CN107141246A - A kind of preparation method of Isatine derivatives - Google Patents

A kind of preparation method of Isatine derivatives Download PDF

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CN107141246A
CN107141246A CN201710422389.2A CN201710422389A CN107141246A CN 107141246 A CN107141246 A CN 107141246A CN 201710422389 A CN201710422389 A CN 201710422389A CN 107141246 A CN107141246 A CN 107141246A
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alkyl
derivatives
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CN107141246B (en
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黄依铃
魏文廷
应炜炜
吴益
伍科玮
曹奕琦
汪依宁
朱立伟
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Ningbo University
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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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin

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  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

The invention discloses a kind of new method for synthesizing Isatine derivatives, this method uses nitrite tert-butyl/O2Catalytic oxidation system, without using metal reagent, react at normal temperatures and pressures, to obtain Isatine derivatives with purity in high yield, have the advantages that technological operation is simple and easy to apply, cost is low.

Description

A kind of preparation method of Isatine derivatives
Technical field
The present invention relates to a kind of preparation method of Isatine derivatives, more particularly to one kind is using 2- indolone derivatives as original Simple, the environment-friendly method for preparing Isatine derivatives of material, technique.
Background technology
Since Erdmann and Laurent in 1841 is by aoxidizing indigo (indigo), a kind of point has separately been obtained Son is C8H6NO2Organic compound, and it is named as indole dione (isatin, i.e. isatin), then finally determine to Kolbe Its structure, the chemical property and purposes of indole dione gradually by people cognition.Today, it has been found that indole dione skeleton Compound has extensive purposes in dyestuff, antibiotic, anticancer class medicine.Therefore, compound of the synthesis containing this kind of skeleton Also increasingly by the attention of synthetic organic chemists.
1841, Erdmann and Laurent were by experiment, and indigo (indigo) is initiation material, in various different oxidations Under the conditions of agent, indole dione is separately obtained, this is that mankind's first passage chemical method is obtained and found this organic Compound (formula one).
In recent years, some steps are simple, and the synthesis isatin approach of reaction condition gently is developed in succession.Wherein one Important channel is then that oxidation prepares corresponding Isatine derivatives by raw material of 2- indolone derivatives.
Yong-qiang Wang etc. (Tetrahedron Letters., 56 (2015), 1575-1580.) report substitution 2- oxindole compounds prepared under cupric, alkali, Oxygen Condition substitution isatin method (formula two).
Parvathaneni Sai Prathima etc. (Tetrahedron Letters., 56 (2015), 6385-6388.) It is then to report the side that a kind of substituted 2- indole ketone compounds oxidation under the conditions of PIDA, TEMPO prepares Isatine derivatives Method (formula three).
Inventor is by concentrating on studies, it is proposed that a kind of substituted 2- indole ketone compound oxidations prepare Isatine derivatives New method, this method has no report.
The content of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of technique is simple, cost is low, environment-friendly The new method of isatin-BETA-oxime derivative is prepared, using 2- indolone derivatives as raw material, under nitrite tert-butyl/Oxygen Condition Reaction prepares Isatine derivatives.
The preparation method for the Isatine derivatives that the present invention is provided, this method is using 2- indolone derivatives as raw material, under Row step is prepared：
2- indolone derivatives (1a), nitrite tert-butyl (t-BuONO, 2a) and solvent are added into reactor, then Under oxygen atmosphere (1atm), reactor is placed in stirring reaction under room temperature condition, reaction process is monitored through TLC or GC, to anti- The reaction completely of raw material 2- indolone derivatives is answered to stop reaction, it is post-treated to obtain target product (Isatine derivatives, I).
The preparation method for the Isatine derivatives that the present invention is provided, technological process is summarised as (formula four)：
The solvent used can be the mixed of any one or a few in tetrahydrofuran, dioxane, ethyl acetate, toluene Compound, preferably uses any one in tetrahydrofuran or ethyl acetate.
The consumption of the nitrite tert-butyl (t-BuONO, 2a) added be selected from 2- indolone derivatives (1a) consumption 1~ 5 equivalents, preferably 2~3 equivalents.
Described post-processing operation is as follows：By reaction solution saturated common salt water washing, organic phase, aqueous phase acetic acid second are reclaimed Ester is extracted, and merges organic phase；Organic phase is through anhydrous sodium sulfate drying, filtering, vacuum distillation, by residue through column chromatography for separation (petrol ether/ethyl acetate) obtains target product (Isatine derivatives, I).
In the Isatine derivatives that the 2- indolone derivatives and Formulas I that above-mentioned formula 1a is represented are represented, R1Represent what it was connected One or more substituents on phenyl ring, each R1It is independently from each other hydrogen, C1-C6Alkyl, C1-C6Alkoxy, C1-C6Acyl group, C1- C6Ester group, halogen, cyano group, C3-C6Cycloalkyl, C5-C14Aryl, C5-C14Heteroaryl ,-NRaRb.Wherein, Ra, RbIndependently of one another Selected from C1-C6Alkyl or hydrogen；The hetero atom of the heteroaryl is selected from O, S or N.
R2Represent hydrogen, tertbutyloxycarbonyl (Boc), C1-C6Alkyl, C1-C6Acyl group, C3-C6Cycloalkyl, C5-C14Aryl, C5- C14Aryl-C1-C6Alkyl, C5-C14Heteroaryl, the hetero atom of the heteroaryl is selected from O, S or N.Wherein described C5-C14Aryl- C1-C6Alkyl is preferably benzyl.
Wherein, alkyl, alkoxy, cycloalkyl, aryl and heteroaryl can be further substituted with a substituent, and described takes Dai Ji is selected from halogen or C1-C6Alkyl.
Preferably, R1Represent one or more substituents, each R on its phenyl ring connected1Be independently from each other hydrogen, C1-C6Alkyl, halogen；R2Represent hydrogen, tertbutyloxycarbonyl (Boc), phenyl or benzyl.
The beneficial effects of the invention are as follows：A kind of new method for synthesizing Isatine derivatives is proposed, this method uses nitrous acid The tert-butyl ester/O2Catalytic oxidation system, without using metal reagent, react at normal temperatures and pressures, with high yield with purity obtain indigo Red derivative, has the advantages that technological operation is simple and easy to apply, cost is low.
Embodiment
Below in conjunction with specific embodiment, further detailed description is carried out to the present invention.
Embodiment 1-12 reaction condition optimizations
With 2- indolones (1a) for reaction raw materials, isatin (I-1) is prepared with nitrite tert-butyl (2a) reaction, is explored not With influence of the reaction condition for reaction, wherein representative embodiment 1-12 is selected, as a result as shown in Table 1：
Table one：
Embodiment Auxiliary agent (equivalent) Solvent Separate yield
1 TBHP(2) THF 0
2 DTBP(2) THF 0
3 t-BuONO(2) THF 77
4 K2S2O8(2) THF 5
5 t-BuONO(1.2) THF 61
6 t-BuONO(3) THF 76
7a t-BuONO(2) THF 28
8b t-BuONO(2) THF 0
9 t-BuONO(2) Isosorbide-5-Nitrae-dioxane 12
10 t-BuONO(2) EtOAc 75
11 t-BuONO(2) toluene 5
12c t-BuONO(2) THF 70
By taking embodiment 3 as an example, its concrete operations is as follows：Added into schlenk bottles of 10mL 2- indolones (1a, 0.3mmol), nitrite tert-butyl (t-BuONO, 2a, 0.6mmol) and THF (2mL), will then under oxygen atmosphere (1atm) Stirring reaction under the conditions of reactor is placed in 25 DEG C, reaction process is monitored through TLC or GC, complete to reaction raw materials 2- indoles reactive ketones Entirely, stop reaction, by reaction solution saturated common salt water washing, reclaim organic phase, aqueous phase is extracted with ethyl acetate, merge organic Phase；Organic phase is through anhydrous sodium sulfate drying, filtering, vacuum distillation, by residue through column chromatography for separation (petrol ether/ethyl acetate) Obtain target product isatin, I-1,1H NMR (400MHz, DMSO-d6) δ：11.07 (s, 1H), 7.59 (t, J=8.0Hz, 1H), 7.50 (d, J=7.6Hz, 1H), 7.07 (t, J=7.6Hz, 1H), 6.92 (d, J=8.0Hz, 1H)；13C NMR (100MHz, DMSO-d6)δ：184.8,159.8,151.2,138.8,125.1,123.2,118.2,112.7；LRMS (EI, 70eV) m/z (%)：147(M+, 61), 119 (100), 92 (74)
Each embodiment basic operation process of remaining in table one is same as Example 3, wherein：
" a " represents that reaction is carried out under the conditions of air atmosphere (1atm) in embodiment 7；
" b " represents that reaction is carried out under the conditions of nitrogen atmosphere in embodiment 8；
" c " represents that reaction scale is that raw material 2- indolones (1a) inventory used is 1g (7.52mmol) in embodiment 12 Level.
Reaction can not be obtained when others oxidisability auxiliary agent such as TBHP, DTBP is added it can be seen from embodiment 1-12 Obtain target product；Use K2S2O8During as oxidisability auxiliary agent, target product yield is only 5%；Use nitrite tert-butyl (t- BuONO, 2a) as reaction promoter highest yield can be obtained, its optimum initial charge is compound 1a 2 equivalents (embodiment 1- 6).When being carried out under reaction is placed in nitrogen atmosphere, reaction can not occur；Carried out under the conditions of reaction is placed in air atmosphere When, the yield of target product is significantly decreased (embodiment 7-8).It can be obtained and tetrahydrochysene using ethyl acetate as reaction dissolvent Furans target product yield substantially suitable when making solvent, but other reaction dissolvents are then such as toluene, dioxane Reaction does not occur or only obtains very low yield.Inventor has found that reaction scale is that the raw material 2- indolones (1a) used are thrown When doses is 1g (7.52mmol) level, the yield of target product is still up to 70%, illustrates that present invention process is suitable for big rule Mould is produced.
Based on reaction effect under conditions of embodiment 3 preferably, inventor selects the raw material of different substituents on this basis To prepare various Isatine derivatives.
The synthesis of the N-methyl-isatin of embodiment 13
N- methyl -2- indolones (1a, 0.3mmol), nitrite tert-butyl (t- are added into schlenk bottles of 10mL BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirred under the conditions of reactor is placed in into 25 DEG C Reaction, reaction process is monitored through TLC or GC, is stopped reaction, will be reacted to reaction raw materials N- methyl -2- indoles reactive ketone completely Liquid saturated common salt water washing, reclaims organic phase, and aqueous phase is extracted with ethyl acetate, and merges organic phase；Organic phase is through anhydrous slufuric acid Sodium is dried, filtered, vacuum distillation, and residue is obtained into target product N- methyl through column chromatography for separation (petrol ether/ethyl acetate) Isatin, I-2 separates yield 73%,1H NMR (300MHz, CDCl3)δ：7.65-7.58 (m, 2H), 7.14 (t, J=7.5Hz, 1H), 6.91 (d, J=8.1Hz, 1H), 3.26 (s, 3H)；13C NMR (75MHz, CDCl3)δ：183.4,158.3,151.5, 138.5,125.3,123.9,117.5,110.0,26.3；LRMS (EI, 70eV) m/z (%)：161(M+, 82), 133 (40), 104(100).
The synthesis of the N- benzyl isatin of embodiment 14
N- benzyl -2- indolones (1a, 0.3mmol), nitrite tert-butyl (t- are added into schlenk bottles of 10mL BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirred under the conditions of reactor is placed in into 25 DEG C Reaction, reaction process is monitored through TLC or GC, is stopped reaction, will be reacted to reaction raw materials N- benzyl -2- indoles reactive ketone completely Liquid saturated common salt water washing, reclaims organic phase, and aqueous phase is extracted with ethyl acetate, and merges organic phase；Organic phase is through anhydrous slufuric acid Sodium is dried, filtered, vacuum distillation, and residue is obtained into target product N- benzyls through column chromatography for separation (petrol ether/ethyl acetate) Isatin, I-3 separates yield 55%,1H NMR (300MHz, CDCl3)δ：7.58 (d, J=7.2Hz, 1H), 7.47 (t, J= 7.5Hz, 1H), 7.30 (t, J=13.5Hz, 5H), 7.08 (t, J=7.8Hz, 1H), 6.78 (t, J=7.8Hz, 1H), 4.92 (s, 2H)；13C NMR (75MHz, CDCl3)δ：183.3,158.3,150.7,138.4,134.6,129.1,128.2,127.5, 125.4,123.9,117.7,111.1,44.1；LRMS (EI, 70eV) m/z (%)：237(M+, 79), 180 (58), 146 (100).
The synthesis of the N- phenylisatins of embodiment 15
N- phenyl -2- indolones (1a, 0.3mmol), nitrite tert-butyl (t- are added into schlenk bottles of 10mL BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirred under the conditions of reactor is placed in into 25 DEG C Reaction, reaction process is monitored through TLC or GC, is stopped reaction, will be reacted to reaction raw materials N- phenyl -2- indoles reactive ketone completely Liquid saturated common salt water washing, reclaims organic phase, and aqueous phase is extracted with ethyl acetate, and merges organic phase；Organic phase is through anhydrous slufuric acid Sodium is dried, filtered, vacuum distillation, and residue is obtained into target product N- phenyl through column chromatography for separation (petrol ether/ethyl acetate) Isatin, I-4 separates yield 66%,1H NMR (300MHz, CDCl3)δ：7.68 (d, J=7.5Hz, 1H), 7.58-7.52 (m, 3H), 7.48-7.41 (m, 3H), 7.17 (t, J=7.5Hz, 1H), 6.90 (d, J=8.1Hz, 1H)；13C NMR (75MHz, CDCl3)δ：183.0,157.4,151.7,138.5,132.9,130.0,128.9,126.0 (2), 124.4,117.5,111.4； LRMS (EI, 70eV) m/z (%)：223(M+, 18), 195 (100), 167 (42)
The synthesis of the N-Boc isatin of embodiment 16
N-Boc-2- indolones (1a, 0.3mmol), nitrite tert-butyl (t- are added into schlenk bottles of 10mL BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirred under the conditions of reactor is placed in into 25 DEG C Reaction, reaction process is monitored through TLC or GC, stops reaction, by reaction solution to reaction raw materials N-Boc-2- indoles reactive ketone completely Saturated common salt water washing is used, organic phase is reclaimed, aqueous phase is extracted with ethyl acetate, merges organic phase；Organic phase is through anhydrous sodium sulfate Dry, filtering, vacuum distillation, target product N-Boc indigo is obtained by residue through column chromatography for separation (petrol ether/ethyl acetate) Red, I-5 separates yield 57%,1H NMR (300MHz, CDCl3)δ：8.23 (d, J=6.9Hz, 1H), 7.89 (d, J=8.4Hz, 1H), 7.44 (t, J=7.8Hz, 1H), 7.21 (t, J=7.5,1H), 1.67 (s, 9H)；13C NMR (75MHz, CDCl3)δ： 184.1,162.3,148.8,142.9,140.3,132.6,127.9,125.0,115.3,85.1,28.1；LRMS (EI, 70eV) M/z (%)：247(M+, 1), 146 (100), 118 (52)
The synthesis of the 5- chlorisatides of embodiment 17
Added into schlenk bottles of 10mL the chloro- 2- indolones (1a, 0.3mmol) of 5-, nitrite tert-butyl (t-BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirring reaction under the conditions of reactor is placed in into 25 DEG C, Through TLC or GC monitoring reaction process, stop reaction, by reaction solution saturation to the chloro- 2- indoles reactive ketones of reaction raw materials 5- completely Brine It, reclaims organic phase, and aqueous phase is extracted with ethyl acetate, and merges organic phase；Organic phase is through anhydrous sodium sulfate drying, mistake Filter, vacuum distillation, obtain target product 5- chlorisatides, I-6 divides by residue through column chromatography for separation (petrol ether/ethyl acetate) From yield 74%,1H NMR (400MHz, DMSO-d6) δ：11.15 (s, 1H), 7.61 (d, J=8.4Hz, 1H), 7.54 (s, 1H), 6.92 (d, J=8.4Hz, 1H)；13C NMR (100MHz, DMSO-d6) δ：183.8,159.6,149.6,137.7, 127.3,124.6,119.6,114.3；LRMS (EI, 70eV) m/z (%)：183 (M+2,16), 181 (M+, 49), 153 (100), 125(39).
The synthesis of the 5-bromoisatin of embodiment 18
Added into schlenk bottles of 10mL the bromo- 2- indolones (1a, 0.3mmol) of 5-, nitrite tert-butyl (t-BuONO, 2a, 0.6mmol) and THF (2mL), then under oxygen atmosphere (1atm), stirring reaction under the conditions of reactor is placed in into 25 DEG C, Through TLC or GC monitoring reaction process, stop reaction, by reaction solution saturation to the bromo- 2- indoles reactive ketones of reaction raw materials 5- completely Brine It, reclaims organic phase, and aqueous phase is extracted with ethyl acetate, and merges organic phase；Organic phase is through anhydrous sodium sulfate drying, mistake Filter, vacuum distillation, obtain target product 5-bromoisatin, I-6 divides by residue through column chromatography for separation (petrol ether/ethyl acetate) From yield 76%,1H NMR (300MHz, DMSO-d6) δ：11.15 (s, 1H), 7.71 (d, J=8.4Hz, 1H), 7.62 (s, 1H), 6.88 (d, J=8.4Hz, 1H)；13C NMR (75MHz, DMSO-d6) δ：183.7,159.4,150.1,140.5,127.4, 119.9,114.8 (2)；LRMS (EI, 70eV) m/z (%)：227 (M+2,35), 225 (M+, 36), 197 (100), 153 (78)
Applicant states that the present invention illustrates the synthetic method of the present invention, but not office of the invention by above-described embodiment It is limited to above-described embodiment, those skilled in the art it will be clearly understood that what preparation method of the invention and operation were carried out is various It is conventional to replace, select and/or adjust, within the scope of all falling within protection scope of the present invention and being open.

Claims (5)

1. the preparation method of the Isatine derivatives shown in a kind of Formulas I, it is characterised in that 2- Yin shown in formula 1a are added into reactor Nitrite tert-butyl (t-BuONO) and solvent shown in diindyl ketone derivatives, formula 2a, then under oxygen atmosphere, reactor is put In stirring reaction under room temperature condition, reaction process is monitored through TLC or GC, is reacted completely to reaction raw materials 2- indolone derivatives, Stop reaction, the post-treated target product obtained shown in Formulas I；Its reaction equation is：
In the Isatine derivatives that the 2- indolone derivatives and Formulas I that above-mentioned formula 1a is represented are represented, R1Represent on its phenyl ring connected One or more substituents, each R1It is independently from each other hydrogen, C1-C6Alkyl, C1-C6Alkoxy, C1-C6Acyl group, C1-C6Ester Base, halogen, cyano group, C3-C6Cycloalkyl, C5-C14Aryl, C5-C14Heteroaryl ,-NRaRb.Wherein, Ra, RbIt is independently from each other C1-C6Alkyl or hydrogen；The hetero atom of the heteroaryl is selected from O, S or N；
R2Represent hydrogen, tertbutyloxycarbonyl (Boc), C1-C6Alkyl, C1-C6Acyl group, C3-C6Cycloalkyl, C5-C14Aryl, C5-C14Virtue Base-C1-C6Alkyl, C5-C14Heteroaryl, the hetero atom of the heteroaryl is selected from O, S or N, wherein the C5-C14Aryl-C1-C6 Alkyl is preferably benzyl；
Wherein, alkyl, alkoxy, cycloalkyl, aryl and the heteroaryl in described substituent can further be substituted base Substitution, described substituent is selected from halogen or C1-C6Alkyl.
2. preparation method according to claim 1, it is characterised in that described R1Represent on its phenyl ring connected 1 or Multiple substituents, each R1It is independently from each other hydrogen, C1-C6Alkyl, halogen；R2Represent hydrogen, tertbutyloxycarbonyl (Boc), phenyl Or benzyl.
3. preparation method according to claim 1, it is characterised in that described solvents tetrahydrofurane, dioxane, acetic acid Any one or a few mixture in ethyl ester, toluene, preferably uses any one in tetrahydrofuran or ethyl acetate.
4. preparation method according to claim 1, it is characterised in that the use of the nitrite tert-butyl (t-BuONO) added Measure as 1~5 equivalent of 2- indolone derivatives consumptions, preferably 2~3 equivalents.
5. preparation method according to claim 1, it is characterised in that described post-processing operation is as follows：Reaction solution is used full And brine It, organic phase is reclaimed, aqueous phase is extracted with ethyl acetate, merge organic phase；Organic phase through anhydrous sodium sulfate drying, Filtering, vacuum distillation, the target product shown in Formulas I is obtained through column chromatography for separation by residue.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108409630A (en) * 2018-02-07 2018-08-17 宁波大学 The preparation method of 3- hydroxyl -2- indolone derivatives in a kind of water phase
CN108440378A (en) * 2018-03-27 2018-08-24 宁波大学 A kind of preparation method for the 3- amino -2- indolone derivatives that hydrogen peroxide iodo- at room temperature promotes
CN108658836A (en) * 2018-05-15 2018-10-16 宁波大学 A kind of preparation method of 3- substitutions -3- azido indole-2-ketone compounds
CN109734645A (en) * 2019-02-21 2019-05-10 南京金浩医药科技有限公司 A kind of synthesis technology of isatin
CN109810043A (en) * 2018-11-13 2019-05-28 宁波大学 A kind of preparation method of Isatine derivatives

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PARVATHANENI SAI PRATHIMA ET AL.,: ""Synthesis of isatin derivatives under metal free conditions using hypervalent iodine"", 《TETRAHEDRON LETTERS》 *
陈春玉等: ""HBr/t-BuONO催化活化分子氧选择性氧化硫醚"", 《有机化学》 *
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108409630A (en) * 2018-02-07 2018-08-17 宁波大学 The preparation method of 3- hydroxyl -2- indolone derivatives in a kind of water phase
CN108440378A (en) * 2018-03-27 2018-08-24 宁波大学 A kind of preparation method for the 3- amino -2- indolone derivatives that hydrogen peroxide iodo- at room temperature promotes
CN108440378B (en) * 2018-03-27 2021-03-12 宁波大学 Preparation method of iodine-hydrogen peroxide promoted 3-amino-2-indolone derivative at room temperature
CN108658836A (en) * 2018-05-15 2018-10-16 宁波大学 A kind of preparation method of 3- substitutions -3- azido indole-2-ketone compounds
CN108658836B (en) * 2018-05-15 2021-04-20 宁波大学 Preparation method of 3-substituted-3-azidoindole-2-ketone compound
CN109810043A (en) * 2018-11-13 2019-05-28 宁波大学 A kind of preparation method of Isatine derivatives
CN109810043B (en) * 2018-11-13 2021-08-27 宁波大学 Preparation method of isatin derivative
CN109734645A (en) * 2019-02-21 2019-05-10 南京金浩医药科技有限公司 A kind of synthesis technology of isatin

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