CN110028517A - A kind of one kettle way prepares the synthetic method of nitrogen bromo alkyl spiro-pyrans class compound - Google Patents
A kind of one kettle way prepares the synthetic method of nitrogen bromo alkyl spiro-pyrans class compound Download PDFInfo
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- CN110028517A CN110028517A CN201910463837.2A CN201910463837A CN110028517A CN 110028517 A CN110028517 A CN 110028517A CN 201910463837 A CN201910463837 A CN 201910463837A CN 110028517 A CN110028517 A CN 110028517A
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- inorganic base
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 10
- 238000010189 synthetic method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 10
- 238000010992 reflux Methods 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 238000010898 silica gel chromatography Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 239000000908 ammonium hydroxide Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000005580 one pot reaction Methods 0.000 abstract description 4
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical class C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- 241001141101 Nitrospirales Species 0.000 description 5
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- FDVITFMRUUGIBF-UHFFFAOYSA-N 2-methylidene-1,3-dihydroindole Chemical compound C1=CC=C2NC(=C)CC2=C1 FDVITFMRUUGIBF-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002894 chemical waste Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001338 self-assembly Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- STBMZSJLFYGOJU-UHFFFAOYSA-N 1,1-dibromooctane Chemical compound CCCCCCCC(Br)Br STBMZSJLFYGOJU-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- -1 bromo compound Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses the synthetic methods that a kind of one kettle way prepares nitrogen bromo alkyl spiro-pyrans class compound, belong to organic synthesis field.For the present invention with 2,3,3- trimethyl -3H- indoles, dibromoalkane and 5- nitrosalicylaldehyde for raw material, inorganic base is catalyst, and spiro-pyrans class compound is prepared.The synthetic method craft is simple, one pot of total overall reaction completion, and intermediate product does not need separating-purifying, and reaction process does not need anhydrous and oxygen-free operation, has the advantages that synthesis cost is low using inorganic base.
Description
Technical field
The invention belongs to organic synthesis fields, and in particular to a kind of one kettle way prepares nitrogen bromo alkyl spiro-pyrans class compound
Synthetic method.
Background technique
It is stimulated as a kind of ideal external force, illumination has the advantages that facilitate control and do not generate chemical waste.It is photosensitive
Molecule can realize structural isomerism under light stimulation, can apply as molecular switch in biomedicine field and material neck
Domain.
Spiro-pyrans generates the change of color change and state of charge in photo-isomerisation process.Spiro-pyrans is in illumination
Under the conditions of generate plane and nonplanar structure and change, this kind variation can regulate and control the self-assembly property of spiro-pyrans molecule itself with
And its self-assembly property with other plane class molecules.The state of charge that spiro-pyrans molecule generates in photo-isomerisation process changes
Can influence its with DNA binding property (Journal of the American Chemical Society, 2008,130,
11836–11837).In addition, spiropyran compounds are also important dye molecule.
In numerous spiropyran compounds, the alkyl-substituted 6- nitro spiro-pyrans of nitrogen bromo is most widely used point
One of son.The 6- nitro spiro-pyrans that azanyl replaces needs a point three steps synthesis: one, former for starting with 2,3,3- tri-methyl indole
Material, bromo compound are alkylated nitrogen-atoms；Two, it is obtained among methylene indoline with the indoles of alkali process N-alkylation
Body；Three, methylene indoline intermediate and 5- nitrosalicylaldehyde are condensed to yield the spiropyran compounds (Chemical of needs
Communications,2010,46,7130-7132；The Journal of Organic Chemistry,2010,75,
2752-2755).The methylene indoline intermediate that second step reacts is oxidized easily, and the overall of this kind of route is caused to produce
Rate is lower.In addition to this, the post-processing operation that three-step reaction is related to is relatively more, can generate a large amount of chemical waste.
Summary of the invention
For the problem that above-mentioned spiro-pyrans class compound synthesis step is more and combined coefficient is low, the present invention provides one
The synthetic method of the kind alkyl-substituted 6- nitro spiro-pyrans of one pot process nitrogen bromo.
Technical scheme is as follows:
The nitrogen bromo alkyl spiro-pyrans synthesized in the present invention, it has the following structure formula:
A kind of synthetic method of one pot process nitrogen bromo alkyl spiro-pyrans comprising following steps:
It weighs molar ratio to be dissolved in solvent A for 2,3, the 3- trimethyl -3H- indoles and dibromoalkane of 1:1, the reactant
System is heated to reflux 24 hours under agitation, and reaction system is cooled to room temperature；Weighing inorganic base B respectively, (inorganic base B is to urge
Agent, inorganic base B and 2, the molar ratios of 3,3- trimethyl -3H- indoles are 1:1) and 5- nitrosalicylaldehyde (5- nitrosalicylaldehyde with
The molar ratio of 2,3,3- trimethyl -3H- indoles is 1:1) it is added in above-mentioned reaction system, the reaction system is at room temperature
It is stirred to react 10 minutes, system acid is neutralized, then washing, extraction are concentrated through vacuum distillation, obtain Huang through silica gel column chromatography
Color solid.
Solvent A is any one of methanol, ethyl alcohol, chloroform, acetonitrile or tetrahydrofuran or its mixed solvent, inorganic base B
For any one of ammonium hydroxide, sodium hydroxide or potassium hydroxide.
Experimental program of the invention is compared to the synthetic method of report early period, has the following obvious advantages:
The synthetic route of such spiropyran compounds is reduced to single step reaction by three-step reaction for the first time, does not need anhydrous nothing
Oxygen operation, experimental implementation are simplified；
Oxidation of the methylene indoline intermediate in last handling process is avoided, so that total synthetic yield is improved；
One pot process greatly reduces chemical waste caused by last handling process in synthesis process.
Specific embodiment
Technical solution in order to preferably explain the present invention embodies the present invention on synthesis azanyl spiro-pyrans class compound
The advantages of, explanation is further explained by embodiment below:
Embodiment 1:1'- bromopropyl -3', 3'- dimethyl -6- nitro spiral shell [chromene -2,2'- indoline]
The flask of a 50mL is taken, reflux condensate device is installed, 2.0mL (12.56mmol) 2,3,3- trimethyl-is added
3H- indoles, 1.27mL 1, the methanol of 3- dibromopropane (12.56mmol) and 20mL are heated to reflux 24 hours；Stop heating,
Reaction system is allowed to be cooled to room temperature；The ammonium hydroxide and 2.1g of 1.79mL (12.56mmol) 26-28% are sequentially added into above-mentioned system
(12.56mmol) 5- nitrosalicylaldehyde is further continued for reaction 10 minutes, and system acid is neutralized, and washing, extraction are spin-dried for solvent, use
Silica gel column chromatography (eluant, eluent is petrol ether/ethyl acetate) obtains yellow solid 1.46g, yield 27% to purification of products.
1H NMR(400MHz,CDCl3)δ1.19(s,3H),1.28(s,3H),2.00-2.13(m,1H),2.20-2.32
(m, 1H), 3.24-3.33 (m, 1H), 3.35-3.48 (m, 3H), 5.87 (d, J=10.4Hz, 1H), 6.64 (d, J=7.6Hz,
1H), 6.75 (d, J=8.8Hz, 1H), 6.90 (t, J=7.4Hz, 1H), 6.93 (d, J=10.4Hz, 1H), 7.10 (d, J=
7.2Hz, 1H), 7.20 (dt, J=7.6Hz, 1.2Hz, 1H), 8.01 (d, J=2.8Hz, 1H), 8.02 (dd, J=8.4Hz,
2.8Hz,1H).
Embodiment 2:1'- brombutyl -3', 3'- dimethyl -6- nitro spiral shell [chromene -2,2'- indoline]
The flask of a 50mL is taken, reflux condensate device is installed, 2.0mL (12.56mmol) 2,3,3- trimethyl-is added
The ethyl alcohol of 3H- indoles, 1.50mL Isosorbide-5-Nitrae-dibromobutane (12.56mmol) and 20mL, is heated to reflux 24 hours；Stop heating,
Reaction system is allowed to be cooled to room temperature；The ammonium hydroxide and 2.1g of 1.79mL (12.56mmol) 26-28% are sequentially added into above-mentioned system
(12.56mmol) 5- nitrosalicylaldehyde is further continued for reaction 10 minutes, and system acid is neutralized, and washing, extraction are spin-dried for solvent, use
Silica gel column chromatography (eluant, eluent is petrol ether/ethyl acetate) obtains yellow solid 1.89g, yield 34% to purification of products.
1H NMR(500MHz,CDCl3)δ1.19(s,3H),1.29(s,3H),1.73-1.93(m,4H),3.14-3.25
(m, 2H), 3.35-3.42 (m, 2H), 5.87 (d, J=10.0Hz, 1H), 6.59 (d, J=7.5Hz, 1H), 6.75 (d, J=
8.5Hz, 1H), 6.89 (t, J=15.0Hz, 1H), 6.92 (d, J=10.5Hz, 1H), 7.10 (d, J=7.0Hz, 1H), 7.20
(t, J=15.0Hz, 1H), 8.00-8.03 (m, 2H)
Embodiment 3:1'- bromine amyl -3', 3'- dimethyl -6- nitro spiral shell [chromene -2,2'- indoline]
The flask of a 50mL is taken, reflux condensate device is installed, 2.0mL (12.56mmol) 2,3,3- trimethyl-is added
3H- indoles, 1.71mL 1, the chloroform of pentamethylene bromide (12.56mmol) and 20mL are heated to reflux 24 hours；Stop heating,
Reaction system is allowed to be cooled to room temperature；The ammonium hydroxide and 2.1g of 1.79mL (12.56mmol) 26-28% are sequentially added into above-mentioned system
(12.56mmol) 5- nitrosalicylaldehyde is further continued for reaction 10 minutes, and system acid is neutralized, and washing, extraction are spin-dried for solvent, use
Silica gel column chromatography (eluant, eluent is petrol ether/ethyl acetate) obtains yellow solid 1.84g, yield 32% to purification of products.
1H NMR(500MHz,CDCl3)δ1.22(s,3H),1.32(s,3H),1.44-1.56(m,2H),1.59-1.66
(m,1H),1.69-1.76(m,1H),1.85-1.92(m,2H),3.16-3.27(m,2H),3.39-3.45(m,2H),5.92
(d, J=10.5Hz, 1H), 6.60 (d, J=7.5Hz, 1H), 6.74 (d, J=8.5Hz, 1H), 6.89 (t, J=15.0Hz,
1H), 6.95 (d, J=10.0Hz, 1H), 7.12 (d, J=7.0Hz, 1H), 7.21 (t, J=15.5Hz, 1H), 8.00-8.03
(m,2H).
Embodiment 4:1'- bromine octyl -3', 3'- dimethyl -6- nitro spiral shell [chromene -2,2'- indoline]
The flask of a 50mL is taken, reflux condensate device is installed, 2.0mL (12.56mmol) 2,3,3- trimethyl-is added
3H- indoles, 2.31mL 1, the acetonitrile of bis- bromooctane of 8- (12.56mmol) and 20mL are heated to reflux 24 hours；Stop heating,
Reaction system is allowed to be cooled to room temperature；The sodium hydroxide and 2.1g of 502.4mg (12.56mmol) are sequentially added into above-mentioned system
(12.56mmol) 5- nitrosalicylaldehyde is further continued for reaction 10 minutes, and system acid is neutralized, and washing, extraction are spin-dried for solvent, use
Silica gel column chromatography (eluant, eluent is petrol ether/ethyl acetate) obtains yellow solid 1.94g, yield 31% to purification of products.
1H NMR(500MHz,CDCl3)δ1.18(s,3H),1.28(s,10H),1.39-1.43(m,2H),1.60(dd,J
=44.5Hz, 42.0Hz, 2H), 1.80-1.86 (m, 2H), 3.09-3.20 (m, 2H), 3.39 (t, J=13.5Hz, 2H), 5.86
(d, J=10.5Hz, 1H), 6.57 (d, J=8.0Hz, 1H), 6.74 (d, J=8.5Hz, 1H), 6.85-6.91 (m, 2H), 7.09
(d, J=7.0Hz, 1H), 7.19 (t, J=15.5Hz, 1H), 8.00-8.02 (m, 2H)
Embodiment 5:1'- bromine nonyl -3', 3'- dimethyl -6- nitro spiral shell [chromene -2,2'- indoline]
The flask of a 50mL is taken, reflux condensate device is installed, 2.0mL (12.56mmol) 2,3,3- trimethyl-is added
3H- indoles, 2.55mL 1, the tetrahydrofuran of 9- dibromo nonane (12.56mmol) and 20mL are heated to reflux 24 hours；Stop
Heating, allows reaction system to be cooled to room temperature；Sequentially added into above-mentioned system 704.7mg (12.56mmol) potassium hydroxide and
2.1g (12.56mmol) 5- nitrosalicylaldehyde is further continued for reaction 10 minutes, and system acid is neutralized, and washing, extraction are spin-dried for molten
Agent obtains yellow solid 1.93g, yield 30% with silica gel column chromatography (eluant, eluent is petrol ether/ethyl acetate) to purification of products.
1H NMR(500MHz,CDCl3)δ1.19(s,3H),1.27-1.35(m,11H),1.29-1.41(m,2H),1.55-
1.64 (m, 2H), 1.81-1.87 (m, 2H), 3.10-3.21 (m, 2H), 3.36-3.43 (m, 2H), 5.87 (d, J=10.5Hz,
1H), 6.58 (d, J=7.5Hz, 1H), 6.74 (d, J=8.5Hz, 1H), 6.85-6.92 (m, 2H), 7.09 (d, J=7.0Hz,
1H), 7.19 (t, J=7.5Hz, 1H), 8.00-8.03 (m, 2H)
Claims (2)
1. a kind of one kettle way prepares the synthetic method of nitrogen bromo alkyl spiro-pyrans class compound (its structural formula is shown in formula I),
It is characterized by: it the following steps are included:
It weighs molar ratio to be dissolved in solvent A for 2,3, the 3- trimethyl -3H- indoles and dibromoalkane of 1:1, which exists
It is heated to reflux under stirring condition 24 hours, reaction system is cooled to room temperature；Weighing inorganic base B respectively, (inorganic base B is catalysis
Agent, inorganic base B and 2, the molar ratio of 3,3- trimethyl -3H- indoles are 1:1) and 5- nitrosalicylaldehyde (5- nitrosalicylaldehyde and 2,
The molar ratio of 3,3- trimethyl -3H- indoles is 1:1) it is added in above-mentioned reaction system, which stirs at room temperature
Reaction 10 minutes is mixed, system acid is neutralized, then washing, extraction are concentrated through vacuum distillation, obtain yellow through silica gel column chromatography
Solid.
2. a kind of one kettle way according to claim 1 prepares the synthetic method of nitrogen bromo alkyl spiro-pyrans class compound,
Be characterized in that: solvent A is any one of methanol, ethyl alcohol, chloroform, acetonitrile or tetrahydrofuran or its mixed solvent, inorganic base B
For any one of ammonium hydroxide, sodium hydroxide or potassium hydroxide.
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2019
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Non-Patent Citations (3)
| Title |
|---|
| KAISER, CHRISTOPH，等: "Thermal, Photochromic and Dynamic Properties of Water-Soluble Spiropyrans", 《CHEMISTRYSELECT》 * |
| YILE NIU，等: "Spiropyran-decorated light-responsive amphiphilic poly(a-hydroxy acids) micelles constructed via a CuAAC reaction", 《RSC ADVANCES》 * |
| 薛永强: "《现代有机合成方法与技术》", 31 May 2003 * |
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