CN104761600B - Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrahydroxy-D-glucopyranose bromide - Google Patents
Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrahydroxy-D-glucopyranose bromide Download PDFInfo
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
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Abstract
The invention relates to synthesis and uses of beta-1-imidazole-2,3,4,6-tetrahydroxy-D-glucopyranose bromide and belongs to glucopyranose chemical synthesis by multi-component reactions and uses of the glucopyranose. The synthesis includes: 1) subjecting glucose 1 that is adopted as a raw material to acetylation to obtain a compound 2; 2) performing bromination by adopting the compound 2 as a raw material to obtain a compound 3; 3) reacting the compound 3 with 1-methylimidazole to obtain a compound 4; and 4) hydrolyzing the compound 4 under alkaline conditions to obtain a target compound 5 that is the beta-1-imidazole-2,3,4,6-tetrahydroxy-D-glucopyranose bromide. Ketone-ketone cross Aldol reactions of isatin and derivatives thereof and low-activity ketones are catalyzed by adopting the target compound 5 as an efficient catalyst to synthesize a series of 3-alkyl-3-hydroxy-2-ketone derivatives with potential medicinal value. The synthesis and the uses are advantageous in that: the low-activity ketones which cannot be catalyzed by other catalysts can react directly, thus broadening the range of reaction substrates, a method and operation are simple, reaction time is short, and the yield is high. Reactions are green, economical and efficient.
Description
Technical field
The present invention relates to a kind of many component reactive chemistry synthesizing pyran glucose and application thereof, particularly a kind of bromo β -1-
The synthesis of imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses and purposes.
Background technology
It is most important a kind of C-C bond formeds reaction in modern organic synthesis that Aldol reactions are aldol reaction.Mesh
Before, aldehyde-aldehyde for being carried out by enamine intermediates, aldehyde -one Aldol are reacted to a big pillar of modern organic synthesis chemistry.So
And, due to not activated ketone α-H activity it is relatively low, it is difficult to there is intermolecular ketone -one cross-aldol condensation, therefore, point
Ketone -one cross-aldol condensation is a vitochemical significant challenge between son, and relevant report is considerably less.Want by efficient
Intermolecular ketone -one cross-aldol condensation obtain with potential medical value 3- alkyl -3- hydroxyl -2- ketone derivatives,
Must high, the selectively strong new catalyst of synthesis catalytic activity.
D-Glucose as being distributed widest natural monosaccharide in nature, for it understanding and effect already by people
It is known.But its research in terms of chemical synthesis as monose never causes enough attention.Glucose is used as polysaccharide
Basic structural unit, not only cheap, aboundresources, itself small-molecular-weight, recyclability and water solubility are all caused
Glucose is seen as preparing the desirable feedstock of organic micromolecule catalyst.
Nitrogen heterocyclic ring Cabbeen has special space and electronic structure, is a class bipolarity isoelectronic species, as catalyst,
Its avtive spot is more, and catalysis activity is high.
The combination of sugar and N-heterocyclic carbine has the advantage of Cabbeen and sugar concurrently containing sugared N-heterocyclic carbine, both has to organic reaction
There is higher catalytic activity, there is stronger surface-active again, the solubility of organic compound can be improved, it is great in organic catalysis field
Development volue.
The content of the invention
The invention aims to provide a kind of containing sugared N-heterocyclic carbine bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D-
The synthesis of glucopyranose and purposes, the intermolecular ketone -one cross-aldol condensation of solution is difficult to be occurred, and is difficult to obtain to have and is dived
In the problem of the 3- alkyl -3- hydroxyl -2- ketone derivatives of medical value.
The object of the present invention is achieved like this：The conjunction of bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses
Into, including：1) acetylation is carried out as raw material with glucose 1 and obtains compound 2；2) chemical combination is obtained by raw material Jing bromos of compound 2
Thing 3；3) compound 3 and the reaction of N-methyl imidazoles are obtained into compound 4；4) compound 4 is hydrolyzed in the basic conditions and obtains mesh
Mark compound 5, i.e. bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses are comprised the following steps that：
1) acetylation is carried out as raw material with glucose 1 and generates compound 2, described compound 2 is 1,2,3,4,6- five-second
Acyl group-glucopyranose, its reaction equation is as follows：
Sequentially add in the neck round-bottom flasks of 500mL two DEXTROSE ANHYDROUS of 5.0mmol, the acetic anhydride of 50.0mmol and
30min is stirred in the silicon sulfonic acid SSA of 0.08g, argon gas protection under room temperature, reaction is complete, directly carries out next step reaction；
2) compound 3 is obtained by raw material Jing bromos of compound 2, described compound 3 is bromo- 2,3,4, the 6- tetra--acetyl of 1-
Base glucopyranose, its reaction equation is as follows：
Under argon gas protection ice bath, the glacial acetic acid of 20mL is added in system, be passed through brand-new bromination hydrogen, gas is passed through 1h
React complete afterwards, the product in system is poured in frozen water, extracted with dichloromethane, organic phase saturated sodium thiosulfate solution
Washing, point liquid, organic phase saturated sodium bicarbonate solution is washed to neutrality, is washed with water 2-3 time, separates organic phase, organic phase
With anhydrous sodium sulfate drying, drier is filtered, decompression is spin-dried for obtaining colorless viscous shape liquid, uses VEther:VPetroleum ether=1:1 recrystallization, obtains
Compound 3；
3) compound 3 and N-methyl imidazoles reaction obtains compound 4, and described compound 4 is bromo β -1- imidazoles -2, and 3,
4,6- tetra-acetylated-D- glucopyranoses, its reaction equation is as follows：
The N- methylimidazoles of the compound 3 of 10mmol and 20mmol are placed in 50mL round-bottomed flasks, 1mL acetonitriles are added,
2h is stirred at room temperature, thick white shape solid is obtained, is washed with acetone, suction filtration obtains compound as white solid 4；
4) compound 4 is hydrolyzed in the basic conditions and obtains target product i.e. compound 5, described compound 5 is bromo
β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses, its reaction equation is as follows：
The compound 4 of 2mmol is placed in the neck bottles of 50mL two, under argon gas protection 10mL absolute methanols and 10mL are sequentially added
Anhydrous tetrahydro furan, adds 0.5mmol Anhydrous potassium carbonates after stirring；React under room temperature ar gas environment to terminating, course of reaction by
Thin-layer chromatography (TLC) tracing detection；Suction filtration obtains light yellow liquid, and decompression boils off excess of solvent, obtains pale yellow oily liquid chemical combination
Thing 5；Yellow oil；IR(KBr)ν:3364,3152,1420,1364,1310,1177,1101,1074,1020cm-1；1H
NMR(400MHz,DMSO-d6)(δ,ppm):3.15 (s, 1H), 3.25 (t, J=8.9Hz, 2H), 3.37 (t, J=8.8Hz,
2H), 3.42-3.51 (m, 4H), 3.71 (d, J=10.8Hz, 1H), 3.90 (s, 3H), 5.40 (d, J=8.8Hz, 1H), 7.79
(d, J=1.8Hz, 1H), 7.92 (d, J=1.9Hz, 1H), 9.45 (s, 1H)；13C NMR(100MHz,DMSO-d6):δ136.2,
123.6,120.8,87.0,80.1,76.1,72.8,69.1,60.5,36.0；HRMS(ESI)m/z:calc.for C10H17N2O5
[M-Br]+found(expected):245.1178(245.1132).
The ketone -one of the described catalysis of target product 5 intersects Aldol reaction expressions：
R in compound 8 in formula1Group includes H, 5-F, 5-Cl, 5-Br, 5-CH3, 5-CH3O, 5,7- (CH3)2, 5-NO2；
R1Group includes-C6H5,-CH3；
By [Bmim-G '] of the Isatine derivatives 6,20mol% of 0.1mmol+[Br]-In being placed in 50mL round-bottomed flasks, add
Stir 10 minutes at 50 DEG C of 2mL ethanol, carbonyls 7 is added in system, described compound 7 is 3.0mmol acetophenones
Or 8.0mmol acetone, continuing to stir to reacting complete, course of reaction is by thin-layer chromatography (TLC) tracing detection；Decompression boils off system
Middle excess of solvent, crude product passes through column chromatography (VPetroleum ether:VEthyl acetate=4:1-1:2.5 gradient elutions) obtain purified product 8.
Bromo β -1- imidazoles -2, the purposes of 3,4,6- tetrahydroxy-D- glucopyranoses, by bromo β -1- imidazoles -2,3,4,
6- tetrahydroxy-D- glucopyranoses intersect as catalyst, the ketone -one that catalysis isatin and its derivative are participated in low activity ketone
Aldol reacts, serial 3- alkyl -3- hydroxyl -2- ketone derivatives of the synthesis with potential medical value.
Beneficial effect and advantage：The synthesis of the bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses of the present invention
Method is, containing sugared N-heterocyclic carbine bromo β -1- imidazoles -2, the synthetic method of 3,4,6- tetrahydroxy-D- glucopyranoses, to be made
The ketone -one that isatin and its derivative participate in low activity ketone being successfully catalyzed for catalyst and having intersected Aldol reactions, having synthesized one has been
3- alkyl -3- hydroxyl -2- ketone derivatives of the row with potential medical value.
1st, the reaction is had containing sugared N-heterocyclic carbine bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses
Well catalysis activity, quickly can in high yield obtain product 8, and described product 8 is derivative for 3- alkyl -3- hydroxyl -2- ketone
Thing.
2nd, the yield of reaction is universal higher, shows the universality of substrate.
3rd, not activated low activity ketone can obtain product with higher yields, show the high catalytic activity of the catalyst.
4th, reaction condition is gentle, and simple to operate, the reaction time is especially short, and yield is high, and post processing is easy.
5th, environmental protection, economical and efficient, with high actual application value are reacted.
Specific embodiment
Bromo β -1- imidazoles -2, the synthesis of 3,4,6- tetrahydroxy-D- glucopyranoses, including：1) with glucose 1 as raw material
Carry out acetylation and obtain compound 2；2) compound 3 is obtained by raw material Jing bromos of compound 2；3) by compound 3 and N-methyl miaow
Azoles reaction obtains compound 4；4) in the basic conditions by compound 4 hydrolysis obtain target compound 5, i.e. bromo β -1- imidazoles -
2,3,4,6- tetrahydroxy-D- glucopyranoses, comprise the following steps that：
1) acetylation is carried out as raw material with glucose 1 and generates compound 2, described compound 2 is 1,2,3,4,6- five-second
Acyl group-glucopyranose, its reaction equation is as follows：
Sequentially add in the neck round-bottom flasks of 500mL two DEXTROSE ANHYDROUS of 5.0mmol, the acetic anhydride of 50.0mmol and
30min is stirred in the silicon sulfonic acid SSA of 0.08g, argon gas protection under room temperature, reaction is complete, directly carries out next step reaction；
2) compound 3 is obtained by raw material Jing bromos of compound 2, described compound 3 is bromo- 2,3,4, the 6- tetra--acetyl of 1-
Base glucopyranose, its reaction equation is as follows：
Under argon gas protection ice bath, the glacial acetic acid of 20mL is added in system, be passed through brand-new bromination hydrogen, gas is passed through 1h
React complete afterwards, the product in system is poured in frozen water, extracted with dichloromethane, organic phase saturated sodium thiosulfate solution
Washing, point liquid, organic phase saturated sodium bicarbonate solution is washed to neutrality, is washed with water 2-3 time, separates organic phase, organic phase
With anhydrous sodium sulfate drying, drier is filtered, decompression is spin-dried for obtaining colorless viscous shape liquid, uses VEther:VPetroleum ether=1:1 recrystallization, obtains
Compound 3；
3) compound 3 and N-methyl imidazoles reaction obtains compound 4, and described compound 4 is bromo β -1- imidazoles -2, and 3,
4,6- tetra-acetylated-D- glucopyranoses, its reaction equation is as follows：
The N- methylimidazoles of the compound 3 of 10mmol and 20mmol are placed in 50mL round-bottomed flasks, 1mL acetonitriles are added,
2h is stirred at room temperature, thick white shape solid is obtained, is washed with acetone, suction filtration obtains compound as white solid 4；
4) compound 4 is hydrolyzed in the basic conditions and obtains target product i.e. compound 5, described compound 5 is bromo
β -1- imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses, its reaction equation is as follows：
The compound 4 of 2mmol is placed in the neck bottles of 50mL two, under argon gas protection 10mL absolute methanols and 10mL are sequentially added
Anhydrous tetrahydro furan, adds 0.5mmol Anhydrous potassium carbonates after stirring；React under room temperature ar gas environment to terminating, course of reaction by
Thin-layer chromatography (TLC) tracing detection；Suction filtration obtains light yellow liquid, and decompression boils off excess of solvent, obtains pale yellow oily liquid chemical combination
Thing 5；Yellow oil；IR(KBr)ν:3364,3152,1420,1364,1310,1177,1101,1074,1020cm-1；1H
NMR(400MHz,DMSO-d6)(δ,ppm):3.15 (s, 1H), 3.25 (t, J=8.9Hz, 2H), 3.37 (t, J=8.8Hz,
2H), 3.42-3.51 (m, 4H), 3.71 (d, J=10.8Hz, 1H), 3.90 (s, 3H), 5.40 (d, J=8.8Hz, 1H), 7.79
(d, J=1.8Hz, 1H), 7.92 (d, J=1.9Hz, 1H), 9.45 (s, 1H)；13C NMR(100MHz,DMSO-d6):δ136.2,
123.6,120.8,87.0,80.1,76.1,72.8,69.1,60.5,36.0；HRMS(ESI)m/z:calc.for C10H17N2O5
[M-Br]+found(expected):245.1178(245.1132).
The ketone -one of the described catalysis of target product 5 intersects Aldol reaction expressions：
R in compound 8 in formula1Group includes H, 5-F, 5-Cl, 5-Br, 5-CH3, 5-CH3O, 5,7- (CH3)2,
5-NO2；R1Group includes-C6H5,-CH3；
By [Bmim-G '] of the Isatine derivatives 6,20mol% of 0.1mmol+[Br]-In being placed in 50mL round-bottomed flasks, add
Stir 10 minutes at 50 DEG C of 2mL ethanol, carbonyls 7 is added in system, described compound 7 is 3.0mmol acetophenones
Or 8.0mmol acetone, continuing to stir to reacting complete, course of reaction is by thin-layer chromatography (TLC) tracing detection；Decompression boils off system
Middle excess of solvent, crude product passes through column chromatography (VPetroleum ether:VEthyl acetate=4:1-1:2.5 gradient elutions) obtain purified product 8.
The synthesis of the product 8 of table 1.
Bromo β -1- imidazoles -2, the purposes of 3,4,6- tetrahydroxy-D- glucopyranoses, by bromo β -1- imidazoles -2,3,4,
6- tetrahydroxy-D- glucopyranoses intersect as catalyst, the ketone -one that catalysis isatin and its derivative are participated in low activity ketone
Aldol reacts, serial 3- alkyl -3- hydroxyl -2- ketone derivatives of the synthesis with potential medical value.
Embodiment 1：By taking 3- hydroxyl -3- (2- oxo -2- phenylethyls) indol-2-one (8a) as an example:
Isatin 6a (0.1mmol), target product 5 (20mol%) are placed in 50mL round-bottomed flasks, add 2mL ethanol in
Stir 10 minutes at 50 DEG C, acetophenone (3.0mmol acetophenones or 8.0mmol acetone) is added in system, continue to stir to anti-
Should completely (TLC tracking), decompression boils off excess of solvent in system, and crude product passes through column chromatography (VPetroleum ether:VEthyl acetate=4:1-1:2.5
Gradient elution) obtain sterling 8a.
(brs, 1H), 6.79-6.87 (m, 2H), 7.14-7.18 (m, 1H), 7.26 (d, J=7.6Hz, 1H), 7.49 (t, J
=8.0Hz, 2H), 7.60-7.64 (m, 1H), 7.87-7.89 (m, 2H), 10.26 (br s, 1H)；13C NMR(100MHz,
DMSO-d6):δ196.4,178.3,142.9,136.1,133.4,131.7,128.9,128.7,127.9,123.6,121.1,
109.4,72.9,45.7.HRMS(ESI)m/z:calc.for C16H12NO3[M-H]-:266.0817；found:266.0790.
Claims (3)
1. a kind of bromo β -1- imidazoles -2, the synthesis of 3,4,6- tetrahydroxy-D- glucopyranoses, is characterized in that：Bromo β -1- miaows
Azoles -2, the synthesis of 3,4,6- tetrahydroxy-D- glucopyranoses, including：1) acetylation is carried out as raw material with glucose 1 and obtains chemical combination
Thing 2；2) compound 3 is obtained by raw material Jing bromos of compound 2；3) compound 3 and the reaction of N-methyl imidazoles are obtained into compound 4；
4) compound 4 is hydrolyzed in the basic conditions and obtains target compound 5, i.e. bromo β -1- imidazoles -2,3,4,6- tetrahydroxy-D- pyrroles
Glucopyranoside, comprises the following steps that：
1) acetylation is carried out as raw material with glucose 1 and generates compound 2, described compound 2 is 1,2,3,4,6- five-acetyl
Base-glucopyranose, its reaction equation is as follows：
The DEXTROSE ANHYDROUS of 5.0mmol, the acetic anhydride of 50.0mmol and 0.08g are sequentially added in the neck round-bottom flasks of 500mL two
Silicon sulfonic acid SSA, argon gas protection stirs 30min under room temperature, reaction is complete, directly carries out next step reaction；
2) compound 3 is obtained by raw material Jing bromos of compound 2, described compound 3 is bromo- 2,3,4, the 6- tetra--acetyl group pyrroles of 1-
Glucopyranoside, its reaction equation is as follows：
Under argon gas protection ice bath, the glacial acetic acid of 20mL is added in system, be passed through brand-new bromination hydrogen, gas is passed through after 1h instead
Should be complete, the product in system is poured in frozen water, extracted with dichloromethane, organic phase saturated sodium thiosulfate solution is washed
Wash, point liquid, organic phase saturated sodium bicarbonate solution is washed to neutrality, is washed with water 2-3 time, separate organic phase, organic phase is used
Anhydrous sodium sulfate drying, filters drier, and decompression is spin-dried for obtaining colorless viscous shape liquid, uses VEther:VPetroleum ether=1:1 recrystallization, must change
Compound 3；
3) compound 3 and N-methyl imidazoles reaction obtains compound 4, and described compound 4 is bromo β -1- imidazoles -2, and 3,4,6-
Tetra-acetylated-D- glucopyranoses, its reaction equation is as follows：
The N- methylimidazoles of the compound 3 of 10mmol and 20mmol are placed in 50mL round-bottomed flasks, 1mL acetonitriles are added, in room
The lower stirring 2h of temperature, obtains thick white shape solid, is washed with acetone, and suction filtration obtains compound as white solid 4；
4) compound 4 is hydrolyzed in the basic conditions and obtains target product i.e. compound 5, described compound 5 is bromo β -1-
Imidazoles -2,3,4,6- tetrahydroxy-D- glucopyranoses, its reaction equation is as follows：
The compound 4 of 2mmol is placed in the neck bottles of 50mL two, 10mL absolute methanols is sequentially added under argon gas protection and 10mL is anhydrous
Tetrahydrofuran, adds 0.5mmol Anhydrous potassium carbonates after stirring；React under room temperature ar gas environment to terminating, course of reaction is by thin layer
Chromatography (TLC) tracing detection；Suction filtration obtains light yellow liquid, and decompression boils off excess of solvent, obtains pale yellow oily liquid compound 5.
2. bromo β -1- imidazoles -2 according to claim 1, the synthesis of 3,4,6- tetrahydroxy-D- glucopyranoses, it is special
Levying is：The ketone -one of the described catalysis of target product 5 intersects Aldol reaction expressions：
R in compound 8 in formula1Group includes H, 5-F, 5-Cl, 5-Br, 5-CH3, 5-CH3O, 5,7- (CH3)2, 5-NO2；R2Take
Dai Ji includes-C6H5,-CH3；
By [Bmim-G '] of the Isatine derivatives 6,20mol% of 0.1mmol+[Br]-In being placed in 50mL round-bottomed flasks, 2mL is added
Stir 10 minutes at 50 DEG C of ethanol, add carbonyls 7 in system, described compound 7 be 3.0mmol acetophenones or
8.0mmol acetone, continues to stir to reacting complete, and course of reaction is by thin-layer chromatography (TLC) tracing detection；Decompression is boiled off in system
Excess of solvent, crude product obtains purified product 8 by column chromatography, and described column chromatography is：VPetroleum ether:VEthyl acetate=4:1-1:2.5 gradient
Drip washing.
3. bromo β -1- imidazoles -2 that a kind of claim 1 synthesizes, the purposes of 3,4,6- tetrahydroxy-D- glucopyranoses, it is special
Levying is：Bromo β -1- imidazoles -2, the purposes of 3,4,6- tetrahydroxy-D- glucopyranoses, by bromo β -1- imidazoles -2,3,4,6- tetra-
Hydroxyl-D- glucopyranoses intersect Aldol as catalyst, the ketone -one that catalysis isatin and its derivative are participated in low activity ketone
Reaction, serial 3- alkyl -3- hydroxyl -2- ketone derivatives of the synthesis with potential medical value.
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| CN102617657A (en) * | 2012-02-22 | 2012-08-01 | 徐州师范大学 | Method and reaction device for synthesizing 1-bromo-2,3,4,6-tetra-acetyl glucopyranose |
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| CN102617657A (en) * | 2012-02-22 | 2012-08-01 | 徐州师范大学 | Method and reaction device for synthesizing 1-bromo-2,3,4,6-tetra-acetyl glucopyranose |
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| Carbohydrate-containing N-heterocyclic carbene complexes.;Friederike Tewes, et al.,;《Journal of Organometallic Chemistry》;20070508;第692卷;第4593–4602页. * |
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| Sugar-Incorporated N-Heterocyclic Carbene Complexes.;Takanori Nishioka, et al.,;《Organometallics》;20070130;第26卷;第1126-1128页. * |
| 手性NHC中间体1-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基)咪唑的合成及核磁共振研究.;杨志才等，;《化工中间体》;20131231(第02期);第22-26页. * |
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