CN108178764A - Furans simultaneously [2,3-b] pyridine compounds and their and the synthetic method without metal catalytic - Google Patents
Furans simultaneously [2,3-b] pyridine compounds and their and the synthetic method without metal catalytic Download PDFInfo
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- CN108178764A CN108178764A CN201810017929.3A CN201810017929A CN108178764A CN 108178764 A CN108178764 A CN 108178764A CN 201810017929 A CN201810017929 A CN 201810017929A CN 108178764 A CN108178764 A CN 108178764A
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- GAAHWLQGZIYKLY-UHFFFAOYSA-N CCc1c(C)[o]c2ncccc12 Chemical compound CCc1c(C)[o]c2ncccc12 GAAHWLQGZIYKLY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
Abstract
The present invention relates to a kind of furans simultaneously [2,3 b] pyridine compounds and their and synthetic method without metal catalytic, specifically using the pyridine nitric oxide of 3 substitutions as raw material, acetic anhydride is solvent, and potassium carbonate is alkali, under heating condition, furans simultaneously [2,3 b] pyridine compounds and their is obtained by the reaction.This method has the advantages that easy to operate, reagent is cheap and easily-available, and reaction selectivity is high, and substrate applicability is wide.The present invention has obtained a series of furans simultaneously [2,3 b] pyridine compounds and their with this method for the first time, has broad prospects in terms of the synthesis application for establishing such compound library.
Description
Technical field
The invention belongs to noval chemical compound synthesis and medicinal application fields, are related to furans simultaneously [2,3-b] pyridine compounds and their
Synthetic method and its application in terms of water solubility is improved.
Technical background
Benzofuran compounds are a kind of important naturally occurring heterocyclic compounds, they are due to having extensive life
Object and pharmaceutical activity, it is more and more interested to researchers, and as the developing dominance structure molecule of new drug.But classical benzene
Benzofuran compound has the distinct disadvantage of poorly water-soluble, limits its application.It although can be by drawing on substrate parent
Enter water soluble group and improve water solubility, but compound activity reduction is often resulted in due to introducing extra functional group, increase in addition
Cost is added.Furopyridine class compound is the bioisostere of benzofuran class compound, but due to containing in structure
There is pyridine ring and there is preferable water solubility, and have lot of documents and report in relation to the medicinal of furopyridine class compound
Activity and value.It can be used to treat skin disease, be the nucleic acid reagent in biophysics field；With anticancer, anti-malignant cell proliferation,
The effect of antiviral, also acts as insecticide, prevents activity, the anti HIV-1 virus of cancerous tumor cell；It is often also used for treating more blood
Disease, hepatitis, promotes the diseases such as sleep, nervus retrogression at migraine.Important component in calcium blockers and phytoestrogen contains
Furopyridine class compound.
Furopyridine class compound is obtained or by the knot to furopyridine parent nucleus by artificial synthesized mode
Structure is modified and forms new furopyridine derivative, is the main side of current furopyridine class compound developmental research
To.Known synthetic method is confined to mostly using the pyridine of 2- halogen or 2- methoxy substitutions as raw material, is acted in metallic catalyst
Lower cyclization obtains furans simultaneously [2,3-b] pyridine compounds and their.But this method, due to the more difficult acquisition of raw material, products therefrom is limited,
It is not a kind of method of ideal synthesising target compound, thus does not apply widely yet.An only document report
Using pyridine nitric oxide as raw material, furans simultaneously [2,3-b] pyridine product, but this method is limited only to 3- is obtained with anhydride reaction
Synthesis of the position for furans simultaneously [2,3-b] pyridine of ester group.So universal synthesis method of exploitation azabenzofuran simple and effective
It is significant.
Invention content
The object of the present invention is to provide a kind of succinct synthetic methods of furopyridine class compound, and the present invention is with pyridine nitrogen
Oxide is substrate, and acetic anhydride is solvent, and potassium carbonate is alkali, and under 120~140 degree, reaction generates furans simultaneously [2,3-b] pyridine
Class compound.This method has easy to operate, and reaction selectivity is high, and substrate is easy to get, and applicability extensively waits remarkable advantages.It in addition, should
Class compound water soluble benzofuran compounds more corresponding than its significantly improve.
The purpose of the present invention is what is be achieved through the following technical solutions：
Simultaneously [2,3-b] pyridine compounds and their, general structure are as follows for a kind of furans：
Wherein, R is the hydrogen in the substitution of pyridine ring 4,5,6, halogen, nitro, aryl, carboxyl, trifluoromethyl, amide groups,
Ester group, alkyl or alkoxy.R1And R2For substituted hydrogen, aryl or alkyl；
Compound I is synthesized by the following way route and obtains：
Solvent used in the reaction is acetic anhydride.Alkali used is potassium carbonate, and reaction temperature is 120~140 degree, reacts duration
It is 6~14 hours.
The name of the furopyridine class compound synthesized and structure are as shown in table 1：
A kind of furopyridine class compound of table 1
The advantages and positive effects of the present invention：
1st, the present invention uses pyridine nitric oxide cheap and easy to get the reaction method invented is without metal catalytic for raw material
Agent has regioselectivity high, and substrate applicability is wide, and yield is high, environmentally protective to wait remarkable advantages.
2nd, key reaction of the invention is not required to anhydrous and oxygen-free operation, easy to operate, is suitble to large-scale production and exploitation.
3rd, the method for the present invention can obtain the furopyridine class compound of different location substitution, and suitable for all kinds of substitutions
Base.It can be promoted the use of with principle according to the invention, applicability is fine.
4th, furopyridine class compound according to the present invention is obtained than corresponding benzofuran class compound water soluble
It is obviously improved, but extra water soluble group is not introduced in precursor structure.
Description of the drawings
Fig. 1 is nucleus magnetic hydrogen spectrum figure of the compound 1 in deuterated chloroform；
Fig. 2 is nuclear-magnetism carbon spectrogram of the compound 1 in deuterated chloroform；
Fig. 3 is nucleus magnetic hydrogen spectrum figure of the compound 4 in deuterated chloroform；
Fig. 4 is nuclear-magnetism carbon spectrogram of the compound 4 in deuterated chloroform；
Fig. 5 is nucleus magnetic hydrogen spectrum figure of the compound 6 in deuterated chloroform；
Fig. 6 is nuclear-magnetism carbon spectrogram of the compound 6 in deuterated chloroform.
Specific embodiment
In order to understand the present invention, with reference to embodiment, the invention will be further described：Following embodiments are illustrative
, it is not limited, it is impossible to limit protection scope of the present invention with following embodiments.
A kind of furans simultaneously [2,3-b] pyridine compounds and their, it is characterised in that：General structure is as follows：
Wherein, R is the hydrogen in the substitution of pyridine ring 4,5,6, halogen, nitro, aryl, carboxyl, trifluoromethyl, amide groups,
Ester group, alkyl or alkoxy.R1And R2For substituted hydrogen, aryl or alkyl.
The present invention also provides a kind of furans simultaneously [2,3-b] pyridine compounds and their without metal catalytic synthetic method, step is such as
Under：
Compound II (1.0eq.) is sequentially added in round-bottomed flask, potassium carbonate (3.0eq.), water (7.0eq.) add in second
Acid anhydrides (concentration of substrate 0.2mol/L), is then heated to 120~140 degree of reactions, and TLC tracking reaction terminates (to need 6 until reaction
~14h).It is cooled to room temperature, adds in ethyl acetate and water, take upper organic phase.After being extracted twice to water phase, merge organic phase,
It is dry, crude product is obtained after concentration.Use petroleum ether：Ethyl acetate=30:1~20:1 is used as mobile phase, and column chromatography obtains I (1 institutes of table
Show each compound).
It is illustrated below by embodiment.
Embodiment 1
3- (2- oxopropyls)-pyridine nitric oxide (120mg), potassium carbonate (302mg), water are added in round-bottomed flask
(92 μ l) adds in acetic anhydride (3.6ml), is then heated to 120~140 degree of reactions, and TLC tracking reaction terminates (to need until reaction
Want 6~14h).It is cooled to room temperature, adds in ethyl acetate and water, take upper organic phase.After being extracted twice to water phase, merge organic
Phase, it is dry, crude product is obtained after concentration.Use petroleum ether：Ethyl acetate=30:1~20:1 is used as mobile phase, and column chromatography obtains 1
(60mg, 58%).Structural parameters:H NMR(400MHz,CDCl3) δ 8.18 (dd, J=4.8,1.6Hz, 1H), 7.68 (dd, J=
7.6,1.6Hz, 1H), 7.12 (dd, J=7.2,4.8Hz, 1H), 2.39 (s, 3H), 2.12 (s, 3H)；13C NMR(100MHz,
CDCl3)δ161.3,150.8,142.6,127.2,122.6,118.6,109.3,11.9,7.9.HRMS(+ESI-TOF)m/z:
[M+H]+calcd forC9H10NO 148.0757；found 148.0752.
Embodiment 2
The synthetic method of embodiment 2 leads to method with above-mentioned synthesis.
Ring closure reaction yield：47%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.19 (dd, J=4.8,0.8Hz,
1H), 7.75 (dd, J=7.6,1.2Hz, 1H), 7.13 (dd, J=7.6,4.2Hz, 1H), 2.61 (q, J=7.6Hz, 2H),
2.41 (s, 3H), 1.22 (t, J=7.6Hz, 3H)；13C NMR(100MHz,CDCl3)δ161.3,150.2,142.5,127.4,
121.6,118.4,115.5,16.9,14.3,11.9.HRMS(+ESI-TOF)m/z:[M+H]+calcd for C10H12NO
162.0913；found 162.0914.
Embodiment 3
The synthetic method of embodiment 3 leads to method with above-mentioned synthesis.
Ring closure reaction yield：49%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.15 (d, J=4.0Hz, 1H),
7.85 (d, J=7.2Hz, 1H), 7.10 (dd, J=7.2,4.8Hz, 1H), 3.07-3.00 (m, 1H), 2.40 (s, 3H), 1.34
(d, J=7.2Hz, 6H)；13C NMR(100MHz,CDCl3)δ161.3,149.2,142.4,128.5,120.6,119.6,
118.3,29.8,25.4,22.4,12.3.HRMS(+ESI-TOF)m/z:[M+H]+calcd forC11H14NO 176.1070；
found 176.1065.
Embodiment 4
The synthetic method of embodiment 4 leads to method with above-mentioned synthesis.
Ring closure reaction yield：55%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.18 (dd, J=4.8,1.6Hz,
1H), 7.50 (dd, J=7.6,1.6Hz, 1H), 7.30-7.27 (m, 2H), 7.22-7.19 (m, 3H), 7.05 (dd, J=7.6,
4.8Hz,1H),3.96(s,2H),2.48(s,3H)；13C NMR(100MHz,CDCl3)δ161.4,151.7,142.8,139.2,
128.7,128.4,128.0,126.5,121.7,118.7,112.8,29.8,12.2.HRMS(+ESI-TOF)m/z:[M+H]+
calcd for C15H14NO 224.1070；found 224.1069.
Embodiment 5
The synthetic method of embodiment 5 leads to method with above-mentioned synthesis.
Ring closure reaction yield：53%；Structural parameters:1H NMR(400MHz,CDCl3)δ8.21–8.20(m,1H),7.71
(dd, J=7.6,1.2Hz, 1H), 7.14 (dd, J=7.2,4.8Hz, 1H), 2.77 (q, J=7.6Hz, 2H), 2.15 (s, 3H),
1.31 (t, J=7.6Hz, 3H)；13C NMR(100MHz,CDCl3)δ161.3,155.6,142.6,127.3,122.6,118.5,
108.3,19.7,12.6,7.8.HRMS(+ESI-TOF)m/z:[M+H]+calcd forC10H12NO 162.0913,found
162.0915.
Embodiment 6
The synthetic method of embodiment 6 leads to method with above-mentioned synthesis.
Ring closure reaction yield：51%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.31 (dd, J=4.8,1.6Hz,
1H), 7.87-7.85 (m, 3H), 7.50 (t, J=7.6Hz, 2H), 7.39 (t, J=7.2Hz, 1H), 7.23 (dd, J=7.6,
4.8Hz,1H),2.49(s,3H)；13C NMR(100MHz,CDCl3)δ161.2,150.6,144.1,130.7,128.9,
128.6,128.2,127.1,123.5,119.0,110.5,9.7.HRMS(+ESI-TOF)m/z:[M+H]+calcd for
C14H12NO 210.0913；found 210.0911.
Embodiment 7
The synthetic method of embodiment 7 leads to method with above-mentioned synthesis.
Ring closure reaction yield：46%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.18 (dd, J=4.8,1.6Hz,
1H), 7.87 (dd, J=7.6,1.6Hz, 1H), 7.46 (d, J=7.2Hz, 2H), 7.28 (d, J=7.2Hz, 2H), 7.18 (t, J
=7.2Hz, 1H) 7.10 (dd, J=7.6,5.2Hz, 1H), 3.65 (d, J=10.8Hz, 1H), 3.28-3.17 (m, 1H),
2.74-2.62 (m, 1H), 1.41 (d, J=7.2Hz, 3H), 1.28 (d, J=7.2Hz, 3H), 0.92 (d, J=6.4Hz, 3H),
1.86 (d, J=6.4Hz, 3H)；13C NMR(100MHz,CDCl3)δ161.6,153.5,142.6,141.6,129.2,128.6,
128.5,126.7,120.23,120.18,118.4,52.0,31.8,25.6,22.7,22.5,21.9,21.6.HRMS(+ESI-
TOF)m/z:[M+H]+calcd for C20H24NO294.1852；found 294.1849.
Embodiment 8
The synthetic method of embodiment 8 leads to method with above-mentioned synthesis.
Ring closure reaction yield：59%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.29 (dd, J=4.8,1.2Hz,
1H), 8.03 (dd, J=7.6,1.2Hz, 1H), 7.73 (d, J=7.6Hz, 2H), 7.48 (t, J=7.2Hz, 2H), 7.39 (t, J
=7.6Hz, 1H), 7.18 (dd, J=7.6,4.8Hz, 1H), 3.48 (sep, J=6.8Hz, 1H), 1.46 (d, J=6.8Hz,
6H)；13C NMR(100MHz,CDCl3)δ161.5,149.6,143.7,130.6,130.1,128.8,128.7,128.1,
121.2,120.8,118.6,25.7,22.5.HRMS(+ESI-TOF)m/z:[M+H]+calcd for C16H16NO
238.1226；found 238.1219.
Embodiment 9
The synthetic method of embodiment 9 leads to method with above-mentioned synthesis.
Ring closure reaction yield：50%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.14 (dd, J=2.8,1.6Hz,
1H), 7.81-7.79 (m, 2H), 7.58 (dd, J=8.0,2.8Hz, 1H), 7.52-7.48 (m, 2H), 7.44-7.40 (m, 1H),
2.91 (q, J=7.6Hz, 2H), 1.37 (t, J=7.2Hz, 3H)；13C NMR(100MHz,CDCl3)δ158.5,157.4,
156.1,152.6,131.8 (d, J=30.0Hz), 130.3,129.0 (d, J=21.0Hz), 127.3,123.2 (d, J=
7.0Hz), 117.2 (d, J=4.0Hz), 114.6 (d, J=22.0Hz), 17.8,14.1.HRMS (+ESI-TOF) m/z:[M+H
]+calcd for C15H13NOF 242.0976,found 242.0970.
Embodiment 10
The synthetic method of embodiment 10 leads to method with above-mentioned synthesis.
Ring closure reaction yield：61%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.12 (s, 1H), 7.81 (d, J=
7.6Hz, 2H), 7.69 (s, 1H), 7.48 (t, J=7.6Hz, 2H), 7.39 (t, J=7.2Hz, 1H), 2.92 (q, J=7.6Hz,
2H), 2.45 (s, 3H), 1.37 (t, J=7.6Hz, 3H)；13C NMR(100MHz,CDCl3)δ160.0,150.3,144.5,
130.8,128.9,128.64,128.60,128.2,127.2,122.2,116.7,18.6,17.8,14.3.HRMS(+ESI-
TOF)m/z:[M+H]+calcd for C16H16NO 238.1226,found 238.1221.
Embodiment 11
The synthetic method of embodiment 11 leads to method with above-mentioned synthesis.
Ring closure reaction yield：62%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.52 (d, J=2.0Hz, 1H),
8.00 (d, J=2.0Hz, 1H), 7.88 (d, J=7.6Hz, 2H), 7.65-7.64 (m, 2H), 7.53-7.48 (m, 4H), 7.43-
7.39(m,2H),2.52(s,3H)；13C NMR(100MHz,CDCl3)δ160.7,151.4,143.1,138.7,133.1,
130.6,129.1,128.9,128.7,127.7,127.6,127.1,126.7,123.5,110.7,9.7.HRMS(+ESI-
TOF)m/z:[M+H]+calcd for C20H16NO 286.1226；found286.1224.
Embodiment 12
The synthetic method of embodiment 12 leads to method with above-mentioned synthesis.
Ring closure reaction yield：76%；Structural parameters:1H NMR(400MHz,CDCl3) δ 8.35 (dd, J=4.8,1.2Hz,
1H), 7.83 (dd, J=7.6,1.2Hz, 1H), 7.73-7.70 (m, 2H), 7.49-7.42 (m, 5H), 7.32 (dd, J=6.4,
3.6Hz, 3H), 7.23 (dd, J=8.0,5.2Hz, 1H)；13C NMR(100MHz,CDCl3)δ161.2,150.3,144.5,
132.1,129.9,129.7,129.3,129.1,129.0,128.6,128.2,127.5,122.7,119.6,116.6.HRMS
(+ESI-TOF)m/z:[M+H]+calcd for C19H14NO 272.1070；found 272.1065.
Embodiment 13
The synthetic method of embodiment 13 leads to method with above-mentioned synthesis.
Ring closure reaction yield：46%；Structural parameters:1H NMR(400MHz,CDCl3) δ 7.77 (d, J=8.0Hz, 1H),
7.68-7.66(m,2H),7.49–7.44(m,5H),7.34–7.33(m,3H),7.26(s,1H)；13C NMR(100MHz,
CDCl3)δ159.9,150.8,146.0,131.6,131.0,129.6,129.40,129.37,128.8,128.4,127.3,
121.4,120.0,116.5.HRMS(+ESI-TOF)m/z:[M+H]+calcd forC19H13ClNO 306.0680；found
306.0677.
In order to study application of the furopyridine compound in terms of water solubility is improved, we have chosen the portion of above-mentioned synthesis
Point furopyridine and corresponding benzofuran calculate its lipid LogP, as a result as shown in table 2 below.
2 furopyridine of table and the water-soluble of benzofuran class compound are compared
Table 2 the result shows that, the lipid LogP of furopyridine compound is smaller than corresponding benzofuran about
0.6 unit, therefore the water solubility of furopyridine class compound is significantly improved than corresponding benzofuran class compound.
Claims (6)
1. a kind of furans simultaneously [2,3-b] pyridine compounds and their, it is characterised in that：General structure is as follows：
Wherein, R is the hydrogen in the substitution of pyridine ring 4,5,6, halogen, nitro, aryl, carboxyl, trifluoromethyl, amide groups, ester group,
Alkyl or alkoxy.R1And R2For substituted hydrogen, aryl or alkyl.
2. furans according to claim 1 simultaneously [2,3-b] pyridine compounds and their, it is characterised in that：The furans simultaneously [2,3-
B] pyridine compounds and their structure it is as follows：
3. a kind of furans simultaneously [2,3-b] pyridine compounds and their without metal catalytic synthetic method, it is characterised in that：Its synthetic route
It is as follows：I.e. using pyridine nitric oxide II as raw material, acetic anhydride is solvent, and potassium carbonate is alkali, and under heating condition, such is obtained by the reaction
Compound；
4. furans according to claim 3 simultaneously [2,3-b] pyridine compounds and their without metal catalytic synthetic method, feature
It is：The solvent is acetic anhydride.
5. furans according to claim 3 simultaneously [2,3-b] pyridine compounds and their without metal catalytic synthetic method, feature
It is：Reaction temperature is 120~140 degree, a length of 6~14 hours during reaction.
6. simultaneously [2,3-b] pyridine compounds and their is water-soluble in raising benzofuran compounds for furans according to claim 1
Application in terms of property.
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