CN108358826B - Synthesis method of tetrahydroindole - Google Patents
Synthesis method of tetrahydroindole Download PDFInfo
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- CN108358826B CN108358826B CN201810262487.9A CN201810262487A CN108358826B CN 108358826 B CN108358826 B CN 108358826B CN 201810262487 A CN201810262487 A CN 201810262487A CN 108358826 B CN108358826 B CN 108358826B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
The invention relates to a method for synthesizing tetrahydroindole, which takes diene sulfonamide, alkyne bromide, copper sulfate pentahydrate, potassium carbonate and 1,10 phenanthroline as raw materials, and the required tetrahydroindole is prepared by a two-step one-pot method after heating reaction overnight. The invention has the beneficial effects that: the preparation of reaction raw materials is convenient, the catalyst is cheap, the reaction operation is simple and convenient, and the product obtained by the one-pot method is quick and easy to obtain.
Description
Technical Field
The invention belongs to the technical field of chemical pharmacy and fine chemical preparation, and particularly relates to a method for synthesizing tetrahydroindole.
Background
Tetrahydroindoles are an important class of organic compounds, and compounds having this fragment are ubiquitous in some natural products and artificial chemicals, particularly in some molecules having biological activity. The preparation of such compounds reported in the literature at present is summarized by the following equation:
the diene alkyne sulfamide is used as a starting material, and the tetrahydro indole can be obtained by heating and cyclization in solvent benzene, but the solvent benzene has high toxicity and cannot be industrialized. Or the tetrahydro indole is obtained by cyclization at room temperature under the catalysis of metal rhodium and silver compounds, but the rhodium catalyst is expensive. And the two methods need to separately prepare the substrate diene alkyne sulfamide, and the synthesis steps are long.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: based on the problems of long synthesis steps and expensive catalyst, the invention provides a cheap tetrahydroindole two-step one-pot synthesis method.
The technical scheme adopted by the invention for solving the technical problems is as follows: a method for synthesizing tetrahydroindole, which comprises the following steps: under the protection of nitrogen, mixing and dissolving diene sulfonamide, alkyne bromine, a catalyst, alkali and a ligand in a solvent, heating for reaction, carrying out reduced pressure distillation to remove the solvent, and separating and purifying residues by silica gel column chromatography by using ethyl acetate and petroleum ether as eluent to obtain the tetrahydroindole.
The synthetic route of the invention is as follows:
diene sulfonamide 1 and alkyne bromide 2 generate eneyne I in a solvent under the action of a catalyst, alkali and a ligand, the eneyne I is directly cyclized in a system without any treatment to obtain a tetrahydroindole product 3, and the preparation of the tetrahydroindole by a two-step one-pot reaction is realized.
Further, the general structural formula of the diene sulfonamide 1 is as follows:
wherein R is1Is alkyl and aryl, in particular n-butyl, phenyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, m-bromophenyl, 2-furyl.
The preparation method of the diene sulfonamide 1 comprises the following steps:
the enal (10mmol) was dissolved in tetrahydrofuran, cyclopropene magnesium bromide (30mL, 1M in tetrahydrofuran) was injected, the reaction was stirred at room temperature for 3 hours, and diethyl phosphite (1.66g, 12mmol) was added to the reaction and stirring at room temperature was continued for 5 hours. After the reaction is finished, the reaction solution is quenched by dilute hydrochloric acid, extracted by ethyl acetate and dried by anhydrous sodium sulfate. And (4) spin-drying the solvent by using a rotary evaporator, and performing column chromatography purification to obtain S1 with the yield of 50-65%. Dissolving S1 in DMF, adding sodium azide (1.5 equivalent), vacuumizing and changing nitrogen, carrying out oil bath at 80 ℃ overnight, adding a large amount of water after the reaction is finished, extracting with ethyl acetate, drying with anhydrous sodium sulfate, and carrying out rotary evaporation on a rotary evaporator without purification directly for the next step. Taking one dry round-bottom flask, adding lithium aluminum hydride (1 equivalent), vacuumizing for changing nitrogen, adding anhydrous tetrahydrofuran, placing the reaction in an ice bath, dropwise adding the product obtained in the previous step, removing the ice bath after dropwise adding, stirring at room temperature for 2 hours, finishing the reaction, quenching with water and an aqueous solution of sodium hydroxide, extracting with ethyl acetate, drying with anhydrous sodium sulfate, and performing spin drying without purification directly on the next step. Dissolving the product in dichloromethane, vacuumizing and exchanging nitrogen, adding triethylamine (1.4 equivalents), stirring at room temperature for 1 hour, dissolving p-toluenesulfonyl chloride in dichloromethane, slowly dropwise adding into the reaction, continuing to stir at room temperature for 1 hour, adding a sodium bicarbonate solution after the reaction is finished, quenching, extracting with dichloromethane, drying with anhydrous sodium sulfate, and performing spin-drying on a column to obtain the diene sulfonamide 1 with the yield of 64-75%.
Further, the general structural formula of the alkyne bromide is:
wherein R is2Is alkyl, aryl, substituted carbonyl, specifically n-hexyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, m-bromophenyl, 2-furyl, 2-thienyl, p-chlorophenyl, thienyl, methoxycarbonyl (CH)3OCO-)。
Further, the catalyst is copper sulfate pentahydrate.
Further, the base is potassium carbonate.
Further, the ligand is 1,10 phenanthroline.
Further, the solvent is an aprotic solvent, toluene.
Further, the molar ratio of the diene sulfonamide to the alkyne bromide to the catalyst to the base to the ligand is 1: 1-1.5: 0.1: 1-3: 0.2.
Further, the reaction temperature is 50-120 ℃, and the reaction time is 5-12 hours.
The invention takes diene sulfonamide as raw material for the first time, and adopts one-pot operation; the screened catalyst and ligand are cheap, and the one-pot yield is highest. The invention has the beneficial effects that: diene alkyne sulfonamide and alkyne bromide are generated on site under the action of cheap and easily available catalysts of copper sulfate pentahydrate and ligands of 1,10 phenanthroline, and are heated to react to prepare the required tetrahydroindole by a two-step one-pot method. The preparation of reaction raw materials is convenient, the catalyst is cheap, the reaction operation is simple and convenient, and the product obtained by the one-pot method is quick and easy to obtain.
Detailed Description
The invention will now be further illustrated by reference to specific examples, which are intended to be illustrative of the invention and are not intended to be a further limitation of the invention.
The reagent used in the invention is prepared by reference to relevant documents, and the solvent is purified and refined.
Example 1
Taking 10mL of a sealed tube, weighing 1a 65mg (1 equivalent), 2a 47mg (1.3 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (55mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 80 ℃ for 10 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography separation and purification using petroleum ether and ethyl acetate as eluents to give colorless liquid 3aa in a yield of 85%.1H NMR(300MHz,CDCl3)δ7.44(d,J＝8.3Hz,2H),7.18(d,J＝8.0Hz,2H),7.08–7.04(m,6H),7.01–6.94(m,4H)5.78–5.68(m,2H),4.60(dt,J＝9.1,2.0Hz,1H),3.74–3.64(m,1H),3.57(td,J＝9.1,1.4Hz,1H),2.52–2.42(m,1H),2.39(s,3H),2.31–2.21(m,1H),1.74–1.60(m,1H).13C NMR(75MHz,CDCl3) δ 143.3,142.9,138.9,135.3,135.0,130.6,129.4,129.2,129.0,128.9,128.0,127.5,127.5,126.1,126.0,122.9,48.8,48.4,38.5,29.6,21.6 HRMS (ESI) m/z theoretical value C27H26NO2S+[M+H]+428.1679, found 428.1682.
Example 2
Taking 10mL of a sealed tube, weighing 1b 61mg (1 equivalent), 2a 36mg (1 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (28mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 80 ℃ for 10 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as an eluent to give 3ba as a colorless liquid in a yield of 63%.1H NMR(400MHz,CDCl3)δ7.46(d,J＝7.8Hz,2H),7.35–7.23(m,5H),7.20(d,J＝7.9Hz,2H),5.69(dd,J＝22.1,10.4Hz,2H),3.63–3.49(m,3H),2.40(s,3H),2.34–2.24(m,1H),2.16–2.10(m,1H),1.56–1.43(m,1H),1.29–0.97(m,6H),0.70(t,J＝6.5Hz,3H).13C NMR(100MHz,CDCl3)δ143.3,139.0,135.3,135.0,130.5,130.0,129.4,128.6,127.9,127.5,126.4,124.2,48.2,40.1,38.6,32.1,29.5,26.6,22.7,21.6,13.9 HRMS (ESI) m/z theory C25H30NO2S+[M+H]+408.1992, found 408.1993.
Example 3
Taking 10mL of a sealed tube, weighing 1c 64mg (1 equivalent), 2a 54mg (1.5 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (83mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 80 ℃ for 10 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to separation and purification by silica gel column chromatography using petroleum ether and ethyl acetate as an eluent to give colorless liquid 3ca in 62% yield.1H NMR(300MHz,CDCl3)δ7.39(d,J＝8.3Hz,2H),7.18–7.12(m,6H),7.11–7.05(m,2H),6.02(dd,J＝3.1,1.9Hz,1H),5.85–5.80(m,1H),5.78–5.72(m,2H),4.74(dt,J＝9.6,2.3Hz,1H),3.73–3.64(m,1H),3.57–3.50(m,1H),2.55–2.42(m,1H),2.38(s,3H)2.27–2.17(m,1H),1.75–1.60(m,1H).13C NMR(75MHz,CDCl3) δ 155.05,143.23,141.14,138.61,135.41,135.24,129.36,128.61,127.51,127.45,127.42,127.06,126.29,124.72,109.96,107.16,48.38,42.20,38.39,29.09,21.57 hrms (esi) m/z theoretical value C25H24NO3S+[M+H]+418.1471, found 418.1469.
Example 4
Taking 10mL of a sealed tube, weighing 1a 65mg (1 equivalent), 2b 56mg (1.3 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (55mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 120 ℃ for 5 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as an eluent to give colorless liquid 3ab in 74% yield.1H NMR(400MHz,CDCl3)δ7.41(d,J＝8.2Hz,2H),7.18(d, J ═ 8.1Hz,2H), 7.09-7.05 (m,2H), 7.01-6.91 (m,7H),5.76(dt, J ═ 10.0,2.3Hz,1H),5.69(dt, J ═ 9.9,2.4Hz,1H),4.54(dt, J ═ 9.1,2.3Hz,1H), 3.81-3.73 (m,1H),3.60(t, J ═ 9.5Hz,1H), 2.57-2.48 (m,1H),2.40(s,3H), 2.31-2.25 (m,1H), 1.72-1.62 (m,1H), 13C NMR (100MHz, CDCl3) δ 143.47,142.58,137.31,135.84,135.60,131.69,130.50,130.26,129.41,128.88,128.16,127.68,127.61,127.18,126.28,122.89,48.61,48.55,38.66,29.54,21.61, 84, theoretical values (hrz/m) of C (z/m/z)27H24ClNNaO2S+[M+Na]+484.1108, found 484.1111.
Example 5
Taking 10mL of a sealed tube, weighing 1a 65mg (1 equivalent), 2c 40mg (1.3 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (55mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 50 ℃ for 12 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography separation and purification using petroleum ether and ethyl acetate as eluents to give colorless liquid 3ac in 49% yield.1H NMR(400MHz,CDCl3)δ7.62(d,J＝8.2Hz,2H),7.28–7.25(m,2H),7.16–7.12(m,2H),7.07–7.03(m,4H),6.78(dd,J＝3.5,0.9Hz,1H),6.71(dd,J＝5.0,3.6Hz,1H),5.69(t,J＝10.6Hz,2H),4.60(d,J＝8.8Hz,1H),3.67(dd,J＝9.5,4.7Hz,2H),2.43(s,3H),2.40–2.38(m,1H),2.26–2.19(m,1H),1.72–1.63(m,1H).13C NMR(100MHz,CDCl3) δ 143.6,143.1,140.1,136.9,134.9,130.6,129.5,128.7,128.1,127.8,126.8,126.2,125.8,124.4,122.9,122.1,49.4,48.5,38.7,29.4,21.6 HRMS (ESI) m/z theoretical value C25H24NO2S2+[M+H]+434.1243, found 434.1253.
Example 6
10mL of the tube was sealed, and 1a 65mg (1 equivalent), 2d 34mg (1.3 equivalent), copper sulfate pentahydrate (5mg) and potassium carbonate (55mg) were weighedmg),1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting for 6 hours at 100 ℃. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography using petroleum ether and ethyl acetate as an eluent to give 3ad as a colorless liquid in 59% yield.1H NMR(400MHz,CDCl3)δ7.72(d,J＝8.2Hz,2H),7.31–7.28(m,4H),7.24–7.12(m,3H),5.58–5.51(m,2H),4.21(d,J＝8.6Hz,1H),3.60–3.47(m,2H),2.75–2.69(m,1H),2.43(s,3H),2.03–1.97(m,1H),1.92–1.85(m,1H),1.52–1.36(m,4H),1.28–1.08(m,6H),0.82(t,J＝6.9Hz,3H).13C NMR(100MHz,CDCl3) δ 143.7,143.1,134.7,133.1,131.8,130.1,129.6,128.5,127.9,126.7,122.9,48.8,46.7,37.4,31.6,29.8,29.7,29.5,26.8,22.6,21.7,14.1 HRMS (ESI) m/z theoretical value C27H34NO2S+[M+H]+436.2305, found 436.2301.
Example 7
Taking 10mL of a sealed tube, weighing 1a 65mg (1 equivalent), 2e 46mg (1.3 equivalent), copper sulfate pentahydrate (5mg), potassium carbonate (55mg) and 1,10 phenanthroline (8mg), adding 2mL of toluene to dissolve the raw materials, vacuumizing and changing nitrogen, and reacting at 90 ℃ for 8 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography separation and purification using petroleum ether and ethyl acetate as eluents to give colorless liquid 3ae in a yield of 72%.1H NMR(400MHz,CDCl3)δ7.74(d,J＝8.2Hz,2H),7.31(d,J＝8.1Hz,2H),7.27–7.25(m,2H),7.21–7.18(m,3H)5.64(t,J＝11.2Hz,2H),4.50(d,J＝9.9Hz,1H),4.05–3.97(m,1H),3.94–3.86(m,1H),3.68(t,J＝9.3Hz,1H),3.43–3.36(m,1H),2.43(s,3H),2.38–2.30(m,1H),2.18–2.11(m,1H),1.73–1.63(m,1H),0.97(t,J＝7.1Hz,3H).13C NMR(100MHz,CDCl3) δ 167.0,144.1,142.1,139.0,134.2,130.5,129.7,128.9,128.3,127.9,126.9,122.2,119.7,60.3,49.2,45.6,38.7,28.6,21.7,13.8 HRMS (ESI) m/z theoretical value C24H26NO4S+[M+H]+424.1577 found 424.1574.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (5)
1. A method for synthesizing tetrahydroindole is characterized by comprising the following steps: the synthesis method comprises the following steps: under the protection of nitrogen, mixing and dissolving diene sulfonamide, alkyne bromine, a catalyst, alkali and a ligand in a solvent, heating for reaction, carrying out reduced pressure distillation to remove the solvent, and separating and purifying residues by silica gel column chromatography by using ethyl acetate and petroleum ether as an eluent to obtain tetrahydroindole;
the general structural formula of the diene sulfonamide is as follows:
wherein R is1Is alkyl or aryl;
the structural general formula of the alkyne bromide is as follows:
R2is alkyl, aryl, substituted carbonyl;
the catalyst is copper sulfate pentahydrate;
the alkali is potassium carbonate;
the ligand is 1,10 phenanthroline, and the solvent is a non-protonic solvent toluene.
2. The method for synthesizing tetrahydroindole according to claim 1, wherein: r in the structure of the diene sulfonamide1Is n-butyl, phenyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, m-bromophenyl, 2-furyl.
3. The method for synthesizing tetrahydroindole according to claim 1, wherein: r in the alkyne bromine structure2Is n-hexyl, pChlorophenyl, p-bromophenyl, p-methoxyphenyl, m-bromophenyl, 2-furyl, 2-thienyl, p-chlorophenyl, thienyl, methoxycarbonyl (CH)3OCO-)。
4. The method for synthesizing tetrahydroindole according to claim 1, wherein: the diene sulfonamide, the alkyne bromide, the catalyst, the alkali and the ligand are in a molar ratio of 1: 1-1.5: 0.1: 1-3: 0.2.
5. The method for synthesizing tetrahydroindole according to claim 1, wherein: the reaction temperature is 50-120 ℃, and the reaction time is 5-12 hours.
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