CN107353294A - A kind of method that multi-component reaction of catalysis of iodine prepares indoles volution compound - Google Patents

A kind of method that multi-component reaction of catalysis of iodine prepares indoles volution compound Download PDF

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Publication number
CN107353294A
CN107353294A CN201710540957.9A CN201710540957A CN107353294A CN 107353294 A CN107353294 A CN 107353294A CN 201710540957 A CN201710540957 A CN 201710540957A CN 107353294 A CN107353294 A CN 107353294A
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catalysis
reaction
iodine
component reaction
compound
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张敏
杨文博
钱敏
刘莉
赵婷
仰榴青
吴向阳
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Jiangsu University
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Jiangsu University
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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
    • C07D491/12—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 three hetero rings
    • C07D491/20—Spiro-condensed systems

Abstract

The invention belongs to technical field of medical intermediate preparation, and in particular to a kind of multi-component reaction of catalysis of iodine prepares the new method of indoles volution compound.The present invention is raw material with Isatine derivatives, 1,3 dicarbonyl compounds and 4 Hydroxycoumarins and its derivative, and iodine is catalyst, and raw material used in reaction is easy to get, operation is easy, and the compound generated can be used as drug candidate, there is potential application value.

Description

A kind of method that multi-component reaction of catalysis of iodine prepares indoles volution compound
Technical field
The invention belongs to pharmaceutical intermediate preparing technical field, and in particular to a kind of multi-component reaction of catalysis of iodine prepares Yin The new method of diindyl volution compound.
Background technology
Indoles spiro-compound is the core texture of many medicines and natural alkaloid, and there is extensive biology and pharmacology to live Property.Such as all containing indoles spirane structure in the medicine such as strychnia, cyclopamine and NITD 609, wherein strychnia can conduct Central nervous excitation agent；Cyclopamine is a kind of Hedgehog signal pathway inhibitors, can suppress protein active；And NITD 609 is A kind of anti-malarial drug candidate well.
Catalytic way used is mostly Protic Acid Catalyzed in the method for current synthesis of indole volution compound, organic catalysis and Metal catalytic etc., is often accompanied by that poor for applicability, side reaction is more, aftertreatment technology is complicated, etching apparatus, pollution environment etc. is obvious lacks Point.The present invention is first catalyst using iodine, with Isatine derivatives, 1,3- dicarbonyl compounds and 4 hydroxy coumarin and Its derivative is that three component reactions of raw material progress prepare indoles volution compound.
The content of the invention
In view of the deficienciess of the prior art, the invention provides one kind to utilize simple substance catalysis of iodine Isatine derivatives, 1,3- Dicarbonyl compound and 4 hydroxy coumarin and its derivative carry out the new of three component reaction synthesis of indole volution compounds (I) Method.Reaction equation is as follows：
Wherein：R1For H, halogen, alkyl, alkoxy or nitro；R2For alkyl；R3For H or alkyl；R4For H or alkyl；R5For H, halogen, alkyl or alkoxy；N is 0 or 1.
The present invention is to realize above-mentioned purpose by following technological means.
Isatine derivatives, 1,3- dicarbonyl compounds and 4 hydroxy coumarin and its derivative are dissolved in proportion organic In solvent, catalyst simple substance iodine is added, at a certain temperature, after reacting a period of time, TLC detections, it is determined that reaction has terminated, is revolved Turn evaporation of solvent, concentrate obtains white or light yellow solid powder, as the compounds of this invention (I) using column chromatography.
The ratio between the Isatine derivatives, 1,3- dicarbonyl compounds and amount of 4 hydroxy coumarin and its derivative material are 1:1:1。
In such scheme, the dosage of iodine is the 5%-20% of the amount of Isatine derivatives material；
Described organic solvent is one in methanol, dichloromethane, chloroform, 1,2- dichloroethanes, DMF, DMSO or acetonitrile Kind；
The reaction temperature is 50~80 DEG C；Reaction time is 24~48h；
Stationary phase used in the column chromatography is the column layer chromatography silicone rubber of 200-300 mesh, and mobile phase is that boiling range is 60~90 DEG C petroleum ether and ethyl acetate mixed liquor.
The beneficial effects of the invention are as follows：
Using iodine as catalyst, there is cheap and easy to get, mild condition, high catalytic efficiency, developed synthesis Yin The new method of diindyl spiro-compound.Raw material used in reaction is easy to get, operation is easy, the chemical combination of the formula (I) generated Thing is bioactive molecule, can have potential application value as the candidate compound of medicine.
Embodiment
The substantial feature of the present invention can emerge from from following embodiments, but it is not construed as protecting the present invention Protect any restrictions of scope.
Embodiment 1：
Accurately weigh 0.1611g N-methyl-isatins, 0.1121g hydroresorcinols, 0.1621g 4 hydroxy coumarins And 0.0254gI2It is dissolved in 4mL ClCH2CH2In Cl, at 60 DEG C after magnetic agitation 24h, TLC detections, it is determined that reaction has been tied Beam, rotary evaporation remove solvent, a of white solid I are obtained using column chromatography.Yield 82%, m.p.320.5~321.2 DEG C；1H NMR(400MHz,CDCl3)δ:7.88 (d, J=7.9Hz, 1H), 7.61~7.56 (m, 1H), 7.36 (t, J=7.6Hz, 1H), 7.28 (d, J=8.1Hz, 2H), 6.96~6.92 (m, 2H), 6.88 (d, J=7.7Hz, 1H), 3.38 (s, 3H), 2.86~ 2.83 (m, 2H), 2.46~2.31 (m, 2H), 2.18~2.02 (m, 2H)；13C NMR(100MHz,CDCl3)δ:195.1, 176.7,164.9,158.5,154.8,152.6,145.6,132.9,132.1,129.1,124.4,122.7,122.6, 122.1,116.8,114.6,113.1,107.9,104.5,46.0,37.1,27.6,26.9,20.0.Anal.Calcd for C24H17NO5:C 72.17,H 4.29,N 3.51；Found:C 72.37,H 4.51,N 3.40.
Embodiment 2：
Accurately weigh 0.2373g N- benzyls isatin, 0.1121g hydroresorcinols, 0.1621g 4 hydroxy coumarins And 0.0254gI2It is dissolved in 4mL DMF, at 70 DEG C after magnetic agitation 36h, TLC detections, it is determined that reaction has terminated, rotates Evaporation of solvent, the b of white solid I, yield 83%, m.p.306.9~307.1 DEG C are obtained using column chromatography；1H NMR (400MHz,DMSO-d6)δ:8.04 (d, J=7.8, Hz, 1H), 7.76 (t, J=7.8Hz, 1H), 7.63 (d, J=7.5Hz, 2H), 7.52 (t, J=7.7Hz, 1H), 7.47 (d, J=8.2Hz, 1H), 7.36 (t, J=7.5Hz, 2H), 7.28 (t, J= 7.3Hz, 1H), 7.12 (t, J=8.1Hz, 1H), 6.88 (t, J=7.4Hz, 1H), 6.64 (d, J=7.8Hz, 1H), 4.97 (ABd, J=16.4Hz, 1H), 4.92 (ABd, J=16.4Hz, 1H), 2.96~2.93 (m, 2H), 2.42~2.26 (m, 2H), 2.05~1.95 (m, 2H)；13C NMR(100MHz,DMSO-d6)δ:195.8,176.8,166.2,158.6,155.1,152.3, 145.2,137.0,134.1,132.6,128.9,128.8,127.8,127.5,125.5,123.9,123.6,122.4, 117.0,113.9,112.9,108.7,104.1,45.9,44.7,37.3,27.4,20.1.Anal.Calcd for C30H21NO5:C 75.78,H 4.45,N 2.95；Found:C 75.61,H 4.73,N 3.22.
Embodiment 3：
It is accurate to weigh the bromo- N-methyl-isatins of 0.2401g 5-, 0.0981g 1,3- cyclopentanediones, 0.1621g 4- hydroxyls perfume Legumin and 0.0508g I2It is dissolved in 4mL CH2Cl2In, at 60 DEG C after magnetic agitation 24h, TLC detections, it is determined that reaction has been tied Beam, rotary evaporation remove solvent, the c of white solid I, yield 79%, m.p.315.1~315.4 DEG C are obtained using column chromatography；1H NMR(400MHz,DMSO-d6)δ:8.07 (dd, J=7.9,1.3Hz, 1H), 7.82~7.77 (m, 1H), 7.57~7.52 (m, 2H), 7.50~7.47 (m, 2H), 7.05 (d, J=8.8Hz, 1H), 3.21 (s, 3H), 3.03~3.00 (m, 2H), 2.50~ 2.47(m,2H)；13C NMR(100MHz,DMSO-d6)δ:200.5,177.6,174.7,159.2,157.6,152.5,144.5, 134.3,133.6,132.1,127.3,125.6,123.6,117.1,116.5,114.5,113.3,110.4,103.3,46.1, 33.9,27.1,25.5.Anal.Calcd for C23H14BrNO5:C 59.50,H 3.04,N 3.02；Found:C 59.56,H 3.03,N 2.81.
Embodiment 4：
Accurately weigh 0.1872g N- pi-allyls isatin, 0.1402g 5,5- dimethyl-hydroresorcinol, 0.1621g 4 hydroxy coumarin and 0.0254g I2It is dissolved in 4mL CH3In CN, at 50 DEG C after magnetic agitation 24h, TLC detections, it is determined that instead It should terminate, rotary evaporation removes solvent, and the d of white solid I, yield 86%, m.p.232.1~232.5 are obtained using column chromatography ℃；1H NMR(400MHz,DMSO-d6)δ:8.00 (dd, J=8.0,1.4Hz, 1H), 7.77~7.73 (m, 1H), 7.51 (t, J =7.6Hz, 1H), 7.45 (d, J=8.2Hz, 1H), 7.21 (td, J=7.7,1.2Hz, 1H), 7.13 (d, J=7.0Hz, 1H), 6.91~6.86 (m, 2H), 5.98~5.89 (m, 1H), 5.62 (dd, J=17.3,1.7Hz, 1H), 5.22 (dd, J=10.4, 1.6Hz, 1H), 4.43~4.30 (m, 2H), 2.84 (q, J=17.6Hz, 2H), 2.29 (d, J=16.0Hz, 1H), 2.15 (d, J =16.0Hz, 1H), 1.09 (s, 3H), 1.03 (s, 3H)；13C NMR(100MHz,DMSO-d6)δ:195.5,176.1,164.3, 158.5,155.2,152.3,145.0,134.1,132.7,132.5,129.0,125.5,123.6,123.5,122.3, 117.5,116.9,112.9,112.8,108.8,104.0,50.8,45.8,43.1,32.3,28.2,27.3.Anal.Calcd for C28H23NO5:C 74.16,H 5.11,N 3.09；Found:C 74.41,H 5.00,N 2.88.
Embodiment 5：
Accurately weigh 0.1872g N- pi-allyls isatin, 0.1121g hydroresorcinols, 0.1966g 6- chloro-4-hydroxyls Cumarin and 0.0127g I2It is dissolved in 4mL ClCH2CH2In Cl, at 60 DEG C after magnetic agitation 48h, TLC detections, it is determined that instead It should terminate, rotary evaporation removes solvent, and the e of white solid I, yield 72%, m.p.245.1~245.7 are obtained using column chromatography ℃；1H NMR(400MHz,DMSO-d6)δ:8.04 (d, J=2.4Hz, 1H), 7.78 (dd, J=8.9,2.4Hz, 1H), 7.49 (d, J=8.8Hz, 1H), 7.21 (t, J=7.6Hz, 1H), 7.13 (d, J=7.3Hz, 1H), 6.91~6.86 (m, 2H), 5.98 ~5.88 (m, 1H), 5.61 (d, J=16.9Hz, 1H), 5.22 (d, J=10.7Hz, 1H), 4.40~4.29 (m, 2H), 2.93 (t, J=5.9Hz, 2H), 2.39~2.23 (m, 2H), 2.04~1.93 (m, 2H)；13C NMR(100MHz,DMSO-d6)δ: 195.6,176.0,166.1,158.1,154.1,150.9,145.0,133.7,132.7,129.5,129.0,123.9, 122.8,122.3,119.1,117.5,114.4,113.8,108.7,104.8,92.2,45.9,43.1,37.2,27.2, 20.1.Anal.Calcd for C26H18ClNO5:C 67.91,H3.95,N 3.05；Found:C 67.64,H 3.82,N 3.23.
Embodiment 6：
Accurately weigh 0.1912g N- methyl -5- methoxyl groups isatin, 0.1121g hydroresorcinols, 0.1621g 4- hydroxyls Butylcoumariii and 0.0254g I2It is dissolved in 4mL ClCH2CH2In Cl, at 60 DEG C after magnetic agitation 24h, TLC detections, it is determined that Reaction has terminated, and rotary evaporation removes solvent, and the f of light yellow solid I is obtained using column chromatography, yield 64%, and m.p.251.8~ 252.1℃；1H NMR(400MHz,CDCl3)δ:7.88 (d, J=7.7Hz, 1H), 7.59 (t, J=7.8Hz, 1H), 7.36 (t, J =7.5Hz, 1H), 7.29 (d, J=8.3Hz, 1H), 6.79 (s, 2H), 6.56 (s, 1H), 3.70 (s, 3H), 3.35 (s, 3H), 2.86~2.83 (m, 2H) .2.46~2.32 (m, 2H), 2.18~2.04 (m, 2H)；13C NMR(100MHz,CDCl3)δ: 195.1,176.6,164.9,158.4,155.7,154.8,152.6,139.4,133.4,132.9,124.4,122.7, 116.8,114.5,113.0,112.3,111.3,108.0,104.4,55.7,46.3,37.1,27.6,27.0, 20.0.Anal.Calcd for C25H19NO6:C 69.92,H 4.46,N 3.26；Found:C 69.71,H 4.73,N 3.52.
Embodiment 7：
Accurately weigh 0.1752g N- methyl -5- methylisatins, 0.1121g hydroresorcinols, 0.1621g 4- hydroxyls Cumarin and 0.0254g I2It is dissolved in 4mL CHCl3In, at 60 DEG C after magnetic agitation 36h, TLC detections, it is determined that reaction has been tied Beam, rotary evaporation remove solvent, the g of light yellow solid I, yield 61%, m.p.337.5~338.1 DEG C are obtained using column chromatography；1H NMR(400MHz,DMSO-d6)δ；8.06 (dd, J=7.9,1.3Hz, 1H), 7.81~7.76 (m, 1H), 7.56~7.50 (m, 2H), 7.09 (d, J=7.9Hz, 1H), 6.99 (s, 1H), 6.93 (d, J=7.9Hz, 1H), 3.19 (s, 3H), 3.03~3.01 (m, 2H), 2.48~2.45 (m, 2H) .2.18 (s, 3H)；13C NMR(100MHz,DMSO-d6)δ:200.4,177.2,174.9, 159.0,157.1,152.4,142.8,134.2,131.7,131.5,129.6,125.6,124.8,123.5,117.2, 117.1,113.2,108.2,104.0,46.1,33.9,27.0,25.4,21.0.Anal.Calcd for C24H17NO5:C 72.17,H 4.29,N 3.51；Found:C72.29,H 4.07,N 3.64.
Embodiment 8：
Accurately weigh 0.2062g N- methyl-5-nitros isatin, 0.1121g hydroresorcinols, 0.1621g 4- hydroxyls Cumarin and 0.0254g I2It is dissolved in 4mL CH2Cl2In, at 60 DEG C after magnetic agitation 36h, TLC detections, it is determined that reaction is Terminate, rotary evaporation removes solvent, and the h of light yellow solid I, yield 72%, m.p.280.9~281.1 DEG C are obtained using column chromatography ；1H NMR(400MHz,DMSO-d6)δ:8.31~8.27 (m, 2H), 8.10 (d, J=8.1Hz, 1H), 7.81 (t, J=7.7Hz, 1H), 7.58~7.52 (m, 2H), 7.34 (d, J=8.6Hz, 1H), 3.32 (s, 3H), 3.07~3.04 (m, 2H), 2.51~ 2.49(m,2H)；13C NMR(100MHz,DMSO-d6)δ:200.7,178.1,175.8,159.5,158.0,152.5,151.0, 143.3,134.4,132.1,126.8,125.7,123.7,120.4,117.2,116.0,113.4,108.7,102.8,45.9, 33.9,27.5,25.6.Anal.Calcd for C23H14N2O7:C 64.19,H 3.28,N 6.51.Found:C 64.03,H 3.07,N 6.62。

Claims (7)

1. a kind of method that multi-component reaction of catalysis of iodine prepares indoles volution compound, it is characterised in that：In proportion by indigo Red derivative, 1,3- dicarbonyl compounds and 4 hydroxy coumarin and its derivative are dissolved in organic solvent, add catalyst Iodine, at a certain temperature, after reacting a period of time, TLC detections, it is determined that reaction has terminated, rotary evaporation removes solvent, dense Contracting thing obtains white or light yellow solid powder, i.e. compound (I) using column chromatography, and reaction equation is as follows：
Wherein：R1For H, halogen, alkyl, alkoxy or nitro；R2For alkyl；R3For H or alkyl；R4For H or alkyl；R5For H, halogen Element, alkyl or alkoxy；N is 0 or 1.
2. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 prepares indoles volution compound, its It is characterised by：The ratio between the Isatine derivatives, 1,3- dicarbonyl compounds and amount of 4 hydroxy coumarin and its derivative material For 1:1:1.
3. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 or 2 prepares indoles volution compound, It is characterized in that：The dosage of the iodine is the 5-20% of the amount of Isatine derivatives material.
4. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 prepares indoles volution compound, its It is characterised by：Organic solvent used is one in methanol, dichloromethane, chloroform, 1,2- dichloroethanes, DMF, DMSO or acetonitrile Kind.
5. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 prepares indoles volution compound, its It is characterised by：The reaction temperature is 50~80 DEG C.
6. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 prepares indoles volution compound, its It is characterised by：The reaction time is 24~48h.
7. the method that a kind of multi-component reaction of catalysis of iodine according to claim 1 prepares indoles volution compound, its It is characterised by：Stationary phase used in the column chromatography is the column layer chromatography silicone rubber of 200-300 mesh, and mobile phase is that boiling range is 60~90 DEG C petroleum ether and ethyl acetate mixed liquor.
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Cited By (3)

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CN109666031A (en) * 2018-11-02 2019-04-23 江苏大学 A kind of spiro indole quinoline ketone compounds and the preparation method and application thereof
CN112898311A (en) * 2021-01-29 2021-06-04 江苏大学 Indole spiro pyridocoumarin compound and preparation method and application thereof
CN113943309A (en) * 2021-09-18 2022-01-18 江苏大学 Indole spiro [ benzofuran-2, 2' -pyrrolidine ] compound, preparation method thereof and application thereof in preventing and treating plant viruses

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109666031A (en) * 2018-11-02 2019-04-23 江苏大学 A kind of spiro indole quinoline ketone compounds and the preparation method and application thereof
CN112898311A (en) * 2021-01-29 2021-06-04 江苏大学 Indole spiro pyridocoumarin compound and preparation method and application thereof
CN112898311B (en) * 2021-01-29 2022-06-21 江苏大学 Indole spiro pyridocoumarin compound and preparation method and application thereof
CN113943309A (en) * 2021-09-18 2022-01-18 江苏大学 Indole spiro [ benzofuran-2, 2' -pyrrolidine ] compound, preparation method thereof and application thereof in preventing and treating plant viruses
CN113943309B (en) * 2021-09-18 2023-11-10 江苏大学 Indolospiro [ benzofuran-2, 2' -pyrrolidine ] compound, preparation method thereof and application thereof in preventing and treating plant viruses

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Application publication date: 20171117