CN109336843A - A kind of double benzothiazole compounds and its synthetic method - Google Patents
A kind of double benzothiazole compounds and its synthetic method Download PDFInfo
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- CN109336843A CN109336843A CN201811327651.6A CN201811327651A CN109336843A CN 109336843 A CN109336843 A CN 109336843A CN 201811327651 A CN201811327651 A CN 201811327651A CN 109336843 A CN109336843 A CN 109336843A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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Abstract
The invention proposes a kind of double benzothiazole compounds and its synthetic methods, include the following steps: step 1: the preparation for double benzothiazoles that amino replaces: using benzidine as starting material, in organic solvent, under bromine catalysis, react to obtain double benzothiazoles of amino substitution with potassium rhodanide；Step 2: hydrolysis: double benzothiazoles that amino is replaced are added in alkaline aqueous solution, back hydrolysis, generate thiazole ring open-loop products；Step 3: double benzothiazoles synthesis that aryl replaces: thiazole ring open-loop products are added in organic solvent, under sodium hydrogensulfite catalysis, are reacted with substituted aromatic aldehyde compound, and double benzothiazole compounds are obtained.The present invention is of great significance for developing such compound in the application of material and field of medicaments.
Description
Technical field
The invention belongs to double benzothiazole compound synthesis technical fields, in particular to a kind of double benzothiazoles
Close object and its synthetic method.
Background technique
Cancer is a kind of complex disease for influencing the billions of people in the whole world, is still developing country and prosperity at present
National the first dead big and second largest Etiological.Double benzothiazole compounds have big pi-conjugated system, when by
When the effect or illumination of electric field, theoretically, electronics is excited into the outer layer unoccupied orbital of molecule, in electronics returns to
When layer molecular orbit, the energy of absorption will release in the form of an electromagnetic wave, form distinctive fluorescence phenomenon, because
This this kind of material has great potential using value in luminous organic material field.Many document report benzothiazoles
Compound has apparent anti-tumor activity and other activity (T.D.Bradshaw, E.L.stone, et al., Breast
cancer research and treatment,2008,110:57-68；C.G.Mortimer,G.Wells,et al.,
Journal of medicinal chemistry, 2006,49:179-185), still, the change still is disclosed without document at present
The specific molecular structure and synthetic method for closing object, so that the research for the compound is in the lag phase, it is difficult to obtain essence
Property progress.
Therefore, it in view of above scheme in actual fabrication and in place of implementing using upper missing, and corrected, improved, together
When in line with the spirit and theory asked, and by the knowledge of profession, the auxiliary of experience, and after multi-party clever thought, test, side is created
The present invention is set out, a kind of double benzothiazole compounds and its synthetic method is provided, its structure can be specified, and pass through
Simple method can be prepared, and saved cost, can be prepared target compound by simple method, and make compound
Typical structure definitely, is of great significance for developing such compound in the application of material and field of medicaments.
Summary of the invention
On the one hand, the present invention proposes a kind of double benzothiazole compounds, solves the problems of the prior art.This hair
Bright technical solution is achieved in that double benzothiazole compounds, typical structure are as follows:
As a preferred embodiment, wherein R=H, C1~C10Alkyl, C1~C10Alkoxy, F, Cl, Br,
One or more of I or CN.
On the other hand, the present invention also provides a kind of double benzothiazole compound synthetic methods, include the following steps:
Step 1: the preparation for double benzothiazoles that amino replaces: using benzidine as starting material, in organic solvent,
Under bromine catalysis, react to obtain double benzothiazoles of amino substitution with potassium rhodanide；
Step 2: hydrolysis: double benzothiazoles that amino is replaced are added in alkaline aqueous solution, back hydrolysis, generate thiazole
Ring open-loop products；
Step 3: double benzothiazoles synthesis that aryl replaces: thiazole ring open-loop products being added in organic solvent, in sulfurous
It under sour hydrogen sodium catalysis, is reacted with substituted aromatic aldehyde compound, obtains double benzothiazole compounds.
As a preferred embodiment, the preparation reaction temperature for double benzothiazoles that amino replaces is 0 in step 1
~5 DEG C, reaction dissolvent is glacial acetic acid.
As a preferred embodiment, in step 2, amino replaces in hydrolysis double benzothiazoles and hydrogen-oxygen
The molar ratio for changing potassium is 1:2~3.
As a preferred embodiment, hydrolysate and fragrance in double benzothiazoles synthesis that step 3 aryl replaces
The molar ratio of aldehyde is 1:2~3, and the ratio of solvent and hydrolysate is 10mL~15mL:1.0g.
As a preferred embodiment, step 1 includes, by 50mL glacial acetic acid, 18.42g (0.1mol) benzidine and
14.58g (0.15mol) potassium rhodanide is added in 250mL there-necked flask, is stirred to react under ice bath 1 hour, and in backward reaction solution
14.4g bromine water is slowly added dropwise, continues insulated and stirred and reacts 2h, filtering dries after being washed with methanol, obtains 22.68g yellow solid,
Through mass spectrum and nuclear magnetic resonance determine compound be 6,6'- it is bis- -1,3- benzothiazole 2,2'- diamines,1H NMR (300MHz, DMSO-
d6) δ: 4.05 (s, 4H ,-NH2), 7.74 (d, J=9.0Hz, 2H, Bz-5), 8.26 (d, J=9.0Hz, 2H, Bz-4), 8.32
(s, 2H, Bz-7)
As a preferred embodiment, step 2 includes, by 14.9g (0.05mol) 6,6'- it is bis- -1,3- benzo thiophene
Azoles -2,2'- diamines, 300mL methanol and 5.6g potassium hydroxide are added in there-necked flask, and solution is heated to 80 DEG C and is stirred to react 6h, stops
It only heats, 100mL water is added into reaction solution, filtered after stirring 0.5h, wash filter cake with methanol, 9.5g yellow is obtained after drying
Solid determines that compound is 4,4'-, bis- amido -3,3'- hexichol thiophenol through mass spectrum and nuclear magnetic resonance.1H NMR (300MHz,
DMSO-d6) δ: 3.13 (s, 2H ,-SH), 4.01 (s, 4H ,-NH2), 6.43 (d, J=9.0Hz, 2H, Bz-5), 7.12 (dd, J
=2.4,9.0Hz, 2H, Bz-6), 7.14 (d, J=2.4Hz, 2H, Bz-2).
As a preferred embodiment, step 3 includes by bis- amido -3,3'- hexichol of 2.0g (0.01moL) 4,4'-
Thiophenol, 1.7g (0.02moL) sodium hydrogensulfite, 1.9g (0.02moL) p-tolyl aldehyde and 160mL anhydrous methanol are added three
In mouth bottle, back flow reaction 8h is evaporated reaction solution, and product separates (chloroform: methanol=30:1) with silica gel column chromatography, finally obtains
Compound is bis- [2- (4'- aminomethyl phenyl) -1H- benzothiazole],1H-NMR (300MHz, DMSO-d6) δ: 2.36 (s, 6H), 7.30
(d, 2H), 7.68 (d, 2H), 7.78 (dd, 2H, J=2.4,9.0Hz), 7.82 (d, 2H, J=9.0Hz), 8.36 (d, 2H, J
=2.4).
As a preferred embodiment, step 3 includes, double benzothiazoles chemical combination according to claim 8
Object synthetic method, which is characterized in that step 3 includes, by bis- amido -3,3'- hexichol thiophenol of 2.0g (0.01moL) 4,4'-,
1.7g (0.02moL) sodium hydrogensulfite, 3.0g (0.02moL) p-bromobenzaldehyde and 160mL anhydrous methanol are added in there-necked flask,
Back flow reaction 8h is evaporated reaction solution, and product separates (chloroform: methanol=30:1) with silica gel column chromatography, and it is double to finally obtain compound
[2- (4'- bromophenyl) -1H- benzothiazole],1H-NMR (300MHz, DMSO-d6) δ: 7.67 (d, 4H, J=9.0Hz), 7.79
(dd, 2H, J=2.4,9.0Hz), 7.84 (d, 2H, J=9.0Hz), 7.88 (d, 4H J=9.0Hz), 8.36 (d, 2H, J=
2.4)。
After above-mentioned technical proposal, the beneficial effects of the present invention are: targeted can be prepared by simple method
Object is closed, and makes the typical structure of compound definitely, for developing such compound in the application of material and field of medicaments
It is of great significance.
Detailed description of the invention
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, below will to embodiment or
Attached drawing needed to be used in the description of the prior art is briefly described, it should be apparent that, the accompanying drawings in the following description is only
Some embodiments of the present invention, for those of ordinary skill in the art, without any creative labor,
It is also possible to obtain other drawings based on these drawings.
Fig. 1 is flow diagram of the invention.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts it is all its
His embodiment, shall fall within the protection scope of the present invention.
The present invention proposes a kind of double benzothiazole compounds, solves the problems of the prior art.Technology of the invention
Scheme is achieved in that double benzothiazole compounds, typical structure are as follows:
Wherein R=H, C1~C10Alkyl, C1~C10Alkoxy, one or more of F, Cl, Br, I or CN.
As shown in Figure 1, the present invention is using benzidine as raw material, in organic solvent, under bromine catalysis, with thiocyanic acid
Double benzothiazoles of amino substitution are first prepared in nak response, then through hydrolysis, then with substituted aromatic aldehyde compound
Condensation reaction obtains target compound；Specifically comprise the following steps:
Step 1: the preparation for double benzothiazoles that amino replaces: using benzidine as starting material, in organic solvent,
Under bromine catalysis, react to obtain double benzothiazoles of amino substitution with potassium rhodanide；In step 1, double benzos of amino substitution
The preparation reaction temperature of thiazole is 0~5 DEG C, and reaction dissolvent is glacial acetic acid.
Step 2: hydrolysis: double benzothiazoles that amino is replaced are added in alkaline aqueous solution, back hydrolysis, generate thiazole
Ring open-loop products；In step 2, the molar ratio of amino replaces in hydrolysis double benzothiazoles and potassium hydroxide is 1:2~3.
Step 3: double benzothiazoles synthesis that aryl replaces: thiazole ring open-loop products being added in organic solvent, in sulfurous
It under sour hydrogen sodium catalysis, is reacted with substituted aromatic aldehyde compound, obtains double benzothiazole compounds.Step 3 aryl
The molar ratio of hydrolysate and aromatic aldehyde is 1:2~3, the ratio of solvent and hydrolysate in the double benzothiazoles synthesis replaced
For 10mL~15mL:1.0g.
Based on above-mentioned theory basis, this method is described further in conjunction with specific embodiments:
Embodiment one
The present embodiment includes the following steps:
Step 1:6,6'- be bis- -1,3- benzothiazole 2, the preparation of 2'- diamines
By 50mL glacial acetic acid, 250mL is added in 18.42g (0.1mol) benzidine and 14.58g (0.15mol) potassium rhodanide
It in there-necked flask, is stirred to react under ice bath 1 hour, and 14.4g bromine water is slowly added dropwise in backward reaction solution, it is anti-to continue insulated and stirred
2h is answered, is filtered, is dried after being washed with methanol, obtain 22.68g yellow solid.Determine that compound is 6 through mass spectrum and nuclear magnetic resonance,
6'- is bis- -1,3- benzothiazole 2,2'- diamines.1H NMR (300MHz, DMSO-d6) δ: 4.05 (s, 4H ,-NH2), 7.74 (d, J=
9.0Hz, 2H, Bz-5), 8.26 (d, J=9.0Hz, 2H, Bz-4), 8.32 (s, 2H, Bz-7).
The preparation of bis- amido -3,3'- hexichol thiophenol of step 2:4,4'-
By 14.9g (0.05mol) 6,6'- it is bis- -1,3- benzothiazole -2,2'- diamines, 300mL methanol and 5.6g hydroxide
Potassium is added in there-necked flask, and solution is heated to 80 DEG C and is stirred to react 6h.Stop heating, 100mL water, stirring are added into reaction solution
It is filtered after 0.5h, washs filter cake with methanol, 9.5g yellow solid is obtained after drying.Determine that compound is through mass spectrum and nuclear magnetic resonance
4,4'- bis- amido -3,3'- hexichol thiophenols,1H NMR (300MHz, DMSO-d6) δ: 3.13 (s, 2H ,-SH), 4.01 (s, 4H ,-
NH2), 6.43 (d, J=9.0Hz, 2H, Bz-5), 7.12 (dd, J=2.4,9.0Hz, 2H, Bz-6), 7.14 (d, J=
2.4Hz, 2H, Bz-2).
Step 3: bis- [2- (4'- aminomethyl phenyl) -1H- benzothiazoles] preparation
By bis- amido -3,3'- hexichol thiophenol of 2.0g (0.01moL) 4,4'-, 1.7g (0.02moL) sodium hydrogensulfite,
1.9g (0.02moL) p-tolyl aldehyde and 160mL anhydrous methanol are added in there-necked flask, and back flow reaction 8h is evaporated reaction solution,
Product separates (chloroform: methanol=30:1) with silica gel column chromatography, finally obtains bis- [2- (4'- the aminomethyl phenyl) -1H- benzene of compound
And thiazole],1H-NMR (300MHz, DMSO-d6) δ: 2.36 (s, 6H), 7.30 (d, 2H), 7.68 (d, 2H), 7.78 (dd, 2H, J
=2.4,9.0Hz), 7.82 (d, 2H, J=9.0Hz), 8.36 (d, 2H, J=2.4).
Embodiment two
The present embodiment includes the following steps:
Step 1:6,6'- be bis- -1,3- benzothiazole 2, the preparation of 2'- diamines
By 50mL glacial acetic acid, 250mL is added in 18.42g (0.1mol) benzidine and 14.58g (0.15mol) potassium rhodanide
It in there-necked flask, is stirred to react under ice bath 1 hour, and 14.4g bromine water is slowly added dropwise in backward reaction solution, it is anti-to continue insulated and stirred
2h is answered, is filtered, is dried after being washed with methanol, obtain 22.68g yellow solid.Determine that compound is 6 through mass spectrum and nuclear magnetic resonance,
6'- is bis- -1,3- benzothiazole 2,2'- diamines,1H NMR (300MHz, DMSO-d6) δ: 4.05 (s, 4H ,-NH2), 7.74 (d, J=
9.0Hz, 2H, Bz-5), 8.26 (d, J=9.0Hz, 2H, Bz-4), 8.32 (s, 2H, Bz-7).
The preparation of bis- amido -3,3'- hexichol thiophenol of step 2:4,4'-
By 14.9g (0.05mol) 6,6'- it is bis- -1,3- benzothiazole -2,2'- diamines, 300mL methanol and 5.6g hydroxide
Potassium is added in there-necked flask, and solution is heated to 80 DEG C and is stirred to react 6h.Stop heating, 100mL water, stirring are added into reaction solution
It is filtered after 0.5h, washs filter cake with methanol, 9.5g yellow solid is obtained after drying.Determine that compound is through mass spectrum and nuclear magnetic resonance
4,4'- bis- amido -3,3'- hexichol thiophenols.1H NMR (300MHz, DMSO-d6) δ: 3.13 (s, 2H ,-SH), 4.01 (s, 4H ,-
NH2), 6.43 (d, J=9.0Hz, 2H, Bz-5), 7.12 (dd, J=2.4,9.0Hz, 2H, Bz-6), 7.14 (d, J=
2.4Hz, 2H, Bz-2).
Step 3: bis- [2- (4'- bromophenyl) -1H- benzothiazoles] preparation
Double benzothiazole compound synthetic methods according to claim 8, which is characterized in that step 3 includes,
By bis- amido -3,3'- hexichol thiophenol of 2.0g (0.01moL) 4,4'-, 1.7g (0.02moL) sodium hydrogensulfite, 3.0g
(0.02moL) p-bromobenzaldehyde and 160mL anhydrous methanol are added in there-necked flask, back flow reaction 8h, are evaporated reaction solution, and product is used
Silica gel column chromatography separates (chloroform: methanol=30:1), and it is bis- [2- (4'- bromophenyl) -1H- benzothiazole] to finally obtain compound
,1H-NMR (300MHz, DMSO-d6) δ: 7.67 (d, 4H, J=9.0Hz), 7.79 (dd, 2H, J=2.4,9.0Hz), 7.84 (d,
2H, J=9.0Hz), 7.88 (d, 4H, J=9.0Hz), 8.36 (d, 2H, J=2.4).
This synthetic method by simple 3 step can synthesising target compound so that the typical structure of compound is brighter
Really, it is of great significance for developing such compound in the application of material and field of medicaments.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of double benzothiazole compounds, which is characterized in that its typical structure is as follows:
2. double benzothiazole compounds according to claim 1, which is characterized in that wherein R=H, C1~C10Alkyl,
C1~C10Alkoxy, one or more of F, Cl, Br, I or CN.
3. a kind of double benzothiazole compound synthetic methods, which comprises the steps of:
Step 1: the preparation for double benzothiazoles that amino replaces: using benzidine as starting material, in organic solvent, in bromine
Under catalysis, react to obtain double benzothiazoles of amino substitution with potassium rhodanide；
Step 2: hydrolysis: double benzothiazoles that amino is replaced are added in alkaline aqueous solution, back hydrolysis, generate thiazole ring open loop
Product；
Step 3: double benzothiazoles synthesis that aryl replaces: thiazole ring open-loop products being added in organic solvent, in bisulfite
It under sodium catalysis, is reacted with substituted aromatic aldehyde compound, obtains double benzothiazole compounds.
4. double benzothiazole compound synthetic methods according to claim 3, which is characterized in that in step 1, amino is taken
The preparation reaction temperature of double benzothiazoles in generation is 0~5 DEG C, and reaction dissolvent is glacial acetic acid.
5. double benzothiazole compound synthetic methods according to claim 3, which is characterized in that in step 2, hydrolysis is anti-
The molar ratio of the double benzothiazoles and potassium hydroxide of answering middle amino to replace is 1:2~3.
6. double benzothiazole compound synthetic methods according to claim 3, which is characterized in that step 3 aryl replaces
The synthesis of double benzothiazoles in the molar ratio of hydrolysate and aromatic aldehyde be 1:2~3, the ratio of solvent and hydrolysate is 10mL
~15mL:1.0g.
7. double benzothiazole compound synthetic methods according to claim 4, which is characterized in that step 1 includes inciting somebody to action
50mL glacial acetic acid, 18.42g (0.1mol) benzidine and 14.58g (0.15mol) potassium rhodanide are added in 250mL there-necked flask, ice
It is stirred to react under bath 1 hour, and 14.4g bromine water is slowly added dropwise in backward reaction solution, continued insulated and stirred and react 2h, filter, use
Methanol washing after dry, obtain 22.68g yellow solid, through mass spectrum and nuclear magnetic resonance determine compound be 6,6'- it is bis- -1,3- benzo
Thiazole 2,2'- diamines,1H NMR (300MHz, DMSO-d6) δ: 4.05 (s, 4H ,-NH2), 7.74 (d, J=9.0Hz, 2H, Bz-
5), 8.26 (d, J=9.0Hz, 2H, Bz-4), 8.32 (s, 2H, Bz-7).
8. double benzothiazole compound synthetic methods according to claim 7, which is characterized in that step 2 includes inciting somebody to action
14.9g (0.05mol) 6,6'- is bis--and 1,3- benzothiazole -2,2'- diamines, 300mL methanol and 5.6g potassium hydroxide is added three mouthfuls
In bottle, solution is heated to 80 DEG C and is stirred to react 6h, stops heating, and 100mL water is added into reaction solution, filters after stirring 0.5h,
Filter cake is washed with methanol, 9.5g yellow solid is obtained after drying.Determine that compound is 4,4'-, bis- amido-through mass spectrum and nuclear magnetic resonance
3,3'- hexichol thiophenols.1H NMR (300MHz, DMSO-d6) δ: 3.13 (s, 2H ,-SH), 4.01 (s, 4H ,-NH2), 6.43 (d, J
=9.0Hz, 2H, Bz-5), 7.12 (dd, J=2.4,9.0Hz, 2H, Bz-6), 7.14 (d, J=2.4Hz, 2H, Bz-2).
9. double benzothiazole compound synthetic methods according to claim 8, which is characterized in that step 3 includes inciting somebody to action
Bis- amido -3,3'- hexichol thiophenol of 2.0g (0.01moL) 4,4'-, 1.7g (0.02moL) sodium hydrogensulfite, 1.9g (0.02moL)
P-tolyl aldehyde and 160mL anhydrous methanol are added in there-necked flask, and back flow reaction 8h is evaporated reaction solution, product silicagel column color
Spectrum separation (chloroform: methanol=30:1), it is bis- [2- (4'- aminomethyl phenyl) -1H- benzothiazole] to finally obtain compound,1H-NMR
(300MHz, DMSO-d6) δ: 2.36 (s, 6H), 7.30 (d, 2H), 7.68 (d, 2H), 7.78 (dd, 2H, J=2.4,9.0Hz),
7.82 (d, 2H, J=9.0Hz), 8.36 (d, 2H, J=2.4).
10. double benzothiazole compound synthetic methods according to claim 8, which is characterized in that step 3 includes inciting somebody to action
Bis- amido -3,3'- hexichol thiophenol of 2.0g (0.01moL) 4,4'-, 1.7g (0.02moL) sodium hydrogensulfite, 3.0g (0.02moL)
P-bromobenzaldehyde and 160mL anhydrous methanol are added in there-necked flask, and back flow reaction 8h is evaporated reaction solution, product silica gel column chromatography
It separates (chloroform: methanol=30:1), it is bis- [2- (4'- bromophenyl) -1H- benzothiazole] to finally obtain compound,1H-NMR
(300MHz, DMSO-d6) δ: 7.67 (d, 4H, J=9.0Hz), 7.79 (dd, 2H, J=2.4,9.0Hz), 7.84 (d, 2H, J=
9.0Hz), 7.88 (d, 4H J=9.0Hz), 8.36 (d, 2H, J=2.4).
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| CN111423563A (en) * | 2020-05-25 | 2020-07-17 | 陕西师范大学 | For detecting Fe3+Fused heterocyclic conjugated polymer and preparation method and application thereof |
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| CN1683348A (en) * | 2005-03-17 | 2005-10-19 | 上海交通大学 | Aminobenzothiazole monomer containing alicyclic macro side group and its preparing method |
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| CN111423563A (en) * | 2020-05-25 | 2020-07-17 | 陕西师范大学 | For detecting Fe3+Fused heterocyclic conjugated polymer and preparation method and application thereof |
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Application publication date: 20190215 |