CN104496875A - Synthesis method of 2-allyl-2-formaldehyde-N-phenyl pyrroline - Google Patents
Synthesis method of 2-allyl-2-formaldehyde-N-phenyl pyrroline Download PDFInfo
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- ILDVYFKROJGRCU-UHFFFAOYSA-N CC(C(CCC1)(C=O)N1c(cc1)ccc1OC)C=C Chemical compound CC(C(CCC1)(C=O)N1c(cc1)ccc1OC)C=C ILDVYFKROJGRCU-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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Abstract
The invention discloses a synthesis method of 2-allyl-2-formaldehyde-N-phenyl pyrroline and belongs to the technical field of chemical pharmacy and fine chemical preparation. One-pot synthesis of polysubstituted and polyfunctionalized 2-allyl-2-formaldehyde-N-phenyl pyrroline is realized, metal-catalyzed sulfonyl triazole is decomposed into metal carbine, then metal carbene cyclization is carried out, and high-added-value 2-allyl-2-formaldehyde-N-phenyl pyrroline is efficiently obtained. The synthesis method of 2-allyl-2-formaldehyde-N-phenyl pyrroline has the advantages that a first technical route is provided for efficiently preparing a functionalized 2-allyl-2-formaldehyde-N-phenyl pyrroline derivative and the synthesis method of the 2-allyl-2-formaldehyde-N-phenyl pyrroline derivative can be widely applied in the field of chemical pharmacy and fine chemical engineering.
Description
Technical field
The invention belongs to chemical pharmacy and fine chemistry industry preparing technical field, namely one kettle way is prepared 2-allyl group pyrrole and is coughed up Lin 2-formaldehyde, especially relates to the Cabbeen cyclisation rearrangement reaction of metal catalytic, and the pyrrole containing quaternary carbon generating a kind of multifunctional dough efficiently coughs up Lin structure.The present invention is that the functionalized Bi Ka Lin derivative of efficient preparation provides a technical strategies and layout strategy, has wide application at chemical pharmacy and field of fine chemical.
Background technology
It is the important organic compound of a large class that pyrrole coughs up Lin, and a lot of compound containing this class formation has special chemistry and biological activity, is also present in many natural products and drug molecule.And the organic molecule of Bi Ka Lin compounds high added value especially containing aldehyde radical and alkene phenyl because aldehyde radical and alkene phenyl can very easily further derivatize obtain the nitrogen heterocyclic of other structure a lot.2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin is because containing multiple functional group in its structure, and should be the very valuable nitrogen heterocyclic of a class, the preparation method of this compounds also have no report at present.
Summary of the invention
The object of the invention is to set forth a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin preparation method, is exactly invented a kind of efficient one kettle way to prepare 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin specifically.
For realizing above-mentioned synthesis object, the present invention adopts following technical scheme, is summarised as shown reaction equation: (formula 1).In appropriate solvent, the cyclisation under suitable metal catalyst catalysis of various 1-alkylsulfonyl triazole 1 is reset, and obtains 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin 2 after suitable hydrolysis treatment.
R in general formula of molecular structure 1,2
1for various substituting group (be specially neighbour, to methoxyl group, alkyl, halogen etc.); R
2for the alkyl (being specially methyl, ethyl, benzyl etc.), various fat base (being specially methyl esters, ethyl ester etc.), various halogen (being specially chlorine, bromine, fluorine) etc. of the aryl (being specially phenyl, p-methylphenyl etc.) of various replacement, various replacement; R3 is the aryl etc. of various alkyl, various replacement.
A synthetic method for 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin, carry out according to following step:
1-alkylsulfonyl triazole 1, metal catalyst are blended in a kind of organic solvent and stir by a certain percentage, and according to substrate and specificity of reagent, temperature controls between certain temperature; after certain hour, stopped reaction, adds proper amount of methanol; salt of wormwood and a small amount of water, stirring is spent the night.With organic solvent ethyl acetate or dichloromethane extraction three times, with saturated common salt washing after organic phase merges, then use anhydrous sodium sulfate drying, remove solvent under reduced pressure, residue with Ethyl acetate and sherwood oil are eluent, silica gel column chromatogram separating purification, obtain corresponding nitrogen heterocyclic aldehyde 2.Or remove organic solvent under reduced pressure after having reacted, the direct silica gel chromatographic column of residue is separated.
The structural formula of wherein said 1-alkylsulfonyl triazole 1 is
wherein R
1for various substituting group (be specially neighbour, to methoxyl group, alkyl, halogen etc.); R
2for the alkyl (being specially methyl, ethyl, benzyl etc.), various fat base (being specially methyl esters, ethyl ester etc.), various halogen (being specially chlorine, bromine, fluorine) etc. of the aryl (being specially phenyl, p-methylphenyl etc.) of various replacement, various replacement; R
3for various alkyl, the aryl etc. of various replacement.
Wherein said solvent is the non-polar solvents such as tetrahydrofuran (THF), toluene, methylene dichloride, trichloromethane, 1,2-methylene dichloride.
Wherein said 1-alkylsulfonyl triazole 1, catalyst molar ratio are between 1.0:0.005 to 1.0:0.05.
Wherein said catalyzer is rhodium compound and the trifluoromethanesulfonic acids such as rhodium acetate, rhodium caprylate, m-phthalic acid rhodium, the silver salt such as copper compound and silver trifluoromethanesulfonate such as trifluoracetic acid copper.
Wherein said temperature of reaction is between 50-120 degree.
The wherein said reaction times is between 10 minutes to 5 hours.
Advantage of the present invention
1, this operation is easy, only needs one pot reaction just can prepare two kinds of nitrogen heterocyclics efficiently.
2, the product structure of this reaction is novel, goes out outside the method for this patent report, temporarily without other preparation method.
3, the product of this reaction is the compound of high added value.
Embodiment
Below by example, the present invention is described further:
Following non-limiting example 1-3# or comparative example 1-2# is used for explaining and the present invention is described; instead of limit the invention; in the protection domain of spirit of the present invention and claim, any amendment make the present invention and change, all belong to protection scope of the present invention.
Raw material used in the present invention, reagent and catalyzer are by reference to pertinent literature preparation, and solvent is through purifying and refine.
Embodiment 1
2 mmole 1-are blended in 10 milliliters of toluene are stirred toluene sulfo group triazole 1k, 0.01 mmole rhodium acetate, and temperature controls 120 degree, after 2 hours, stops heating, adds 2 ml methanol, 5 mmole salt of wormwood and a water, stirring at room temperature 12 hours.With organic solvent extraction into ethyl acetate three times, with saturated common salt washing after organic phase merges, then use anhydrous sodium sulfate drying, remove solvent under reduced pressure, residue with Ethyl acetate and sherwood oil are eluent, silica gel column chromatogram separating purification, obtain corresponding nitrogen heterocyclic aldehyde 2a (see table 1).Or remove organic solvent under reduced pressure after having reacted, the direct silica gel chromatographic column of residue is separated.
Embodiment 2
2 mmole 1-are blended in 10 milliliters of ethylene dichloride are stirred toluene sulfo group triazole 1g, 0.1 mmole rhodium acetate, and temperature controls 50 degree, after 5 hours, stops heating, adds 2 ml methanol, 5 mmole salt of wormwood and a water, stirring at room temperature 8 hours.With organic solvent extraction into ethyl acetate three times, with saturated common salt washing after organic phase merges, then use anhydrous sodium sulfate drying, remove solvent under reduced pressure, residue with Ethyl acetate and sherwood oil are eluent, silica gel column chromatogram separating purification, obtain corresponding nitrogen heterocyclic aldehyde 2g (see table 1).Or remove organic solvent under reduced pressure after having reacted, the direct silica gel chromatographic column of residue is separated.
Embodiment 3
2 mmole 1-are blended in 10 milliliters of toluene are stirred toluene sulfo group triazole 1i, 0.04 mmole rhodium acetate, and temperature controls 120 degree, after 10 minutes, stops heating, adds 2 ml methanol, 5 mmole salt of wormwood and a water, stirring at room temperature 12 hours.With organic solvent extraction into ethyl acetate three times, with saturated common salt washing after organic phase merges, then use anhydrous sodium sulfate drying, remove solvent under reduced pressure, residue with Ethyl acetate and sherwood oil are eluent, silica gel column chromatogram separating purification, obtain corresponding nitrogen heterocyclic aldehyde 2i (see table 1).Or remove organic solvent under reduced pressure after having reacted, the direct silica gel chromatographic column of residue is separated.
2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin prepared by table 1.
2a: yellow oil, 66%;
1h NMR (400MHz, CDCl
3) δ 9.59 (s, 1H), 6.81 (d, J=8.9Hz, 2H), 6.69 (m, 2H), 5.67-5.56 (m, 1H), 5.06 (brs, 1H), 5.03 (brs, 1H), 3.75 (s, 3H), 3.60-3.46 (m, 2H), 2.87 (dd, J=14.4,6.2Hz, 1H), 2.59 (dd, J=14.3,8.4Hz, 1H), 2.19-2.00 (m, 4H); 13C NMR (100MHz, CDCl
3) δ 204.1,133.3,118.8,114.9,114.4,71.9,55.8,50.9,35.1,33.9,23.5; HRMS (ESI) m/z theoretical value for C
15h
19nO
2na
+[M+Na]
+268.1308, measured value 268.1302.
2b: yellow oil, 64%;
1h NMR (300MHz, CDCl
3) δ 9.59 (s, 1H), 7.24-7.15 (m, 2H), 6.73 (t, J=7.3Hz, 1H), 6.60 (d, J=8.0Hz, 2H), 5.74-5.56 (m, 1H), 5.10-5.04 (m, 1H), 5.02 (m, 1H), 3.64-3.43 (m, 2H), 2.93 (dd, J=14.5,6.3Hz, 1H), 2.63 (dd, J=14.5,8.5Hz, 1H), 2.18-1.96 (m, 4H);
13c NMR (75MHz, CDCl3) δ 204.2,145.5,133.2,129.4,118.9,117.2,112.8,71.9,50.5,35.1,34.1,23.4; HRMS (ESI) m/z theoretical value for C
14h
18nO
+[M+H]
+216.1383, measured value 216.1375.
2c: yellow oil, 65%;
1h NMR (400MHz, CDCl
3) δ 9.60 (s, 1H), 7.02 (d, J=8.3Hz, 2H), 6.54 (d, J=8.4Hz, 2H), 5.66 (ddd, J=16.7,8.5,6.5Hz, 1H), 5.08 (d, J=6.9Hz, 1H), 5.04 (brs, 1H), 3.58-3.47 (m, 2H), 2.91 (dd, J=14.4,6.2Hz, 1H), 2.62 (dd, J=14.4,8.5Hz, 1H), 2.26 (s, 3H), 2.15-1.99 (m, 4H);
13c NMR (100MHz, CDCl
3) δ 204.3,143.3,133.4,129.9,126.4,118.7,112.9,71.8,50.5,35.1,34.3,23.4,20.3; HRMS (ESI) m/z theoretical value for C
15h
20nO
+[M+H]
+230.1539, measured value 230.1531.
2d: yellow oil, 68%;
1h NMR (400MHz, CDCl
3) δ 9.55 (s, 1H), 7.13 (d, J=9.0Hz, 2H), 6.51 (d, J=9.0Hz, 2H), 5.74-5.48 (m, 1H), 5.07 (brs, 1H), 5.04-5.02 (m, 1H), 3.60-3.39 (m, 2H), 2.88 (dd, J=14.5,6.4Hz, 1H), 2.60 (dd, J=14.5,8.3Hz, 1H), 2.18-1.96 (m, 4H);
13c NMR (100MHz, CDCl
3) δ 203.3,144.1,132.8,129.1,122.2,119.2,114.0,72.0,50.8,34.8,34.1,23.3; HRMS (ESI) m/z theoretical value for C
14h
17clNO
+[M+H]
+250.0993, measured value 250.0985.
2e: yellow oil, 45%;
1h NMR (400MHz, CDCl
3) δ 9.55 (s, 1H), 7.07 (t, J=8.1Hz, 1H), 6.69 (dd, J=7.8,1.3Hz, 1H), 6.58 (t, J=2.2Hz, 1H), 6.44 (dd, J=8.4,2.5Hz, 1H), 5.72-5.54 (m, 1H), 5.09-5.07 (m, 1H), 5.06-5.03 (m, 1H), 3.60-3.51 (m, 1H), 3.51-3.43 (m, 1H), 2.90 (dd, J=14.5,6.4Hz, 1H), 2.62 (dd, J=14.5,8.4Hz, 1H), 2.16-1.98 (m, 4H);
13c NMR (100MHz, CDCl
3) δ 203.2,146.6,135.2,132.7,130.2,119.3,117.2,112.9,111.0,72.1,50.7,34.9,34.2,23.2; HRMS (ESI) m/z theoretical value for C
14h
17clNO
+[M+H]
+250.0993, measured value 250.0988.
2f: yellow oil, 46%; 1H NMR (400MHz, CDCl
3) δ 9.60 (s, 1H), 7.24 – 7.15 (m, 2H), 6.73 (t, J=7.3Hz, 1H), 6.62 (d, J=8.1Hz, 2H), 5.06-4.92 (m, 1H), 3.62 – 3.54 (m, 1H), 3.52 – 3.47 (m, 1H), 2.78 (dd, J=15.0,6.6Hz, 1H), 2.67 (dd, J=15.0,8.5Hz, 1H), 2.11 – 1.98 (m, 4H), 1.65 (s, 3H), 1.51 (s, 3H); 13CNMR (100MHz, CDCl
3) δ 204.4,145.4,135.0,129.4,118.5,117.4,113.1,72.9,50.6,34.1,29.0,26.1,23.4,18.0; HRMS (ESI) m/z theoretical value for C
16h
22nO
+[M+H]
+244.1696, measured value 244.1687.
2g: yellow oil, 65%; 1H NMR (400MHz, CDCl
3) δ 9.44 (s, 1H), 7.25 – 7.17 (m, 2H), 6.74 (t, J=7.3Hz, 1H), 6.56 (d, J=8.1Hz, 2H), 5.54 (d, J=6.8Hz, 2H), 3.74 – 3.63 (m, 1H), 3.61 – 3.55 (m, 1H), 3.43 (d, J=15.1Hz, 1H), 3.11 (d, J=15.1Hz, 1H), 2.40 – 2.24 (m, 2H), 2.17 – 2.03 (m, 2H);
13c NMR (100MHz, CDCl
3) δ 203.1,145.0,129.6,128.0,122.1,117.3,112.6,72.3,50.5,40.1,33.3,23.3; HRMS (ESI) m/z theoretical value for C
14h1
7brNO
+[M+H]
+294.0488, measured value 294.0485.
2h: yellow oil, 63%;
1h NMR (400MHz, CDCl
3) δ 9.46 (s, 1H), 6.81 (d, J=9.1Hz, 2H), 6.61 (d, J=7.1Hz, 2H), 5.26 (s, 1H), 5.09 (s, 1H), 3.75 (s, 3H), 3.67-3.59 (m, 1H), 3.55 (dd, J=15.5,7.6Hz, 1H), 3.29 (d, J=14.8Hz, 1H), 2.96 (d, J=14.9Hz, 1H), 2.40-2.21 (m, 2H), 2.21-2.03 (m, 2H);
13c NMR (125MHz, CDCl
3) δ 203.3,138.1,117.3,115.1,113.8,72.0,55.8,50.7,38.3,33.3,23.3; HRMS (ESI) m/z theoretical value for C
15h
19clNO
2 +[M+H]
+280.1099, measured value 280.1085.
2i: yellow oil, 64%;
1h NMR (400MHz, CDCl
3) δ 9.55 (s, 0.36H), 9.51 (s, 0.59H), 6.83 – 6.75 (m, 2H), 6.71 – 6.66 (m, 2H), 5.95 – 5.87 (m, 0.36H), 5.64 – 5.47 (m, 0.63H), 5.17 – 5.03 (m, 0.76H), 4.95 (dt, J=10.6,1.5Hz, 0.64H), 4.86 (dt, J=17.4,1.5Hz, 0.63H), 3.74 (s, 3H), 3.59 – 3.29 (m, 3H), 2.19 – 1.88 (m, 4H), 1.05 (d, J=6.7Hz, 1H), 0.78 (d, J=6.9Hz, 1.14H);
13c NMR (100MHz, CDCl
3) δ 200.8,200.0,152.2,139.5,138.1,134.0,116.1,115.7,115.1,114.9,114.7,114.6,73.5,55.7,51.3,51.1,36.1,34.4,30.3,30.0,23.4,23.3,14.0,12.5; HRMS (ESI) m/z theoretical value for C
16h
22nO
2 +[M+H]
+260.1645, measured value 260.1639.
Claims (7)
1. a synthetic method for 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin, is characterized in that carrying out according to following step:
1-alkylsulfonyl triazole 1, metal catalyst are blended in a kind of organic solvent and stir by a certain percentage, and according to substrate and specificity of reagent, temperature controls between certain temperature, after certain hour, stopped reaction, adds proper amount of methanol, salt of wormwood and a small amount of water, stirring is spent the night;
With organic solvent ethyl acetate or dichloromethane extraction three times, with saturated common salt washing after organic phase merges, then use anhydrous sodium sulfate drying, remove solvent under reduced pressure, residue with Ethyl acetate and sherwood oil are eluent, silica gel column chromatogram separating purification, obtain corresponding nitrogen heterocyclic aldehyde 2;
Or remove organic solvent under reduced pressure after having reacted, the direct silica gel chromatographic column of residue is separated.
2. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, is characterized in that the structural formula of wherein said 1-alkylsulfonyl triazole 1 is
, wherein R
1for various substituting group (be specially neighbour, to methoxyl group, alkyl, halogen etc.); R
2for the alkyl (being specially methyl, ethyl, benzyl etc.), various fat base (being specially methyl esters, ethyl ester etc.), various halogen (being specially chlorine, bromine, fluorine) etc. of the aryl (being specially phenyl, p-methylphenyl etc.) of various replacement, various replacement; R
3for various alkyl, the aryl etc. of various replacement.
3. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, is characterized in that wherein said solvent is the non-polar solvents such as tetrahydrofuran (THF), toluene, methylene dichloride, trichloromethane, 1,2-methylene dichloride.
4. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, is characterized in that wherein said 1-alkylsulfonyl triazole 1, catalyst molar ratio is between 1.0:0.005 to 1.0:0.05.
5. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, it is characterized in that wherein said catalyzer is rhodium compound and the trifluoromethanesulfonic acids such as rhodium acetate, rhodium caprylate, m-phthalic acid rhodium, the silver salt such as copper compound and silver trifluoromethanesulfonate such as trifluoracetic acid copper.
6. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, is characterized in that wherein said temperature of reaction is between 50-120 degree.
7. the synthetic method of a kind of 2-allyl group-2-carboxaldehyde radicals-N-phenyl pyrroles Lin according to claim 1, is characterized in that the wherein said reaction times is between 10 minutes to 5 hours.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1953962A (en) * | 2004-04-19 | 2007-04-25 | 默克公司 | A process for the preparation of 2,2-disubstituted pyrroles |
| US20120190854A1 (en) * | 2007-10-12 | 2012-07-26 | The Board Of Trustees Of The University Of Illinois | Hydroamination of Alkenes |
| WO2014150639A1 (en) * | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | Process for preparing beta 3 agonists and intermediates |
-
2014
- 2014-12-12 CN CN201410766280.7A patent/CN104496875B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1953962A (en) * | 2004-04-19 | 2007-04-25 | 默克公司 | A process for the preparation of 2,2-disubstituted pyrroles |
| US20120190854A1 (en) * | 2007-10-12 | 2012-07-26 | The Board Of Trustees Of The University Of Illinois | Hydroamination of Alkenes |
| WO2014150639A1 (en) * | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | Process for preparing beta 3 agonists and intermediates |
Non-Patent Citations (3)
| Title |
|---|
| CHANGCHENG JING等: "Diversity-Oriented Three-Component Reactions of Diazo Compounds with Anilines and 4-Oxo-Enoates", 《ANGEWANDTE CHEMIE》 * |
| 孟倩等: "过渡金属催化N-磺酰基取代的杂环化合物的合成研究进展", 《浙江化工》 * |
| 邵志高等: "《实用调剂学》", 30 November 2013, 东南大学出版社 * |
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Effective date of registration: 20230803 Address after: Unit A601, No. 199, Tianfu 3rd Street, Chengdu Hi tech Zone, China (Sichuan) Pilot Free Trade Zone, Chengdu 610000, Sichuan Patentee after: Chengdu Rongchuang Yiheng Biomedical Technology Co.,Ltd. Address before: Gehu Lake Road Wujin District 213164 Jiangsu city of Changzhou province No. 1 Patentee before: CHANGZHOU University |
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