CN109096214A - A kind of preparation method of the novel trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5- - Google Patents
A kind of preparation method of the novel trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5- Download PDFInfo
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- CN109096214A CN109096214A CN201811070787.3A CN201811070787A CN109096214A CN 109096214 A CN109096214 A CN 109096214A CN 201811070787 A CN201811070787 A CN 201811070787A CN 109096214 A CN109096214 A CN 109096214A
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- 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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Abstract
The invention belongs to technical field of organic synthesis, provide a kind of novel 4- sulfonyl-Isosorbide-5-Nitrae; 5- trisubstituted 1; the preparation method of 2,3- triazoles, steps are as follows: in organic solvent; under four carbonyl dichloride rhodium dimer catalyst actions; it is catalyzed alkynes compound and nitrine in sulfonyl and prepares 4- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1; 2,3- triazoles.The preparation method reaction condition of 4- 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 70%.The reaction condition of the preparation method is mild, green, reaction efficiency is high, is more suitable for large-scale production requirement, the 4- 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 4- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1,2,3-
The preparation method of triazole.
Background technique
According to the literature, 4- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1,2,3- triazole compounds have excellent resist
Bacterium, the bioactivity such as anti-infective and anti-oxidant, be a kind of important drug mother nucleus structure (Med.Chem.Commun.2017,8,
2258 and Eur.J.Med.Chem.2016,112,60).But how to efficiently synthesize the trisubstituted 1,2,3- of 4- sulfonyl -1,4,5-
Triazole compound is still a problem to be solved.
The methods of organic catalysis and multi-component reaction are used for the trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5-
Compound, but it is long there is the reaction time, and reaction process is cumbersome, the shortcomings such as severe reaction conditions (Org.Lett.2015,
17,6206 and Angew.Chem.Int.Ed.2014,53,10155).Therefore high regioselectivity is closed in a mild condition for development
There is important scientific meaning and practical application valence at the trisubstituted 1,2,3- triazole compound of 4- sulfonyl -1,4,5-
Value.
Nitrine-alkynes cycloaddition reaction is to prepare one of most important method of 1,2,3- triazole.But it is interior for nitrine-
Alkynes cycloaddition, there is reaction temperature height, and the reaction time is long, a series of disadvantages such as reaction product complexity.In recent years, our classes
Topic group primary study passes through the transition metal-catalyzed regioselectivity problem for changing the interior alkynes cycloaddition reaction of nitrine-.Although mesh
The method that alkynes in some changes-nitrine cycloaddition reaction regioselectivity has also been developed in other preceding seminars, but by folded
The interior alkynes cycloaddition reaction of nitrogen-prepares the technical method of the trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5- at present still
Not disclosed report.
It is raw material present invention employs alkynes in various sulfonyls and organic azide, uses 2.5mol% [Rh
(CO)2Cl]2As catalyst, under conditions of 40 DEG C, 4- sulfonyl-Isosorbide-5-Nitrae is obtained with 70%~88% yield, 5- tri- replaces
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 4- sulfonyl -1,4,5-
The method of azole compounds.
Technical solution of the present invention:
A kind of novel 4- 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, it is catalyzed sulphonyl
Alkynes compound and nitrine preparation 4- sulfonyl-Isosorbide-5-Nitrae, 5- trisubstituted 1,2,3- triazoles, reaction equation are as follows in base:
Wherein, R1And R2For alkyl, alkoxy or aryl, R1And R2It is identical or different；
R3For alkyl or aryl；
I is alkynes compound in sulfonyl；
Reaction temperature is 25 DEG C~65 DEG C, and the reaction time is 8h~for 24 hours, and the 4- sulphonyl that yield is not less than 70% is prepared
The trisubstituted 1,2,3- triazole of base -1,4,5-.
Alkynes compound and the molar ratio of nitrine are 1:1.5, alkynes compound in sulfonyl in the sulfonyl
Concentration 0.01-0.1mmol/ml.
[the Rh (CO)2Cl]2Dosage be sulfonyl in 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 are methylene chloride, 1,2- dichloroethanes or chloroform.
Beneficial effects of the present invention: the trisubstituted 1,2,3- triazole product of 4- sulfonyl -1,4,5- in the present invention
Preparation method reaction condition is mild, and product yield is not less than 70%.The reaction condition of the preparation method is mild, green, reacts effect
Rate is high, is more suitable for large-scale production requirement, the 4- 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 1:4- benzenesulfonyl-(1- benzyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl phenylacetylene (0.2mmol, 48.4mg) is dissolved in 1,2- dichloroethanes (2mL), 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 column chromatography for separation obtains colorless oil as product 61mg, yield 81% after having reacted.
1H NMR(400MHz,CDCl3, TMS): δ 7.79 (d, J=8.0Hz, 2H), 7.55-7.50 (m, 2H), 7.44-
7.39 (dd, J=12.0,8.0Hz, 4H), 7.24-7.19 (m, 3H), 7.11 (d, J=8.0Hz, 2H), 6.93 (d, J=
8.0Hz,2H),5.32(s,2H).13C NMR(100MHz,CDCl3):δ145.9,140.8,139.3,134.0,133.8,
130.9,130.2,129.2,129.0,128.9,128.8,128.1,128.0,124.4,52.8.
The preparation of embodiment 2:4- benzenesulfonyl-(1- is to methylbenzyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl phenylacetylene (0.2mmol, 48.4mg) is dissolved in 1,2- dichloroethanes (2mL), then plus
Enter to methylbenzyl nitrine (0.3mmol, 44.1mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C
Mixture reacts 12h, and column chromatography for separation obtains white solid product 59mg, yield 76% after having reacted.
Mp=147-149 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.83 (d, J=8.0Hz, 2H), 7.57 (t, J=
8.0Hz, 2H), 7.50-7.43 (m, 4H), 7.17 (d, J=8.0Hz, 2H), 7.05 (d, J=8.0Hz, 2H), 6.87 (d, J=
8.0Hz,2H),5.31(s,2H),2.31(s,3H).13C NMR(100MHz,CDCl3):δ145.7,140.7,139.1,
138.6,133.6,130.8,130.7,130.1,129.5,129.0,128.7,128.0,127.8,124.3,52.4,
21.1.HRMS(ESI-TOF)m/z calcd for C22H19N3O2S(M+Na)+412.1090,found 412.1094.
The preparation of embodiment 3:4- benzenesulfonyl-(1- p-chlorobenzyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl phenylacetylene (0.2mmol, 48.4mg) is dissolved in 1,2- dichloroethanes (2mL), then
P-chlorobenzyl nitrine (0.3mmol, 50.1mg) and [Rh (CO) is added2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C
Mixture reacts 12h, and column chromatography for separation obtains yellow solid product 57mg, yield 70% after having reacted.
Mp=132-134 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.83 (d, J=8.0Hz, 2H), 7.58 (t, J=
8.0Hz, 2H), 7.50-7.45 (m, 4H), 7.22 (d, J=8.0Hz, 2H), 7.15 (d, J=8.0Hz, 2H), 6.91 (d, J=
8.0Hz,2H),5.32(s,2H).13C NMR(100MHz,CDCl3):δ145.9,140.6,139.1,134.8,133.7,
132.2,130.9,130.0,129.3,129.1,128.8,128.0,124.1,51.9.HRMS(ESI-TOF)m/z calcd
for C21H16ClN3O2S(M+Na)+432.0544,found 432.0546.
The preparation of embodiment 4:4- benzenesulfonyl-(1- phenethyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl phenylacetylene (0.2mmol, 48.4mg) is dissolved in 1,2- dichloroethanes (2mL), then
Phenethyl nitrine (0.3mmol, 44.1mg) and [Rh (CO) is added2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C mixed
Object is closed, 12h is reacted, column chromatography for separation obtains yellow solid product 62mg, yield 80% after having reacted.
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 5:4- benzenesulfonyl-(1- benzyl) -5- p-methoxyphenyl -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl is dissolved in 1,2- dichloroethanes to Methoxy-phenylacetylene (0.2mmol, 54.4mg)
In (2mL), benzyl azide (0.3mmol, 40.2mg) and [Rh (CO) are added2Cl]2(0.005mmol, 1.9mg) is stirred at 40 DEG C
Reaction mixture is mixed, 12h is reacted, column chromatography for separation obtains yellow solid product 71mg, yield 88% after having reacted.
Mp=132-134 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.85 (d, J=8.0Hz, 2H), 7.59-7.56
(m, 1H), 7.48-7.44 (m, 2H), 7.28-7.25 (m, 3H), 7.10 (d, J=8.0Hz, 2H), 7.02-6.97 (m, 4H),
5.36(s,2H),3.90(s,3H).13C NMR(100MHz,CDCl3):δ161.4,145.6,140.8,139.2,134.0,
133.6,131.5,129.1,128.9,128.6,128.0,127.7,115.8,114.3,55.4,52.5.HRMS(ESI-TOF)
m/z calcd for C22H19N3O3S(M+Na)+428.1039,found 428.1043.
The preparation of embodiment 6:4- benzenesulfonyl-(1- benzyl) -5- rubigan -1H-1,2,3- triazole
Under air, 1- benzenesulfonyl is dissolved in 1,2- dichloroethanes (2mL) to chlorobenzene acetylene (0.2mmol, 55.2mg)
In add benzyl azide (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C
Mixture reacts 12h, and column chromatography for separation obtains white solid product 66mg, yield 81% after having reacted.
Mp=163-165 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.82 (d, J=8.0Hz, 2H), 7.56 (t, J=
8.0Hz, 1H), 7.44-7.40 (m, 4H), 7.25-7.21 (m, 3H), 7.06 (d, J=8.0Hz, 2H), 6.95-6.93 (m,
2H),5.32(s,2H).13C NMR(100MHz,CDCl3):δ146.0,140.5,138.0,137.2,133.8,133.7,
131.4,129.2,129.1,129.0,128.8,128.0,127.8,122.7,52.8.HRMS(ESI-TOF)m/z calcd
for C21H16ClN3O2S(M+Na)+432.0544,found 432.0542.
The preparation of embodiment 7:4- isopropelsulfonyl-(1- benzyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- isopropelsulfonyl phenylacetylene (0.2mmol, 41.6mg) is dissolved in 1,2- dichloroethanes (2mL)
In add benzyl azide (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C
Mixture reacts 12h, and column chromatography for separation obtains white solid product 51mg, yield 75% after having reacted.
Mp=113-115 DEG C of1H NMR(400MHz,CDCl3, TMS): δ 7.52 (t, J=8.0Hz, 1H), 7.45 (t, J=
8.0Hz,2H),7.29-7.23(m,5H),6.99-6.97(m,2H),5.43(s,2H),3.45-3.39(m,1H),1.29(d,J
=4.0Hz, 6H)13C NMR(100MHz,CDCl3):δ142.1,140.6,134.0,130.7,130.1,128.9,128.7,
128.7,127.7,124.1,55.3,52.7,15.2.HRMS(ESI-TOF)m/z calcd for C18H19N3O2S(M+Na)+
364.1090,found 364.1093.
The preparation of embodiment 8:4- normal-butyl sulfonyl-(1- benzyl) -5- phenyl -1H-1,2,3- triazole
Under air, 1- normal-butyl sulfonyl phenylacetylene (0.2mmol, 44.4mg) is dissolved in 1,2- dichloroethanes (2mL)
In add benzyl azide (0.3mmol, 40.2mg) and [Rh (CO)2Cl]2(0.005mmol, 1.9mg) is stirred to react at 40 DEG C
Mixture reacts 12h, and column chromatography for separation obtains colorless liquid product 51mg, yield 72% after having reacted.
1H NMR(400MHz,CDCl3, TMS): δ 7.55 (t, J=8.0Hz, 1H), 7.47 (t, J=8.0Hz, 2H),
7.31-7.26(m,5H),7.03-7.01(m,2H),5.45(s,2H),3.34-3.30(m,2H),1.77-1.71(m,2H),
1.41 (q, J=8.0Hz, 2H), 0.90 (t, J=8.0Hz, 3H)13C NMR(100MHz,CDCl3):δ144.0,139.5,
134.0,130.8,130.1,128.9,128.8,128.7,127.7,124.1,56.2,52.7,24.1,21.5,13.5.HRMS
(ESI-TOF)m/z calcd for C19H21N3O2S(M+Na)+378.1247,found 378.1249.
Claims (8)
1. a kind of novel 4- 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 the action of catalyst, it is catalyzed in sulfonyl
Alkynes compound and nitrine preparation 4- sulfonyl-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 alkynes compound in sulfonyl；
Reaction temperature is 25 DEG C~65 DEG C, and the reaction time is 8h~for 24 hours, and the 4- sulfonyl-that yield is not less than 70% is prepared
The trisubstituted 1,2,3- triazole of 1,4,5-.
2. novel 4- sulfonyl-Isosorbide-5-Nitrae according to claim 1,5- trisubstituted 1, the preparation method of 2,3- triazoles,
It is characterized in that, alkynes compound and the molar ratio of nitrine are 1:1.5, alkynes compound in sulfonyl in the sulfonyl
Concentration 0.01-0.1mmol/ml.
3. the preparation side of the novel trisubstituted 1,2,3- triazole of 4- sulfonyl -1,4,5- according to claim 1 or 2
The method, which is characterized in that [Rh (CO)2Cl]2Dosage be sulfonyl in alkynes compound 0.5~50mol%.
4. the preparation side of the novel trisubstituted 1,2,3- triazole of 4- 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 4- 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 4- 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 4- 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 4- 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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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746365A (en) * | 2019-11-04 | 2020-02-04 | 大连理工大学 | Preparation method of novel 4-thiocyano-1, 4, 5-trisubstituted 1,2, 3-triazole |
-
2018
- 2018-09-14 CN CN201811070787.3A patent/CN109096214A/en active Pending
Non-Patent Citations (3)
| Title |
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| ACS.REGISTRY DATABASE: "对比文件2", 《STNEXT》 * |
| WANGZE SONG ET AL.: "Rhodium(I)-Catalyzed Azide-Alkyne Cycloaddition (RhAAC) of Internal Alkynylphosphonates with High Regioselectivities under Mild Conditions", 《ADV. SYNTH. CATAL.》 * |
| YUN LIAO ET AL.: "Rhodium-Catalyzed Azide-Alkyne Cycloaddition of Internal Ynamides: Regioselective Assembly of 5-Amino-Triazoles under Mild Conditions", 《ACS CATAL.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746365A (en) * | 2019-11-04 | 2020-02-04 | 大连理工大学 | Preparation method of novel 4-thiocyano-1, 4, 5-trisubstituted 1,2, 3-triazole |
| WO2021088296A1 (en) * | 2019-11-04 | 2021-05-14 | 大连理工大学 | Novel preparation method for 4-thiocyano-1,4,5-trisubstituted 1,2,3-triazole |
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