CN109232449A - A kind of preparation method of the novel trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5- - Google Patents
A kind of preparation method of the novel trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5- Download PDFInfo
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- CN109232449A CN109232449A CN201811070793.9A CN201811070793A CN109232449A CN 109232449 A CN109232449 A CN 109232449A CN 201811070793 A CN201811070793 A CN 201811070793A CN 109232449 A CN109232449 A CN 109232449A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Abstract
The invention belongs to technical field of organic synthesis, provide a kind of novel 5- sulfonyl-Isosorbide-5-Nitrae; 5- trisubstituted 1, the preparation method of 2,3- triazoles; in organic solvent, under four carbonyl dichloride rhodium dimer catalyst actions, thio interior alkynes compound and azide reaction are catalyzed; then m-chloro-benzoic acid peroxide is added; " one kettle way " prepares 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1; 2,3- triazoles.The preparation method reaction condition of 5- sulfonyl-Isosorbide-5-Nitrae in the present invention, trisubstituted 1,2,3- triazole product of 5- is mild, and product yield is not less than 55%.The reaction condition of the preparation method is mild, green, reaction efficiency is high, is more suitable for large-scale production requirement, the 5- sulfonyl-Isosorbide-5-Nitrae being prepared, 5- trisubstituted 1, and 2,3- triazole compounds have potential physiological activity.
Description
Technical field
The invention belongs to technical field of organic synthesis, are related to a kind of novel 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1,2,3-
The preparation method of triazole.
Background technique
Nitrine-alkynes cycloaddition reaction is to prepare one of most important method of 1,2,3- triazole.In recent years, has a system
Column document or the patent report preparation method of 1,2,3- triazole compound.
Since in the catalysis nitrine-Terminal Acetylenes cycloaddition reaction of copper in 2001 by Medal seminar and Sharpless project component
After Bao Dao not coming out (J.Org.Chem., 2002,67,3057 and Angew.Chem.Int.Ed., 2002,41,2596), this is anti-
It should be by extensive research and concern.But for alkynes cycloaddition reaction in nitrine-sulfonyl of copper catalysis, in many cases
Generate the trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5- and the trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5-
Mixture (J.Org.Chem.2008,73,8057).How the region choosing of nitrine-sulfonyl in alkynes cycloaddition reaction is changed
Selecting property is the emphasis that we pay close attention to.Although having the side of alkynes in some changes-nitrine cycloaddition reaction regioselectivity at present
Method is reported out, but for 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1, the technology of preparing of 2,3- triazoles is had not yet to see
Open report.The trisubstituted 1,2,3- triazole compound of 5- sulfonyl -1,4,5- is active important with potential source biomolecule
Compound, therefore research preparation method has important meaning.
It is raw material present invention employs various thio interior alkynes and organic azide, uses 2.5mol%
[Rh(CO)2Cl]2As catalyst, under conditions of 40 DEG C, reacts 12-24 hours, oxidant m-chloro is then added
Perbenzoic acid, in room temperature, the reaction was continued 3-12 hours, finally obtains 5- sulfonyl-Isosorbide-5-Nitrae, 5- with 55%~85% yield
Trisubstituted 1,2,3- triazole compound.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of trisubstituted tri- nitrogen of 1,2,3- of synthesis 5- sulfonyl -1,4,5-
The method of azole compounds.
Technical solution of the present invention:
A kind of novel 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1, the preparation method of 2,3- triazoles, steps are as follows:
In organic solvent, in four carbonyl dichloride rhodium dimer ([Rh (CO)2Cl]2) under catalyst action, be catalyzed thio
Then m-chloro-benzoic acid peroxide (m-CPBA) is added in interior alkynes compound and azide reaction, " one kettle way " prepares 5- sulphonyl
Base-Isosorbide-5-Nitrae, 5- trisubstituted 1,2,3- triazoles, reaction equation are as follows:
Wherein, R1And R2For alkyl, alkoxy or aryl, R1And R2It is identical or different；
R3For alkyl or aryl；
I is thio interior alkynes compound；
Reaction temperature is 25 DEG C~65 DEG C, and the reaction time is 8h~for 24 hours, and 5- sulfonyl-Isosorbide-5-Nitrae is prepared, and 5- tri- replaces
1,2,3- triazole.
The molar ratio of the thio interior alkynes compound and nitrine be 1:1.5, thio interior alkynes compound and
The molar ratio of chloro peroxide acid is 1:3, the concentration of thio interior alkynes compound
0.01-0.1mmol/ml。
[the Rh (CO)2Cl]2Dosage be thio interior alkynes compound 0.5~50mol%.
The organic solvent be benzene, toluene, ether, methyl tertiary butyl ether(MTBE), methylene chloride, tetrahydrofuran, benzotrifluoride,
The mixing of one or more of hexamethylene, petroleum ether, preferred solvent is methylene chloride, 1,2- dichloroethanes or chloroform.
Beneficial effects of the present invention: the trisubstituted 1,2,3- triazole product of 5- sulfonyl -1,4,5- in the present invention
Preparation method reaction condition is mild, and product yield is not less than 55%.The reaction condition of the preparation method is mild, green, reacts effect
Rate is high, is more suitable for large-scale production requirement, the 5- sulfonyl-Isosorbide-5-Nitrae being prepared, trisubstituted 1,2,3- triazole chemical combination of 5-
Object has potential physiological activity.
Specific embodiment
Below in conjunction with technical solution, a specific embodiment of the invention is further illustrated.
The preparation of embodiment 1:5- benzenesulfonyl-(1- benzyl) -4- phenyl -1H-1,2,3- triazole
Under air, 1- phenylacetylene base diphenyl sulfide (0.2mmol, 42.0mg) is dissolved in chloroform (2mL), adds benzyl
Nitrine (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C, reacts
Then m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) is added in 12h, react at room temperature 3h, and column chromatography for separation obtains after having reacted
To yellow solid product 62mg, yield 80%.
Mp=139-141 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.78 (d, J=8.0Hz, 2H), 7.58 (t, J=
8.0Hz, 1H), 7.52 (t, J=8.0Hz, 1H), 7.46-7.38 (m, 4H), 7.21 (t, J=8.0Hz, 1H), 7.19-7.13
(m, 2H), 6.84-6.79 (m, 4H), 4.34 (t, J=8.0Hz, 2H), 3.12 (t, J=8.0Hz, 2H)13C NMR(100MHz,
CDCl3):δ145.2,140.9,139.6,136.4,133.5,130.5,129.8,129.0,128.8,128.6,128.6,
127.8,127.1,124.1,49.9,36.3.HRMS(ESI-TOF)m/z calcd for C22H19N3O2S(M+Na)+
412.1090,found 412.1093.
The preparation of embodiment 2:5- benzenesulfonyl-(1- benzyl) -4- p-methoxyphenyl -1H-1,2,3- triazole
Under air, 1- is dissolved in chloroform (2mL) Methoxy-phenylacetylene base diphenyl sulfide (0.2mmol, 48.0mg), then
Benzyl azide (0.3mmol, 40.2mg) and [Rh (CO) is added2Cl]2(0.005mmol, 1.9mg) is stirred to react mixing at 40 DEG C
Object reacts 12h, and m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) then is added, and reacts at room temperature 3h, has reacted rear pillar layer
Analyse isolated colorless liquid product 61mg, yield 75%.
1HNMR(400MHz,CDCl3, TMS): δ 7.57 (d, J=8.0Hz, 2H), 7.42 (t, J=8.0Hz, 1H), 7.35-
7.33 (m, 5H), 7.18-7.12 (m, 4H), 6.96 (d, J=12.0Hz, 2H), 6.06 (s, 2H), 3.88 (s, 3H)13C NMR
(100MHz,CDCl3):δ160.7,150.1,140.0,134.7,133.9,131.8,131.5,128.9,128.8,128.5,
128.1,127.0,121.1,113.6,55.3,54.5.HRMS(ESI-TOF)m/z calcd for C22H19N3O3S(M+Na)+
428.1039,found 428.1043.
The preparation of embodiment 3:5- benzenesulfonyl-(1- benzyl) -4- p-bromophenyl -1H-1,2,3- triazole
Under air, 1- is dissolved in chloroform (2mL) bromobenzene acetylenylbenzene thioether (0.2mmol, 57.6mg), adds
Benzyl azide (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C,
12h is reacted, m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) then is added, reacts at room temperature 3h, has reacted rear pillar chromatography point
From obtaining white solid product 64mg, yield 71%.
Mp=141-143 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.57 (dd, J=12.0,8.0Hz, 4H), 7.44
(t, J=8.0Hz, 1H), 7.36-7.34 (m, 5H), 7.20-7.13 (m, 4H), 6.06 (s, 2H)13C NMR(100MHz,
CDCl3):δ149.0,139.7,134.5,134.2,132.5,131.7,131.4,129.0,128.9,128.6,128.1,
127.8,127.0,124.3,54.5.HRMS(ESI-TOF)m/z calcd for C21H16BrN3O2S(M+Na)+476.0039,
found 476.0042.
The preparation of embodiment 4:5- benzenesulfonyl-(1- benzyl) -4- normal-butyl -1H-1,2,3- triazole
Under air, 1- hexin base diphenyl sulfide (0.2mmol, 38.0mg) is dissolved in chloroform (2mL), it is folded adds benzyl
Nitrogen (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C, reacts
Then m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) is added in 12h, react at room temperature 3h, and column chromatography for separation obtains after having reacted
To colorless liquid product 51mg, yield 72%.
1H NMR(400MHz,CDCl3, TMS): δ 7.50 (t, J=8.0Hz, 1H), 7.43 (d, J=8.0Hz, 2H),
7.32-7.23 (m, 5H), 7.12 (d, J=8.0Hz, 2H), 5.90 (s, 2H), 2.95-2.91 (m, 2H), 1.76-1.68 (m,
2H), 1.42 (q, J=8.0Hz, 2H), 0.95 (t, J=8.0Hz, 3H)13C NMR(100MHz,CDCl3):δ151.9,
140.3,134.4,134.0,131.5,129.2,128.8,128.4,127.7,126.9,53.8,31.0,25.5,22.5,
13.8.HRMS(ESI-TOF)m/z calcd for C19H21N3O2S(M+Na)+378.1247,found 378.1249.
The preparation of embodiment 5:5- normal-butyl sulfonyl-(1- benzyl) -4- phenyl -1H-1,2,3- triazole
Under air, 1- phenylacetylene base n-butyl sulfide (0.2mmol, 38.0mg) is dissolved in chloroform (2mL), is added
Benzyl azide (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C,
12h is reacted, m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) then is added, reacts at room temperature 3h, has reacted rear pillar chromatography point
From obtaining colorless liquid product 60mg, yield 85%.
1H NMR(400MHz,CDCl3, TMS): δ 7.83-7.80 (m, 2H), 7.48 (t, J=8.0Hz, 3H), 7.44-
7.37 (m, 5H), 6.01 (s, 2H), 2.60-2.56 (m, 2H), 1.32-1.28 (m, 2H), 1.04 (q, J=8.0Hz, 2H),
0.64 (t, J=8.0Hz, 3H)13C NMR(100MHz,CDCl3):δ150.1,134.6,130.2,129.8,129.7,
128.9,128.9,128.8,128.5,128.3,55.9,54.4,23.6,21.0,13.2.HRMS(ESI-TOF)m/z calcd
for C19H21N3O2S(M+Na)+378.1247,found 378.1246.
The preparation of embodiment 6:5- benzenesulfonyl-(1- is to methylbenzyl) -4- phenyl -1H-1,2,3- triazole
Under air, it by 1- phenylacetylene base diphenyl sulfide (0.2mmol, 42.0mg), adds to methylbenzyl nitrine
(0.3mmol, 44.1mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C, reacts 12h,
Then m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) is added, reacts at room temperature 3h, column chromatography for separation obtains white after having reacted
Color solid product 55mg, yield 71%.
Mp=104-106 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.58 (d, J=8.0Hz, 2H), 7.46-7.41
(m, 4H), 7.26 (d, J=8.0Hz, 2H), 7.18-7.14 (m, 6H), 6.03 (s, 2H), 2.39 (s, 3H)13C NMR
(100MHz,CDCl3):δ150.2,139.9,138.4,133.9,132.3,131.7,130.1,129.6,129.5,128.8,
128.8,128.2,128.1,127.1,54.3,21.2.HRMS(ESI-TOF)m/z calcd for C22H19N3O2S(M+Na)+
412.1090,found 412.1091.
The preparation of embodiment 7:5- benzenesulfonyl-(1- p-chlorobenzyl) -4- phenyl -1H-1,2,3- triazole
Under air, by 1- phenylacetylene base diphenyl sulfide (0.2mmol, 42.0mg), p-chlorobenzyl nitrine is added
(0.3mmol, 50.1mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C, reacts 12h,
Then m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) is added, reacts at room temperature 3h, column chromatography for separation obtains white after having reacted
Color solid product 54mg, yield 66%.
Mp=1106-108 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.59 (d, J=8.0Hz, 2H), 7.47-7.40
(m,4H),7.34-7.28(m,4H),7.19-7.15(m,4H),6.03(s,2H).13C NMR(100MHz,CDCl3):δ
150.3,139.7,134.7,134.1,133.1,132.3,130.1,129.7,129.6,129.1,128.9,128.6,
128.2,127.0,53.8.HRMS(ESI-TOF)m/z calcd for C21H16ClN3O2S(M+Na)+432.0544,found
432.0545.
The system of embodiment 8:5- benzenesulfonyl-(1- para Toluic Acid carbomethoxy) -4- rubigan -1H-1,2,3- triazole
It is standby
Under air, 1- is added into para Toluic Acid's carbomethoxy to chlorobenzene acetylenylbenzene thioether (0.2mmol, 48.4mg)
Nitrine (0.3mmol, 53.1mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react mixture at 40 DEG C, reacts
Then m-chloro-benzoic acid peroxide (0.6mmol, 103.5mg) is added in 12h, react at room temperature 3h, and column chromatography for separation obtains after having reacted
To white solid product 50mg, yield 55%.
Mp=135-137 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.74 (d, J=12.0Hz, 2H), 7.31 (d, J
=8.0 Hz, 2H), 7.08-7.03 (m, 5H), 6.89-6.83 (m, 4H), 3.57 (s, 3H)13C NMR(100 MHz,
CDCl3):δ165.7,149.1,139.1,139.0,136.3,134.5,133.7,132.4,131.7,130.3,129.8,
129.1,128.5,127.7,127.1,52.7.HRMS(ESI-TOF)m/z calcd for C22H16ClN3O4S(M+Na)+
476.0443,found 476.0446.
Claims (8)
1. a kind of novel 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1, the preparation method of 2,3- triazoles, which is characterized in that step is such as
Under:
In organic solvent, in four carbonyl dichloride rhodium dimer [Rh (CO)2Cl]2Under catalyst action, it is catalyzed thio interior alkynes
Class compound and azide reaction, are then added m-chloro-benzoic acid peroxide m-CPBA, and " one kettle way " prepares 5- sulfonyl-Isosorbide-5-Nitrae, 5-
Trisubstituted 1,2,3- triazoles, reaction equation is as follows:
Wherein, R1And R2For alkyl, alkoxy or aryl, R1And R2It is identical or different；
R3For alkyl or aryl；
I is thio interior alkynes compound；
Reaction temperature is 25 DEG C~65 DEG C, and the reaction time is 8h~for 24 hours, is prepared 5- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1,
2,3- triazole.
2. novel 5- sulfonyl-Isosorbide-5-Nitrae according to claim 1,5- trisubstituted 1, the preparation method of 2,3- triazoles,
Be characterized in that, the molar ratio of the thio interior alkynes compound and nitrine is 1:1.5, thio interior alkynes compound and
The molar ratio of chloro peroxide acid is 1:3, the concentration 0.01-0.1mmol/ml of thio interior alkynes compound.
3. the preparation side of the novel trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5- according to claim 1 or 2
The method, which is characterized in that [Rh (CO)2Cl]2Dosage be thio interior alkynes compound 0.5~50mol%.
4. the preparation side of the novel trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5- according to claim 1 or 2
Method, which is characterized in that the organic solvent is benzene, toluene, ether, methyl tertiary butyl ether(MTBE), methylene chloride, tetrahydrofuran, three
The mixing of one or more of toluene fluoride, hexamethylene, petroleum ether.
5. novel 5- sulfonyl-Isosorbide-5-Nitrae according to claim 3,5- trisubstituted 1, the preparation method of 2,3- triazoles,
It is characterized in that, the organic solvent is benzene, toluene, ether, methyl tertiary butyl ether(MTBE), methylene chloride, tetrahydrofuran, fluoroform
The mixing of one or more of benzene, hexamethylene, petroleum ether.
6. according to claim 1, the preparation side of the novel trisubstituted 1,2,3- triazole of 5- sulfonyl -1,4,5- described in 2 or 5
Method, which is characterized in that the organic solvent is methylene chloride, 1,2- dichloroethanes or chloroform.
7. novel 5- sulfonyl-Isosorbide-5-Nitrae according to claim 3,5- trisubstituted 1, the preparation method of 2,3- triazoles,
It is characterized in that, the organic solvent is methylene chloride, 1,2- dichloroethanes or chloroform.
8. novel 5- sulfonyl-Isosorbide-5-Nitrae according to claim 4,5- trisubstituted 1, the preparation method of 2,3- triazoles,
It is characterized in that, the organic solvent is methylene chloride, 1,2- dichloroethanes or chloroform.
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| CN113501843A (en) * | 2021-05-27 | 2021-10-15 | 兰州大学 | Method for synthesizing trivalent phosphorus substituted amine compound |
| WO2023111869A1 (en) * | 2021-12-14 | 2023-06-22 | Nasim Batooie | Method for synthesizing an anti-cancer compound through a one-pot reaction |
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| CN106496086A (en) * | 2016-10-10 | 2017-03-15 | 沈阳药科大学 | The synthetic method of 4 methylsulfonyl butyl isothiocyanates |
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| CN106496086A (en) * | 2016-10-10 | 2017-03-15 | 沈阳药科大学 | The synthetic method of 4 methylsulfonyl butyl isothiocyanates |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113501843A (en) * | 2021-05-27 | 2021-10-15 | 兰州大学 | Method for synthesizing trivalent phosphorus substituted amine compound |
| CN113501843B (en) * | 2021-05-27 | 2023-06-02 | 兰州大学 | Synthesis method of trivalent phosphorus substituted amine compound |
| WO2023111869A1 (en) * | 2021-12-14 | 2023-06-22 | Nasim Batooie | Method for synthesizing an anti-cancer compound through a one-pot reaction |
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