 mmol) is added in dry Schlenk pipe, Isosorbide-5-Nitrae -
Two sulphur -2,5- glycol (76 mg, 0.5 mmol), sodium carbonate (106 mg, 1 mmol), methylene chloride (5 mL), at 100 DEG C
React 48 h.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 mL), PCC (107.8 are added
Mg, 0.5 mmol), it is heated to reflux 1 h, after complete reaction, decompression boils off solvent, and column chromatography for separation obtains 67.6 mg of product,
For faint yellow solid, yield 62%.
Fusing point 104-106oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 7.43–7.26 (m, 5H),
4.87 (s, 1H), 3.94 (s, 3H), 3.55–3.49 ppm (m, 2H); 13C NMR (100 MHz, CDCl3,
TMS): δ = 166.0, 164.9, 133.1, 129.2, 128.9, 127.8, 64.1, 48.8, 30.7 ppm。
Sodium carbonate in the present embodiment is changed into the yield and the present embodiment phase of the product that potassium carbonate or sodium ethoxide obtain
Closely.
The synthesis of three: 4- ethyoxyl -2- phenylmercapto morpholine -3,5- diketone of embodiment；
The chloro- 2- phenyl-acetamides of N- ethyoxyl -2- (106.9 mg, 0.5 mmol) is added in dry Schlenk pipe, 1,
Bis- sulphur -2,5- glycol of 4- (57 mg, 0.375 mmol), triethylamine (116.2 μ L, 0.7 mmol), methylene chloride (5
ML), 12 h are reacted at 50 DEG C.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 mL) is added,
PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, and column chromatography for separation must produce
84.2 mg of object is pale yellow oily liquid, yield 68%.
1 (400 MHz, CDCl3, TMS): δ = 7.32–7.28 (m, 5H), 4.80 (s, 1H), 4.05
(q, J = 7.2 Hz, 2H), 3.51–3.40 (m, 2H), 1.30 ppm (t, J = 7.2 Hz, 3H); 13C NMR
(100 MHz, CDCl3, TMS): δ = 165.3, 164.2, 132.2, 128.1, 127.8, 126.7, 76.4,
76.0, 75.7, 71.3, 47.8, 29.7, 12.3 ppm。
Example IV: 4- benzyloxy -2-(4- fluorophenyl) sulfydryl morpholine -3,5- diketone synthesis
The chloro- 2-(4- fluorophenyl of N- benzyloxy -2- is added in dry Schlenk pipe) and acetamide (146.9 mg, 0.5
Mmol),-two sulphur -2,5- glycol of Isosorbide-5-Nitrae (57 mg, 0.375 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride
(5 mL), reacts 12 h at room temperature.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 is added
ML), PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, column chromatography for separation
101.1 mg of product is obtained, is white solid, yield 61%.
Fusing point 122-124oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 7.56–7.53 (m, 2H),
7.40–7.38 (m, 3H), 7.26–7.22 (m, 2H), 7.07–7.03 (m, 2H), 5.07 (s, 2H), 4.81
(s, 1H), 3.62–3.47 ppm (m, 2H); 13C NMR (100 MHz, CDCl3, TMS): δ = 166.3,
165.0, 162.7 (J C–F = 247.2 Hz), 133.5, 130.2, 129.8 (J C–F = 8.8 Hz), 129.3,
129.0 (J C–F = 3.9 Hz), 128.5, 116.1 (J C–F = 22.1 Hz), 78.3, 48.5, 31.2 ppm。
Five: 4- benzyloxy -2-(4- aminomethyl phenyl of embodiment) sulfydryl morpholine -3,5- diketone synthesis；
The chloro- 2-(4- aminomethyl phenyl of N- benzyloxy -2- is added in dry Schlenk pipe) and acetamide (144.9 mg, 0.5
Mmol),-two sulphur -2,5- glycol of Isosorbide-5-Nitrae (57 mg, 0.375 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride
(5 mL), reacts 12 h at room temperature.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 is added
ML), PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, column chromatography for separation
106.4 mg of product is obtained, is white solid, yield 65%.
Fusing point 112-114oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 7.57–7.54 (m, 2H),
7.40–7.38 (m, 3H), 7.21–7.11 (m, 4H), 5.07 (s, 2H), 4.81 (s, 1H), 3.56–3.47
(m, 2H), 2.35 ppm (s, 3H); 13C NMR (100 MHz, CDCl3, TMS): δ = 166.5, 165.2,
138.8, 133.6, 130.1, 129.8, 128.5, 127.7, 78.3, 48.8, 30.9, 21.1 ppm。
Six: 4- benzyloxy -2-(2- nitrobenzophenone of embodiment) sulfydryl morpholine -3,5- diketone synthesis；
The chloro- 2-(2- nitrobenzophenone of N- benzyloxy -2- is added in dry Schlenk pipe) and acetamide (160.4 mg, 0.5
Mmol),-two sulphur -2,5- glycol of Isosorbide-5-Nitrae (57 mg, 0.375 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride
(5 mL), reacts 12 h at room temperature.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 is added
ML), PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, column chromatography for separation
100.4 mg of product is obtained, is white solid, yield 56%.
Fusing point 114-116oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 8.13 (d, J = 8.0 Hz,
1H), 7.61–7.53 (m, 4H), 7.41–7.38 (m, 3H), 7.24 (d, J = 7.6 Hz, 1H), 5.76 (s,
1H), 5.08 (dd, J 1 = 12.4 Hz, J 2 = 9.2 Hz, 2H), 3.81–3.52 ppm (m, 2H); 13C NMR
(100 MHz, CDCl3, TMS): δ = 165.7, 164.6, 148.1, 133.8, 133.5, 130.5, 130.2,
130.0, 129.3, 129.2, 128.5, 126.2, 78.5, 46.2, 32.2 ppm。
Seven: 4- benzyloxy -2-(2- methoxyphenyl of embodiment) sulfydryl morpholine -3,5- diketone synthesis；
The chloro- 2-(2- methoxyphenyl of N- benzyloxy -2- is added in dry Schlenk pipe) and acetamide (160.4 mg, 0.5
Mmol),-two sulphur -2,5- glycol of Isosorbide-5-Nitrae (57 mg, 0.375 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride
(5 mL), reacts 12 h at room temperature.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 is added
ML), PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, column chromatography for separation
123.6 mg of product is obtained, is faint yellow solid, yield 72%.
Fusing point 170-172oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 7.58–7.55 (m, 2H),
7.40–7.38 (m, 3H), 7.36–7.31 (m, 1H), 7.01–7.00 (m, 1H), 6.95–6.90 (m, 2H),
5.18 (s, 1H), 5.08 (s, 2H), 3.85 (s, 3H), 3.65–3.56 ppm (m, 2H); 13C NMR (100
MHz, CDCl3, TMS): δ = 166.8, 165.6, 156.7, 133.8, 130.3, 130.2, 129.2, 128.8,
123.0, 120.8, 111.5, 78.3, 55.8, 44.2, 31.6 ppm。
Eight: 4- benzyloxy -2-(2- methoxyphenyl of embodiment) sulfydryl morpholine -3,5- diketone synthesis；
The chloro- 2-(1- naphthalene of N- benzyloxy -2- is added in dry Schlenk pipe) and acetamide (162.9 mg, 0.5
Mmol),-two sulphur -2,5- glycol of Isosorbide-5-Nitrae (57 mg, 0.375 mmol), triethylamine (83 μ L, 0.5 mmol), methylene chloride
(5 mL), reacts 12 h at room temperature.After fully reacting, with short silicagel column quick separating intermediate, methylene chloride (5 is added
ML), PCC (107.8 mg, 0.5 mmol), is heated to reflux 1 h, and after complete reaction, decompression boils off solvent, column chromatography for separation
119.9 mg of product is obtained, is pale pink solid, yield 66%.
Fusing point 151-153oC; 1H NMR (400 MHz, CDCl3, TMS): δ = 7.91–7.84 (m, 3H),
7.60–7.51 (m, 4H), 7.42–7.38 (m, 3H), 7.36–7.32 (m, 1H), 7.12 (d, J = 6.8 Hz,
1H), 5.54 (s, 1H), 5.15 (s, 2H), 3.61–3.50 ppm (m, 2H); 13C NMR (100 MHz,
CDCl3, TMS): δ = 166.6, 165.2, 134.4, 133.6, 130.4, 130.2, 130.0, 129.4,
129.3, 128.5, 126.8, 126.3, 125.7, 124.7, 123.2, 78.4, 46.8, 31.2 ppm。
The present invention utilizes stable-two sulphur -2,5- glycol of commercial reagents Isosorbide-5-Nitrae as sulphur source, with N- alkoxy -2- halogen
Generation -2- arylacetamide Cyclization 4- alkoxy -5- hydroxyl -2- aryl thiol morpholine -3- ketone in a mild condition, reoxidizes
Hydroxyl synthesizes to obtain 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds.It is raw materials used simple and easy to get, stability
Good, reaction condition is mild, and easy to operate, by-product is few, substrate wide adaptability, can be to contain sulfydryl morpholine -3,5- diketone or class
An alternative synthetic route is provided like the drug molecule of structure fragment.
The present invention is not limited to above-mentioned specific embodiment, and the invention may be variously modified and varied.All foundations
Technical spirit of the invention should be included in the present invention to embodiment of above any modification, equivalent replacement, improvement and so on
Protection scope.
Claims (8)
1. a kind of 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds and preparation method, which is characterized in that including
Following steps:
(1) by bis- sulphur -2,5- glycol of 1,4-, the halogenated -2- arylacetamide of N- alkoxy -2- and alkali rubbing by 0.5-1:1:1-2
You are dissolved in solvent ratio, carry out cyclization；
(2) it adds oxidant and carries out oxidation reaction, to after the reaction was completed, remove solvent, obtain 4- alkoxy -2- aryl thiol
Morpholine -3,5- diketone.
2. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the alkoxy is one of methoxyl group, ethyoxyl, benzyloxy or a variety of.
3. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the aryl is phenyl, 2- methoxyphenyl, 2- nitrobenzophenone, 4- fluorophenyl, 4- aminomethyl phenyl, 1- naphthalene
One of or it is a variety of.
4. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the alkali is one of sodium carbonate, potassium carbonate, sodium ethoxide or a variety of.
5. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the alkali is one of diisopropyl ethyl amine, 4-dimethylaminopyridine, triethylamine or a variety of.
6. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the solvent be tetrahydrofuran, methylene chloride, chloroform, ethyl acetate, acetone, acetonitrile, dioxane,
One of toluene is a variety of.
7. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, the oxidant is one or both of pyridine chlorochromate drone salt, Dai Si-Martin's oxidant.
8. 4- alkoxy -2- aryl thiol morpholine -3,5- cyclohexadione compounds according to claim 1 and preparation method,
It is characterized in that, reaction temperature described in step (1) is 35-100 DEG C, reaction time 8-48h.
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