CN108129480A - A kind of preparation method of the indolizine of methylene containing heteroaromatic derivative - Google Patents
A kind of preparation method of the indolizine of methylene containing heteroaromatic derivative Download PDFInfo
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- CN108129480A CN108129480A CN201810197377.9A CN201810197377A CN108129480A CN 108129480 A CN108129480 A CN 108129480A CN 201810197377 A CN201810197377 A CN 201810197377A CN 108129480 A CN108129480 A CN 108129480A
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- indolizine
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a kind of preparation method of the indolizine of methylene containing heteroaromatic derivative, including：（1）Weigh raw material in molar ratio, 1 part of 52 phenyl indolizine of methyl, 1 part of miscellaneous aldehyde of virtue, the 1.3 parts of Chinese this esters, 47 94 parts of toluene, 0.05 0.1 parts of p-methyl benzenesulfonic acids；（2）5 methyl, 2 phenyl indolizine, the miscellaneous aldehyde of virtue and Han Si esters are dissolved in toluene successively, add catalyst p-methyl benzenesulfonic acid, 60 DEG C of stirrings 12~for 24 hours；（3）It will（2）Obtained solution is cooled to room temperature, and decompression is spin-dried for solvent；（4）It will（3）Obtained solid phase obtains heteroaromatic methylene indolizine derivative through column chromatography for separation.Raw material needed for the present invention is easy to get and economy, eliminates the need for noble metal and makees catalyst, further reduced synthesis cost, eliminates possible heavy metal pollution.The present invention is three component one-pot synthesis, and step is simple, easily operated, high income.
Description
Technical field
The invention belongs to organic drug synthesis technical field, the method for specifically a kind of synthesis pyrazines derivatives.
Background technology
In organic compound into in pharmaceutical synthesis, pyrazine and its derivative are the important source materials of synthesizing activity natural products,
With the important biology and pharmacological activity such as antibacterial, anti-hypertension, antitumor and anti-arrhythmia, therefore widely weighed
Depending on.However, how cost-effectively to synthesize pyrazine and its derivative is synthesis hot spot.At present, to the system of pyrazine and its derivative
Preparation Method has very much, and main method is that new group is introduced in the 3- positions of indolizine, such as：（1）Org. Lett.,6(7), 1159- 1162,2004
For another example：（2）Org. Biomol. Chem., 13, 10986–10994,2015
Also such as：（3）Org. Biomol. Chem., 10, 7108–7119, 2012
For another example（4）Org. Lett.,13(6), 1342- 1345,2011
Above-mentioned several synthetic methods can obtain indolizine derivative in the new substituent group of 3- introducings of indolizine.But there are two altogether
Property the defects of, first, regioselectivity is poor, second is that expensive metallic catalyst causes synthesis cost to remain high.Chinese patent
201180042948.8 the indolizine derivative preparation method of some 3- oxo, step are disclosed in（1）By compoundWith compoundIt is condensed, but is not disclosed the reaction condition and yield of the condensation；（2）
Carry out macromolecule alkali for hydrolysis；（3）Carry out esterification；（4）It is reacted again with N- bromosuccinimide；（5）Undergo triphosgene
Effect, obtain corresponding isocyanates, then carry out amine condensation, obtain corresponding urea；（6）Urea in alkaline medium to obtaining
Carry out cyclization；（7）Finally in the presence of palladium catalyst, ligand and alkali, with phenyl boronic acid derivative or heteroaryl-boronic acids
Su Chuji coupling reactions occur for derivative or phenylboric acid ester derivant or heteroaryl-boronic acids ester derivant, obtain corresponding indolizine
Derivative.The technical solution is the problem is that yield is relatively low, cumbersome complexity, and synthesis cost is high, it is impossible to meet scale
Production requirement.
It would therefore be highly desirable to research and develop, a kind of raw material is easy to get, yield is high, heteroaromatic methylene indolizine derivative synthesis side at low cost
Method.
Invention content
In view of the problems of the existing technology, the present invention provides a kind of indolizine derivative of methylene containing heteroaromatic and its synthesis
Method.
The present invention reaction mechanism be：
According to above-mentioned reaction mechanism, the present invention adopts the following technical scheme that：
A kind of indolizine derivative of methylene containing heteroaromatic, structural formula are：
Wherein R1For H, CH3；R2For heterocycles such as pyridyl group, furyl, thienyl, pyrrole radicals, indyl, quinolyls.
The preparation method of the indolizine derivative of methylene containing heteroaromatic of the present invention, includes the following steps：
（1）Weigh raw material in molar ratio, 1 part of 5- methyl -2- phenyl indolizine, 1 part of miscellaneous aldehyde of virtue, the 1.3 parts of Chinese this esters, 47-94 parts of first
Benzene, 0.05-0.1 parts of p-methyl benzenesulfonic acids；
（2）5- methyl -2- phenyl indolizine, the miscellaneous aldehyde of virtue and Han Si esters are dissolved in toluene successively, add catalyst to methylbenzene
Sulfonic acid, 60 DEG C of stirrings 12~for 24 hours；
（3）It will（2）Obtained solution is cooled to room temperature, and decompression is spin-dried for solvent；
（4）It will（3）Obtained solid phase obtains heteroaromatic methylene indolizine derivative through column chromatography for separation.
The structural formula of the indolizine raw material is：。
The miscellaneous aldehyde of virtue includes pyridine carboxaldehyde, thiophenecarboxaldehyde, furtural, pyrrole aldehyde, the indoles of different substitution positions
Formaldehyde, quinoline aldehyde, structural formula are：。
The structural formula of described this ester of the Chinese is：。
The raw material or reagent that the present invention uses are commercially available.
Compared with prior art, the advantage of the invention is that：（1）Raw material is easy to get and economy；Synthesis side of the invention is required
It is all that market is easy to purchase that raw material, which includes indolizine derivative, the miscellaneous aldehyde of virtue, the Chinese this ester, p-methyl benzenesulfonic acid and toluene, above-mentioned raw materials,
Chemicals, and compared with the raw material needed for the prior art, raw material economics, material benefit, initial estimate, present invention synthesis heteroaromatic is sub-
The cost of methyl indolizine derivative only has the 50% of the prior art.（2）It eliminates the need for noble metal and makees catalyst, on the one hand further
Synthesis cost is reduced, on the other hand without possible heavy metal pollution, belongs to environmentally friendly synthetic method.（3）Operation letter
Single, the present invention is three component one-pot synthesis, and step is simple, easily operated, and the requirement to operating personnel is relatively low, easy to spread to answer
With.（4）High income, it is demonstrated experimentally that the yield of synthetic method of the present invention is more than 90%.
Description of the drawings
Fig. 1 is 5- methyl 2- phenyl -3-（Pyridine -3- methylene）The nuclear magnetic resonance spectroscopy of indolizine.
Fig. 2 is 5- methyl 2- phenyl -3-（Pyridine -3- methylene）The carbon-13 nmr spectra of indolizine.
Fig. 3 is 5- methyl 2- phenyl -3-（Pyridine -4- methylene）The nuclear magnetic resonance spectroscopy of indolizine.
Fig. 4 is 5- methyl 2- phenyl -3-（Pyridine -4- methylene）The carbon-13 nmr spectra of indolizine.
Fig. 5 is 5- methyl 2- phenyl -3-（Pyridine -2- methylene）The nuclear magnetic resonance spectroscopy of indolizine.
Fig. 6 is 5- methyl 2- phenyl -3-（Pyridine -2- methylene）The carbon-13 nmr spectra of indolizine.
Fig. 7 is 5- methyl 2- phenyl -3-（Thiophene -3- methylene）The nuclear magnetic resonance spectroscopy of indolizine.
Fig. 8 is 5- methyl 2- phenyl -3-（Thiophene -3- methylene）The carbon-13 nmr spectra of indolizine.
Fig. 9 is 5- methyl 2- phenyl -3-（Furans -2- methylene）The nuclear magnetic resonance spectroscopy of indolizine.
Figure 10 is 5- methyl 2- phenyl -3-（Furans -2- methylene）The carbon-13 nmr spectra of indolizine.
Embodiment 1
1 mmol 5- methyl -2- phenyl indolizines are added in 50 mL round-bottomed flasks（207 mg）, 1 mmol β-pyridine carboxaldehyde
（107 mg）, the 1.3 mmol Chinese this ester（330 mg）, 94mmol toluene（10 mL）, 0.1 mmol pairs is added after stirring and dissolving
Toluenesulfonic acid（17 mg）, 60 DEG C are stirred to react for 24 hours, are cooled to room temperature, and decompression is spin-dried for solvent, and column chromatography for separation obtains brown production
277 mg of object, yield 93%.Structural formula：
Chinese：5- methyl 2- phenyl -3-（Pyridine -3- methylene）Indolizine
Appearance：Brown solid
Fusing point：159-162 ℃
Nuclear magnetic resonance spectroscopy (400MHz, CDCl3, internal standard: TMS)； δ： 8.51 – 8.36 (m, 2H), 7.45
(dt, J = 15.8, 7.8 Hz, 4H), 7.39 – 7.33 (m, 3H), 7.25 (d, J = 7.8 Hz, 1H),
7.17 (dd, J = 7.7, 4.7 Hz, 1H), 6.66 (dd, J = 8.9, 6.6 Hz, 1H), 6.42 (t, J =
6.7 Hz, 1H), 4.30 (s, 2H), 2.38 (s, 3H)；The result is shown in Figure 1.
Carbon-13 nmr spectra (400MHz, CDCl3, internal standard: TMS)； δ：149.49, 147.82, 135.52,
135.27, 134.08, 130.18, 129.98, 129.28, 128.38, 126.69, 123.66, 121.62,
117.60, 116.42, 115.26, 110.35, 106.20, 27.78, 9.31；As a result see Fig. 2.
Embodiment 2
1 mmol 5- methyl -2- phenyl indolizines are added in 50 mL round-bottomed flasks（207 mg）, 1 mmol γ-pyridine formaldehyde
（107 mg）, the 1.3 mmol Chinese this ester（330 mg）, 47mmol toluene（5 mL）, 0.1mmol is added to first after stirring and dissolving
Base benzene sulfonic acid（17 mg）, 60 DEG C are stirred to react 18h, are cooled to room temperature, and are spin-dried for solvent, and column chromatography for separation obtains brown solid
283 mg, yield 95%.Structural formula：
Chinese：5- methyl 2- phenyl -3-（Pyridine -4- methylene）Indolizine
Appearance：Brown solid
Fusing point： 168-171 ℃
Nuclear magnetic resonance spectroscopy (400MHz, CDCl3, internal standard: TMS)；δ：8.50 (d,J = 5.9 Hz, 2H), 7.51
– 7.34 (m, 7H), 6.99 (d, J = 5.5 Hz, 2H), 6.68 (dd, J = 8.8, 6.5 Hz, 1H),
6.43 (t, J= 6.8 Hz, 1H), 4.28 (s, 2H), 2.39 (s, 3H)；As a result see Fig. 3.
Carbon-13 nmr spectra (400MHz, CDCl3, internal standard: TMS)；δ：150.06, 147.89, 135.43,
130.12, 129.47, 128.40, 126.73, 123.19, 121.65, 117.63, 115.83, 115.38,
110.39, 106.22, 29.94, 9.34；As a result see Fig. 4.
Embodiment 3
1 mmol 5- methyl -2- phenyl indolizines are added in 50 mL round-bottomed flasks（207 mg）, 1 mmol α-pyridine carboxaldehyde
（107 mg）, the 1.3 mmol Chinese this ester（330 mg,）, 65.8mmol toluene（7 mL）, 0.05 is added after stirring and dissolving
Mmol p-methyl benzenesulfonic acids（8.5mg）, 60 DEG C are stirred to react 12h, are cooled to room temperature, and are spin-dried for solvent, and column chromatography for separation obtains brown
269 mg of solid product, yield 90%.Structural formula
Chinese：5- methyl 2- phenyl -3-（Pyridine -2- methylene）Indolizine
Appearance：Brown solid
Fusing point：164-166 ℃
Nuclear magnetic resonance spectroscopy (400MHz, CDCl3, internal standard: TMS)； δ：8.59 (d,J = 4.2 Hz, 1H), 7.71
(d, J = 7.0 Hz, 1H), 7.60 – 7.35 (m, 7H), 7.19 – 7.02 (m, 1H), 6.82 (d, J =
7.8 Hz, 1H), 6.69 – 6.61 (m, 1H), 6.42 (t, J = 6.7 Hz, 1H), 4.49 (s, 2H),
2.40 (s, 3H)；As a result see Fig. 5.
Carbon-13 nmr spectra (400MHz, CDCl3, internal standard: TMS)；δ：158.94, 149.38, 136.80,
135.73, 130.30, 129.87, 128.91, 128.33, 126.57, 122.31, 122.02, 121.47,
117.38, 117.12, 115.21, 110.04, 106.06, 33.68, 9.39; HRMS (ESI): calcd. For
C24H24NO2(M+H): 358.1807; found: 358.1800；As a result see Fig. 6.
Embodiment 4
1 mmol 5- methyl -2- phenyl indolizines are added in 50 mL round-bottomed flasks（207 mg）, 1 mmol β-thiophenecarboxaldehyde
（112 mg）, the 1.3 mmol Chinese this ester（330 mg）, 56.4mmol toluene（6 mL）, 0.08 mmol is added after stirring and dissolving
P-methyl benzenesulfonic acid（13.6 mg,）, 60 DEG C are stirred to react 16h, are cooled to room temperature, and are spin-dried for solvent, and column chromatography for separation obtains brown and consolidates
270 mg of body product, yield 91%.Structural formula：
Chinese：5- methyl 2- phenyl -3-（Thiophene -3- methylene）Indolizine
Appearance：Brown solid
Fusing point：149-151 ℃
Nuclear magnetic resonance spectroscopy (400MHz, CDCl3, internal standard: TMS)；δ：7.59 (d,J = 7.1 Hz, 1H), 7.50
– 7.41 (m, 5H), 7.37 (t, J = 7.0 Hz, 1H), 7.29 (t, J = 3.9 Hz, 1H), 6.88 (d,J = 4.9 Hz, 1H), 6.81 (d, J = 1.6 Hz, 1H), 6.67 (dd, J = 8.9, 6.5 Hz, 1H),
6.44 (t, J= 6.7 Hz, 1H), 4.27 (s, 2H), 2.41 (s, 3H)；As a result see Fig. 7.
Carbon-13 nmr spectra (400MHz, CDCl3, internal standard: TMS)；δ：139.06, 135.78, 130.24,
129.71, 128.27, 127.71, 126.47, 126.00, 122.06, 120.83, 118.16, 117.44,
114.95, 109.98, 105.83, 25.80, 9.41; HRMS (ESI): calcd. For C20H18NS (M+H):
304.1162; found: 304.1169；As a result see Fig. 8.
Embodiment 5
1 mmol 5- methyl -2- phenyl indolizines are added in 50 mL round-bottomed flasks（207 mg）, 1 mmol furaldehydes
（96 mg）, the 1.3 mmol Chinese this ester（330 mg）, 84.6mmol dry toluenes（9 mL）, 0.1 is added after stirring and dissolving
Mmol p-methyl benzenesulfonic acids（17 mg）, 60 DEG C are stirred to react 22h, are cooled to room temperature, and are spin-dried for solvent, and column chromatography for separation obtains brown
261 mg of solid product, yield 91%.Structural formula
Chinese：5- methyl 2- phenyl -3-（Furans -2- methylene）Indolizine
Appearance：Brown solid
Fusing point：178-180℃;
Nuclear magnetic resonance spectroscopy (400MHz, CDCl3, internal standard: TMS)；δ：7.77 (d,J = 7.1 Hz, 1H), 7.55
– 7.47 (m, 4H), 7.46 – 7.39 (m, 3H), 6.71 (dd, J = 8.7, 6.7 Hz, 1H), 6.52 (t,J = 6.3 Hz, 1H), 6.41 – 6.27 (m, 1H), 5.98 (d, J = 2.4 Hz, 1H), 4.27 (s, 2H),
2.42 (s, 3H)；As a result see Fig. 9.
Carbon-13 nmr spectra (400MHz, CDCl3, internal standard: TMS)；δ：152.25, 141.55, 135.58,
130.38, 129.91, 128.59, 128.27, 126.56, 122.12, 117.45, 115.59, 115.15,
110.42, 110.06, 106.19, 105.94, 24.26, 9.39; HRMS (ESI): calcd. For C20H18NO
(M+H): 288.1383; found: 238.1389；The result is shown in Figure 10.
Claims (4)
1. a kind of preparation method of the indolizine of methylene containing heteroaromatic derivative, includes the following steps：
（1）Weigh raw material in molar ratio, 1 part of 5- methyl -2- phenyl indolizine, 1 part of miscellaneous aldehyde of virtue, the 1.3 parts of Chinese this esters, 47-94 parts of first
Benzene, 0.05-0.1 parts of p-methyl benzenesulfonic acids；
（2）5- methyl -2- phenyl indolizine, the miscellaneous aldehyde of virtue and Han Si esters are dissolved in toluene successively, add catalyst to methylbenzene
Sulfonic acid, 60 DEG C of stirrings 12~for 24 hours；
（3）It will（2）Obtained solution is cooled to room temperature, and decompression is spin-dried for solvent；
（4）It will（3）Obtained solid phase obtains heteroaromatic methylene indolizine derivative through column chromatography for separation.
A kind of 2. preparation method of the indolizine of methylene containing heteroaromatic derivative according to claim 1, which is characterized in that institute
The structural formula of indolizine raw material stated is：。
A kind of 3. preparation method of the indolizine of methylene containing heteroaromatic derivative according to claim 1, which is characterized in that institute
The miscellaneous aldehyde of virtue stated includes the different pyridine carboxaldehydes for replacing positions, thiophenecarboxaldehyde, furtural, pyrrole aldehyde, indolecarboxaldehyde, quinoline first
Aldehyde, structural formula are：。
A kind of 4. preparation method of the indolizine of methylene containing heteroaromatic derivative according to claim 1, which is characterized in that institute
The structural formula for the Chinese this ester stated is：。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175021A (en) * | 2019-07-02 | 2021-01-05 | 成都先导药物开发股份有限公司 | Method for synthesizing On-DNA aryl benzyl substituted compound |
Citations (2)
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|---|---|---|---|---|
| JP2000311787A (en) * | 1999-02-22 | 2000-11-07 | Mitsui Chemicals Inc | Organic electroluminescent element |
| CN106661019A (en) * | 2014-06-17 | 2017-05-10 | 奇斯药制品公司 | Indolizine derivatives as phoshoinositide 3-kinases inhibitors |
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2018
- 2018-03-11 CN CN201810197377.9A patent/CN108129480A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000311787A (en) * | 1999-02-22 | 2000-11-07 | Mitsui Chemicals Inc | Organic electroluminescent element |
| CN106661019A (en) * | 2014-06-17 | 2017-05-10 | 奇斯药制品公司 | Indolizine derivatives as phoshoinositide 3-kinases inhibitors |
Non-Patent Citations (2)
| Title |
|---|
| FU-MIN CHEN: "Direct C–H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions", 《ORGANIC CHEMISTRY FRONTIERS》 * |
| MAMEDOV, VA ETAL: "An efficient one-step method for the synthesis of 2-(indolizin-2-yl)benzimidazoles from quinoxalinones and alpha-picoline via a novel rearrangement", 《TETRAHEDRON LETTERS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175021A (en) * | 2019-07-02 | 2021-01-05 | 成都先导药物开发股份有限公司 | Method for synthesizing On-DNA aryl benzyl substituted compound |
| CN112175021B (en) * | 2019-07-02 | 2022-08-16 | 成都先导药物开发股份有限公司 | Method for synthesizing On-DNA aryl benzyl substituted compound |
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Application publication date: 20180608 |