CN107674036A - Asymmetric double 1,2,3 triazole compounds and its preparation method and application - Google Patents

Asymmetric double 1,2,3 triazole compounds and its preparation method and application Download PDF

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CN107674036A
CN107674036A CN201710718659.4A CN201710718659A CN107674036A CN 107674036 A CN107674036 A CN 107674036A CN 201710718659 A CN201710718659 A CN 201710718659A CN 107674036 A CN107674036 A CN 107674036A
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triazole compounds
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毕晶晶
李琳琳
张贵生
郝玉伟
谭强
荣德钦
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Henan Normal University
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Abstract

The invention discloses a kind of asymmetric double 1,2,3 triazole compounds and its preparation method and application, belong to the synthesis technical field of medicine intermediate.Technical scheme main points are：Asymmetric double 1,2,3 triazole compounds, its structural formula are：The invention further particularly discloses the preparation method of double 1,2,3 triazole compounds of the asymmetry and its application in fluorescence chemical sensor.The present invention by two different chromophores of click reaction formings first using binaphthyl as parent nucleus, to synthesize a series of asymmetric double 1,2,3 triazole compounds, such compound is in DMSO H2Ca is added in O systems2+Fluorescence intensity can be greatly enhanced, and then can realized in DMSO H2O systems are for Ca2+Quantitative detection.

Description

Asymmetric double -1,2,3- triazole compounds and its preparation method and application
Technical field
The invention belongs to the synthesis technical field of medicine intermediate, and in particular to and a kind of asymmetric double -1,2,3- triazoles Class compound and its preparation method and application.
Background technology
It is current research and the wider C of application with photoactive 1,1 '-union -2-naphthol and its derivative2Axle is not Symmetrical aromatic compound, its structure are regarded as the extension of central chirality, containing multiple chiral (R) or (S) -2,2 '-dinaphthol (BINOL) rotation of two naphthalene nucleus of derivative, which is restricted, makes molecule have good structural stability, dinaphthalene fluorogen Hypersensitivity makes molecule have identification basis well, and the special groups connected on naphthalene nucleus can greatly strengthen its chiral Recognition energy Power[1].These characteristics cause 1,1 '-union -2-naphthol derivative molecular to be used as a kind of effectively sensitive fluorescence chemical sensing Device[2].When being interacted with numerous heavy metal cations, the fluorescence chemical sensor is in different recognition site Receiued objects point Son, the change of energy level in conjugated polymer is caused by Photo-induced electron transfer (PET) or photoinduced charge transfer (PCT), is made Obtain all these interactions very delicately to reflect in its luminous intensity and energy, effectively show chemical sensor In the feature such as fluorescence intensity enhancing or the change of decrease and launch wavelength.
2001, Sharpless etc. proposed " click chemistry " (Click Chemistry) concept[2].This kind of reaction It is easily operated, and energy high productivity generation target product, seldom even without accessory substance, go on well under a number of conditions (logical It is especially good in Chang Shui), and will not be influenceed by other functional groups being connected together.Because 1,2,3- triazole structures contain Three nitrogen-atoms, can be as good coordinating group, and can be reacted and efficiently synthesized by click, therefore in fluorescence probe Synthesis and exploitation in, be increasingly taken seriously.Wherein this kind of fluorescence based on FRET (FRET) principle is visited Pin is most containing symmetrical or two fluorogens of identical, and modification difficulty is higher, synthesis step is longer, and only structure is relatively simple Single triazole fluorescence probe is succeeded development and application.
Inventor seminar is directed to preparation and the performance study of triazole compound of the research with structure diversity. Therefore based on dinaphthalene be parent nucleus, prepares a series of -1,2,3- triazole fluorescence probes of asymmetry pair, and have studied it tentatively Fluorescence property.Present patent application has obtained state natural sciences fund (21702051), He'nan Normal University doctor starts problem (qd15108), He'nan Normal University youth science fund (2016QK10), the key research project plan of institution of higher education of Henan Province (17A350006) and Environmental Chemistry and the subsidy and support of ecological toxicology National Key Laboratory (KF2016-01).
[1]Pu L.Chem.Rev.,2004,104:1687-1716；
[2]Chen Y,Yekta S,Yudin AK.Chem.Rev.,2003,103:3155-3211；
[3]Kolb H C,Finn M G,Sharpless K B.Angew.Chem.Int.Ed.,2001,40:2004- 2021。
The content of the invention
Present invention solves the technical problem that it there is provided a kind of asymmetric double -1,2,3- triazole compounds and its preparation Method, this method synthesize a series of asymmetry using binaphthyl as parent nucleus, by two different chromophores of click reaction formings Double -1,2,3- triazole compounds, such compound can be realized in DMSO-H2O systems are for Ca2+Quantitative detection.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, asymmetric double -1,2,3- triazole chemical combination Thing, it is characterised in that its structural formula is：
Wherein Ar and Ar ' is the combination of following structure and Ar is different from Ar '：
Of the present invention asymmetric double -1, the preparation method of 2,3- triazole compounds, it is characterised in that specific step Suddenly it is：
The halogenated aromatic compound of (1) two kind of different structure is folded with reaction of sodium azide two kinds of different structures of generation respectively Nitrogen aryl compound；
(2) 1,1 '-union -2-naphthols react to obtain the dinaphthalene compound of propargyl substitution with propargyl bromide；
(3) the dinaphthalene compound of propargyl substitution and a kind of structure nitrine aryl compound are in SODIUM ASCORBATE and mantoquita In the presence of react after, then with another structure nitrine aryl compound in the presence of SODIUM ASCORBATE and mantoquita the system of reacting Obtain asymmetric double -1,2,3- triazole compounds.
Further preferably, the detailed process of step (1) is：The halogenated aromatic compound of two kinds of different structures is separately added into Into differential responses container and DMF dissolving is added, Sodium azide is added under stirring state, room temperature reaction is stayed overnight, TLC monitoring raw material reactions are complete, and reaction is extracted after terminating with dichloromethane, and organic phase is dried, and vacuum rotary steam removes solvent, post layer Analyse the nitrine aryl compound of isolated two kinds of different structures.
Further preferably, the detailed process of step (2) is：In reaction vessel add (R)-(1,1- binaphthalenes) -2,2 ' - Glycol is simultaneously dissolved with acetonitrile, adds potassium carbonate and 3- propargyl bromides and in 85 DEG C of back flow reactions, TLC detection reactions terminate, organic Mutually dry, vacuum rotary steam removes solvent, and column chromatography for separation obtains the dinaphthalene compound of propargyl substitution.
Further preferably, the detailed process of step (3) is：By the dinaphthalene compound that propargyl substitutes and a kind of structure nitrine Aryl compound is dissolved in tetrahydrofuran, sequentially adds water, cupric sulfate pentahydrate and L-AA sodium salt, and room temperature lucifuge is anti- Should, TLC shows that initial feed disappears substantially, and reaction solution is extracted with dichloromethane, collects and dries organic phase, and vacuum rotary steam removes molten Agent, column chromatography for separation obtains target compound, then target compound and another structure nitrine aryl compound are dissolved in into four In hydrogen furans, water, cupric sulfate pentahydrate and L-AA sodium salt, the reaction of room temperature lucifuge are sequentially added, TLC shows initial feed base This disappearance, reaction solution are extracted with dichloromethane, are collected and are dried organic phase, and vacuum rotary steam removes solvent, and column chromatography for separation obtains mesh Mark the asymmetric double -1,2,3- triazole compounds of product.
The asymmetric double applications of -1,2,3- triazole compounds in fluorescence chemical sensor of the present invention.
Asymmetric double -1,2,3- triazole compounds of the present invention are as fluorescence chemical sensor in DMSO-H2O Ca is quantitatively detected in system2+In application, wherein Ca2+Detectable concentration scope be 5 × 10-6-5×10-4mol/L。
The present invention is first so that using binaphthyl as parent nucleus, a system is synthesized by two different chromophores of click reaction formings Row asymmetric double -1,2,3- triazole compounds, such compound is in DMSO-H2Ca is added in O systems2+Fluorescence can be made strong Degree greatly enhances, and then can realize in DMSO-H2O systems are for Ca2+Quantitative detection.
Embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair Bright scope.
1st, embodiments of the invention presented below (by taking as above compound 5 as an example)：
(1) synthesis of compound 9- (azido methyl) anthracene 1
9- chloromethyls anthracene (1g, 4.41mmol) is added in 50mL round-bottomed flask, adds 20mL N, N- dimethyl methyls Acid amides (DMF) dissolves, and Sodium azide (0.43g, 6.615mmol) is slowly added under stirring state, overnight, TLC is monitored for room temperature reaction Reaction is complete to raw material reaction, and reaction is extracted after terminating with dichloromethane, and organic phase is dried, and vacuum rotary steam removes solvent, post layer Analyse isolated yellow solid 1 (974.4mg, 95%).
(2) synthesis of compound nitrine methanonaphthalene 2
2- bromomethyls naphthalene (1g, 4.52mmol) is added in 50mL round-bottomed flask, adds 20mL DMF stirring and dissolvings, slowly Sodium azide (0.441g, 6.78mmol) is added, overnight, TLC monitorings reaction is complete to raw material reaction, after reaction terminates for room temperature reaction Extracted with dichloromethane, organic phase dry, vacuum rotary steam remove solvent, column chromatography for separation obtain yellow solid 2 (794.4mg, 96%).
(3) synthesis of compound (R) -2,2 '-bis- (2-propynyl -1- epoxides) -1,1 '-binaphthalene 3
(R)-(1,1- binaphthalene) -2 is added in 250mL round-bottomed flasks, 2 '-glycol (5g, 17.45mmol) is used in combination 100mL acetonitriles dissolve, and add potassium carbonate (4.85g, 34.9mmol) and 3- propargyl bromides (3.88mL, 52.35mmol) and in 85 DEG C back flow reaction, TLC detection reactions terminate, and organic phase is dried, and vacuum rotary steam removes solvent, and column chromatography for separation obtains pale yellow colored solid Body 3 (5.69g, 90%).
(4) compound (R) -1- (naphthalene -2- ylmethyls) -4- (((2'- (propyl- 2- alkynes -1- bases epoxide)-[1,1'- dinaphthalenes] - 2- yls) epoxide) methyl) and -1H-1,2,3- triazoles 4 synthesis
Compound 2 (100mg, 0.55mmol) and compound 3 (237mg, 0.655mmol) are dissolved in 10mL tetrahydrofurans (THF) in, water (10mL), cupric sulfate pentahydrate (13.12mg, 0.082mmol) and L-AA sodium salt are sequentially added (32.4mg, 0.164mmol), the reaction of room temperature lucifuge, TLC show that initial feed disappears substantially, and reaction solution is extracted with dichloromethane, Collect and dry organic phase, vacuum rotary steam removes solvent, and column chromatography for separation obtains light yellow solid 4 (152mg, 51%).1H NMR (600MHz,CDCl3) δ 7.94 (d, J=9.0Hz, 1H), 7.89-7.84 (m, 2H), 7.79 (d, J=8.4Hz, 1H), 7.77- 7.75 (m, 1H), 7.66 (t, J=8.4Hz, 2H), 7.55 (dd, J=8.2,4.8Hz, 3H), 7.48 (d, J=9.0Hz, 1H), 7.34 (t, J=8.6Hz, 2H), 7.24-7.20 (m, 1H), 7.19-7.13 (m, 3H), 7.07-7.02 (m, 2H), 6.54 (s, 1H), 5.46 (dd, J=44.4,14.4Hz, 2H), 5.20 (dd, J=34.2,12.6Hz, 2H), 4.38 (m, 2H), 2.20 (t, J =2.3Hz, 1H)13C NMR(150MHz,CDCl3)δ153.5,153.0,145.6,133.9,133.9,133.7,133.2, 133.2,131.9,129.7,129.6,129.5,129.0,128.0,127.9,127.8,127.8,127.2,126.8, 126.8,126.4,126.3,125.5,125.4,125.3,124.0,123.9,122.4,120.8,120.4,115.9, 115.6,79.1,75.2,64.3,56.9,54.1。
(5) compound (R) -1- (anthracene -9- ylmethyls) -4- (((2'- ((1- (naphthalene -2- ylmethyls) -1H-1,2,3- triazoles - 4- yls) methoxyl group)-[1,1'- dinaphthalene] -2- bases) epoxide) methyl) -1H-1, the synthesis of 2,3- triazoles 5
Compound 1 (31mg, 0.13mmol) and compound 4 (48mg, 0.09mmol) are dissolved in 10mL tetrahydrofurans (THF) in, sequentially add water (10mL), cupric sulfate pentahydrate (4.3mg, 0.01mmol) and L-AA sodium salt (5.3mg, 0.03mmol), room temperature lucifuge is reacted, and TLC shows that initial feed disappears substantially, and reaction solution is extracted with dichloromethane, collects drying Organic phase, vacuum rotary steam remove solvent, and column chromatography for separation obtains yellow solid 5 (62mg, 90%).1H NMR(400MHz, CDCl3) δ 8.66 (s, 1H), 8.17-8.13 (m, 2H), 8.05 (d, J=8.8Hz, 2H), 7.85 (dd, J=6.6,2.8Hz, 1H), 7.76 (dd, J=8.4Hz, 9.6Hz, 2H), 7.60-7.49 (m, 9H), 7.32 (d, J=8.2Hz, 1H), 7.24 (d, J= 9.0Hz, 1H), 7.17 (d, J=9.0Hz, 1H), 7.15-7.12 (m, 1H), 7.12-7.07 (m, 1H), 6.96 (ddd, J= 10.4,7.4,2.4Hz, 3H), 6.85 (m, 3H), 6.33 (s, 1H), 6.25 (d, J=1.6Hz, 2H), 6.04 (s, 1H), 5.35 (s, 2H), 4.74 (ddd, J=26.6,24.9,12.5Hz, 4H)13C NMR(100MHz,CDCl3)δ153.7,153.3, 145.2,144.8,133.8,133.6,133.3,133.3,131.9,131.6,131.0,129.9,129.6,129.6, 129.3,129.2,129.1,128.1,127.9,127.7,127.7,127.5,126.9,126.3,126.3,125.7, 125.5,125.4,125.0,123.9,123.6,123.1,122.4,121.8,121.1,116.4,115.2,64.5,63.8, 54.2,46.5。
2nd, acquired part of compounds
Series one：
Series two：
Series three：
Series four：
3rd, the fluorescence data analysis of compound Preliminary Determination
This experiment is characterized with ultraviolet and fluorescence to the compound of I, II, III, IV series of all synthesis.As a result show Show, in DMSO-H2Ca is added in O systems2+Fluorescence intensity can be greatly enhanced, particularly compound II-4, III-8, III-4 The fluorescence intensity change and Ca of system2+Concentration is 5 × 10-6-5×10-4It is linear in the range of mol/L, it is possible to achieve DMSO-H2O systems are for Ca2+Quantitative detection.
Embodiment above describes the general principle of the present invention, main features and advantages, the technical staff of the industry should Understand, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and specification Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements are each fallen within In the scope of protection of the invention.

Claims (7)

1. asymmetric double -1,2,3- triazole compounds, it is characterised in that its structural formula is：
Wherein Ar and Ar ' is the combination of following structure and Ar is different from Ar '：
2. the asymmetry double -1 described in a kind of claim 1, the preparation method of 2,3- triazole compounds, it is characterised in that tool Body step is：
The halogenated aromatic compound of (1) two kind of different structure generates the nitrine virtue of two kinds of different structures with reaction of sodium azide respectively Based compound；
(2) 1,1 '-union -2-naphthols react to obtain the dinaphthalene compound of propargyl substitution with propargyl bromide；
(3) the dinaphthalene compound of propargyl substitution and a kind of structure nitrine aryl compound are in SODIUM ASCORBATE and the work of mantoquita After lower reaction, then react and be made not in the presence of SODIUM ASCORBATE and mantoquita with another structure nitrine aryl compound Symmetric double -1,2,3- triazole compounds.
3. according to claim 2 asymmetric double -1, the preparation method of 2,3- triazole compounds, it is characterised in that： The detailed process of step (1) is：The halogenated aromatic compound of two kinds of different structures is added separately in differential responses container simultaneously DMF dissolving is added, Sodium azide is added under stirring state, overnight, TLC monitoring raw materials have reacted for room temperature reaction Entirely, reaction is extracted after terminating with dichloromethane, and organic phase is dried, and vacuum rotary steam removes solvent, and column chromatography for separation obtains two kinds not Isostructural nitrine aryl compound.
4. according to claim 2 asymmetric double -1, the preparation method of 2,3- triazole compounds, it is characterised in that： The detailed process of step (2) is：(R)-(1,1- binaphthalene) -2 is added in reaction vessel, 2 '-glycol is simultaneously dissolved with acetonitrile, then Add potassium carbonate and 3- propargyl bromides and terminate in 85 DEG C of back flow reactions, TLC detection reactions, organic phase is dried, and vacuum rotary steam removes Solvent, column chromatography for separation obtain the dinaphthalene compound of propargyl substitution.
5. according to claim 2 asymmetric double -1, the preparation method of 2,3- triazole compounds, it is characterised in that： The detailed process of step (3) is：The dinaphthalene compound that propargyl substitutes is dissolved in four with a kind of structure nitrine aryl compound In hydrogen furans, water, cupric sulfate pentahydrate and L-AA sodium salt, the reaction of room temperature lucifuge are sequentially added, TLC shows initial feed base This disappearance, reaction solution are extracted with dichloromethane, are collected and are dried organic phase, and vacuum rotary steam removes solvent, and column chromatography for separation obtains mesh Mark compound, then target compound and another structure nitrine aryl compound be dissolved in tetrahydrofuran, sequentially add water, Cupric sulfate pentahydrate and L-AA sodium salt, the reaction of room temperature lucifuge, TLC show that initial feed disappears substantially, reaction solution dichloro Methane extracts, and collects and dries organic phase, and vacuum rotary steam removes solvent, and column chromatography for separation obtains target product asymmetric double -1,2, 3- triazole compounds.
6. the double applications of -1,2,3- triazole compounds in fluorescence chemical sensor of asymmetry described in claim 1.
7. application according to claim 6, it is characterised in that：Double -1,2,3- the triazole compounds of described asymmetry As fluorescence chemical sensor in DMSO-H2Ca is quantitatively detected in O systems2+In application, wherein Ca2+Detectable concentration scope be 5×10-6-5×10-4mol/L。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108863961A (en) * 2018-08-01 2018-11-23 河南师范大学 A kind of triazole anthraquinone derivative silver ion fluorescence probe and its preparation method and application
CN113527267A (en) * 2021-06-21 2021-10-22 山东盛安贝新能源有限公司 C2 symmetric duplex nitrogen heterocyclic ring fluorocarbon surfactant and preparation of aqueous phase micelle thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108863961A (en) * 2018-08-01 2018-11-23 河南师范大学 A kind of triazole anthraquinone derivative silver ion fluorescence probe and its preparation method and application
CN108863961B (en) * 2018-08-01 2021-05-25 河南师范大学 Triazole anthraquinone derivative silver ion fluorescent probe and preparation method and application thereof
CN113527267A (en) * 2021-06-21 2021-10-22 山东盛安贝新能源有限公司 C2 symmetric duplex nitrogen heterocyclic ring fluorocarbon surfactant and preparation of aqueous phase micelle thereof
CN113527267B (en) * 2021-06-21 2022-09-02 山东盛安贝新能源有限公司 C2 symmetric duplex nitrogen heterocyclic ring fluorocarbon surfactant and preparation of aqueous phase micelle thereof

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