CN110483509A - A method of synthesis azepine indoline derivative object - Google Patents
A method of synthesis azepine indoline derivative object Download PDFInfo
- Publication number
- CN110483509A CN110483509A CN201910831394.8A CN201910831394A CN110483509A CN 110483509 A CN110483509 A CN 110483509A CN 201910831394 A CN201910831394 A CN 201910831394A CN 110483509 A CN110483509 A CN 110483509A
- Authority
- CN
- China
- Prior art keywords
- synthesizing
- indoline derivative
- derivative object
- methyl
- rare earth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a kind of methods for synthesizing azepine indoline derivative object, belong to technical field of organic synthesis.The present invention realizes the azaindole quinoline derivant synthesis of structure diversification by rare earth catalyst pyridine carbon-hydrogen bond activation function dough.Specifically under rare-earth catalysis system, the aminopyridine replaced using various alkenyls prepares azaindole quinoline derivant as raw material.The method of the present invention raw material sources are extensive or easily prepared, easy to operate, selective controllable, high income, mild condition, and universality is wide.
Description
Technical field
The present invention relates to technical field of organic synthesis, in particular to pyridine carbon-hydrogen bond activation and intramolecular cyclization reaction to
Realize the azaindole quinoline derivant synthetic method of structure diversification.
Background technique
Azaindole quinoline is a kind of important organic compound, be both natural products and drug important component and
With unique optical property.Therefore, development diversification, efficient azaindole quinoline new synthetic method are always organic synthesis
Important topic in.
Existing to prepare in azaindole quinoline technology, there are the derivative reactions of pyridine skeleton before depending on always to construct nitrogen
Miscellaneous Benzazole compounds skeleton.And classical Fischer indole synthesis and Knut Fridell-Krafft is reacted due to pyridine ring
Short of electricity sub-feature be difficult it is derivative on the synthesis of azaindole quinoline.Document (Org. Lett.2008, 10, 1071-
1074) it reports with suitable (N, N- diallyl amino) bromopyridine for raw material, at -78 DEG C, with super dry pentane-two
Ether (9:1) is solvent, and tert-butyl lithium is as highly basic, the method that azaindole quinoline compound is prepared.The reaction of the type
The disadvantages of that there are functional group compatibilities is poor, severe reaction conditions has certain limitation.Document (Org. Lett. 2015, 17, It 3806-3809) reports and a kind of synthesizes Azaindoles chemical combination using two aminating reaction of high price iodine (III) direct oxidation
The method of object, although this method does not need harsh temperature, but need to carry out halogenation in advance to pyridine, and reaction process disappears
Halogen, complex steps need a large amount of additives, and the poor and most reaction systems of Atom economy are only suitable for constructing product skeleton
More single pyrido cycle compound has certain limitation.
Summary of the invention
The amino that the object of the present invention is to provide a kind of raw material sources extensively, can replace easily to operate from various vinyl
Pyridine is that raw material is highly selective, synthesizes method in azaindole quinoline derivant in high yield.
Above-mentioned technical purpose of the invention has the technical scheme that
A method of synthesis azepine indoline derivative object includes the following steps: the presence in nitrogen protection and rare earth catalyst
Under, in the reaction system for including organic solvent, by heating, the amino replaced with the various vinyl of compound shown in formula (I)
Pyridine is raw material, is inserted into cyclization by carbon-hydrogen bond activation intramolecular, compound azaindole shown in formula (II) is prepared
Quinoline derivant, reaction equation are as follows:
Wherein, R1The independent group in hydrogen, methyl, halogen；R2、R4It is independently selected from hydrogen, the group in methyl；
R3The independent group in methyl, phenyl, benzyl；R5The independent group in hydrogen, methyl, phenyl.
In above-mentioned technical proposal, the rare earth catalyst is selected from Ln [N (SiMe3)2]3, wherein Ln it is independent selected from Sc,
Y, La-Lu or rare earth alkyl complexes.
In above-mentioned technical proposal, the organic solvent is one of toluene, n-hexane or tetrahydrofuran.
It in above-mentioned technical proposal, is calculated with molar ratio, the amount ratio of the formula (I) compound and rare earth catalyst is 1.0:
0.1。
In above-mentioned technical proposal, the temperature of the heating is 100-120 DEG C, the time 24-48 of the heating
h。
It further include dibenzylamine in the reaction system in above-mentioned technical proposal.
In conclusion under rare-earth catalysis system, catalytic pyridine carbon-hydrogen bond activation/function dough and intramolecular insertion cyclisation
Reaction is to realize the synthesis of the azaindole quinoline derivant of structure diversification, and this method Atom economy is high, and bonding is high-efficient,
Reaction condition is mild.Compared to previous methods, reaction condition and substrate universality have clear improvement, this is that other methods are difficult to reality
Existing.The present invention has the following advantages that and innovation:
(1) reaction universality is good, and yield is high, and for most of reaction yield 80% or more, Atom economy is high；
(2) this is rare earth catalyst pyridine carbon-hydrogen bond activation/function dough important supplement, is provided for building nitrogen-containing heterocycle compound
Important thinking；
(3) reaction condition is more mild and does not need a large amount of/cumbersome additives.
(4) this method is also successfully applied to the synthesis of 7-naphthyridine derivatives.
(5) rare earth silicon amido composition catalyst is simple, moderate, commercially available；
The present invention compared with prior art the utility model has the advantages that
Azaindole quinoline derivant quality height, high income are prepared using the method for the present invention；It is good to react universality, reaction of atomic
Economy is high, convenient post-treatment；The building pyrido cyclisation of rare earth metal complex catalytic pyridine carbon-hydrogen bond activation is realized for the first time
Object is closed, the building for azaindole quinoline and other heterocyclic compounds provides important reference.
Detailed description of the invention
Fig. 1 is the reaction equation of present invention synthesis azepine indoline derivative object.
Specific embodiment
Below by specific embodiment, the present invention is described in detail, but the purposes and mesh of this exemplary embodiments
Be only used to enumerate the present invention, any type of any restriction not is constituted to real protection scope of the invention, it is more non-to incite somebody to action this
The protection scope of invention is confined to this.
Embodiment 1
The preparation of 1,3- dimethyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N- picoline -3- amine (0.5 mmol) is added into toluene (3 mL) and urges
Agent Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 1,3- dimethyl -2,3- dihydro -1H- pyrroles at 100 DEG C
[3,2-b] pyridine, product separation yield are 90%.
1H NMR (CDCl3, 500 MHz, ppm): δ 7.75 (d, J = 5.0 Hz, 1H), 6.85 (dd, J
= 5.1, 7.8 Hz, 1H), 6.55 (d, J = 7.9 Hz, 1H), 3.52 (t, J = 8.8 Hz, 1H), 3.26-
3.22 (m, 1H), 2.82 (t, J = 8.5 Hz, 1H), 2.67 (s, 3H), 1.32 (d, J = 7.0 Hz,
3H). 13C NMR (CDCl3, 125 MHz, ppm): δ 156.9, 146.5, 137.8, 121.8, 112.0, 62.1,
36.6, 35.6, 17.1.
Embodiment 2
The preparation of 1,3,5- trimethyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N, 6- lutidines -3- amine (0.5 mmol) is added into toluene (3 mL)
With catalyst Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 1,3,5- trimethyl -2,3- dihydros-at 100 DEG C
1H- pyrroles [3,2-b] pyridine, product separation yield are 81%.
1H NMR (CDCl3, 500 MHz, ppm): δ 6.75 (d, J = 7.9 Hz, 1H), 6.54 (d, J =
7.9 Hz, 1H), 3.47 (t, J = 8.6 Hz, 1H), 3.26-3.21 (m, 1H), 2.84 (t, J = 8.3
Hz, 1H), 2.67 (s, 3H), 2.40 (s, 3H), 1.33 (d, J = 7.0 Hz, 3H). 13C NMR (CDCl3,
125 MHz, ppm): δ 156.6, 146.4, 144.4, 120.8, 113.3, 62.6, 36.9, 36.4, 23.4,
17.5.
Embodiment 3
The preparation of chloro- 1,3- dimethyl -2,3- dihydro -1H- pyrroles [3, the 2-b] pyridine of 5-, structural formula are as follows:
Under nitrogen protection, raw material N- allyl -6- chloro-n-methyl pyridine -3- amine (0.5 is added into toluene (3 mL)
Mmol), dibenzylamine (10 mol%) and catalyst Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 5- at 100 DEG C
Chloro- 1,3- dimethyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, product separation yield are 86%.
1H NMR (CDCl3, 500 MHz, ppm): δ 6.91 (dd, J = 0.6, 8.2 Hz, 1H), 6.55
(d, J = 8.2 Hz, 1H), 3.57 (t, J = 8.9 Hz, 1H), 3.29-3.23 (m, 1H), 2.91 (dd, J
= 8.0, 8.7 Hz, 1H), 2.71 (s, 3H), 1.33 (d, J = 6.9 Hz, 3H). 13C NMR (CDCl3,
125 MHz, ppm):δ 157.4, 145.7, 138.7, 121.7, 114.8, 62.3, 36.6, 35.8, 17.4.
Embodiment 4
The preparation of 1- benzyl -3- methyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N- benzyl pyridine -3- amine (0.5 mmol), two are added into toluene (3 mL)
Benzylamine (10 mol%) and catalyst Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 1- benzyl -3- first at 100 DEG C
Base -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, product separation yield are 83%.
1H NMR (CDCl3, 500 MHz, ppm): δ 7.82 (d, J =4.7 Hz, 1H), 7.36-7.27 (m,
5H), 6.89 (dd, J = 5.2, 7.8 Hz, 1H), 6.62(d, J = 7.8 Hz, 1H), 4.31(d, J =
14.9 Hz, 1H), 4.16(d, J = 14.9 Hz, 1H), 3.60(t, J = 9.0 Hz, 1H), 3.36-3.31
(m, 1H), 2.95(t, J = 8.5 Hz, 1H), 1.38(d, J = 6.9 Hz, 3H). 13C NMR (CDCl3, 125
MHz, ppm): δ 156.9, 145.8, 138.0, 137.6, 128.7, 127.9, 127.5, 121.9, 112.0,
59.8, 53.1, 36.6, 17.6.
Embodiment 5
The preparation of 3- methyl-1-phenyl-2,3- dihydro-1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N- phenylpyridine -3- amine (0.5 mmol), two are added into toluene (3 mL)
Benzylamine (10 mol%) and catalyst Y [N (SiMe3)2]3 (10 mol%), reacts 24 h at 100 DEG C, and product separation yield is
92%。
1H NMR (CDCl3, 500 MHz, ppm): δ 7.91 (d, J = 4.9 Hz, 1H), 7.36 (t, J =
7.6 Hz, 2H), 7.30 (d, J = 8.0 Hz, 1H), 7.19 (d, J = 7.9 Hz, 2H), 7.00 (t, J =
7.3 Hz, 1H), 6.93 (dd, J = 5.0, 8.0 Hz, 1H), 4.11 (t, J = 9.2 Hz, 1H), 3.59
(t, J = 9.0 Hz, 1H), 3.52-3.45 (m, 1H), 1.46 (d, J = 6.9 Hz, 3H),. 13C NMR
(CDCl3, 125 MHz, ppm): δ 157.9, 143.6, 140.6, 139.2, 129.4, 121.7, 121.6,
117.2, 113.4, 58.2, 36.1, 18.1.
Embodiment 6
The preparation of 3- methyl-1-(p-methylphenyl)-2,3- dihydro-1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N- (p-methylphenyl) pyridine -3- amine (0.5 is added into toluene (3 mL)
Mmol), dibenzylamine (10 mol%) and catalyst Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 3- at 100 DEG C
Methyl-1-(p-methylphenyl)-2,3- dihydro-1H- pyrroles [3,2-b] pyridine, product separation yield are 61%.
1H NMR (CDCl3, 500 MHz, ppm): δ 7.88 (d, J = 4.8 Hz, 1H), 7.23 (d, J =
8.0 Hz, 1H), 7.17 (d, J = 8.3 Hz, 2H), 7.10 (d, J = 8.4 Hz, 2H), 6.93 (dd, J
= 5.1, 7.8 Hz, 1H), 4.09 (t, J = 9.0 Hz, 1H), 3.57 (t, J = 8.7 Hz, 1H), 3.52-
3.46 (m, 1H), 2.33 (s, 3H), 1.46 (d, J = 6.8 Hz, 3H),. 13C NMR (CDCl3, 125
MHz, ppm): δ 157.7, 141.2, 141.1, 138.6, 131.5, 130.0, 121.7, 117.7, 113.2,
58.5, 36.2, 20.8, 18.1.
Embodiment 7
The preparation of 1- (4- chlorphenyl) -3- methyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, structural formula are as follows:
Under nitrogen protection, raw material N- allyl-N- (4- chlorphenyl) pyridine -3- amine (0.5 is added into toluene (3 mL)
Mmol), dibenzylamine (10 mol%) and catalyst Y [N (SiMe3)2]3 (10 mol%) reacts 24 h preparation 1- at 100 DEG C
(4- chlorphenyl) -3- methyl -2,3- dihydro -1H- pyrroles [3,2-b] pyridine, product separation yield are 87%.
1H NMR (CDCl3, 500 MHz, ppm): δ 7.91 (d, J = 4.9 Hz, 1H), 7.30-7.27
(m, 2H), 7.24 (d, J = 8.1 Hz, 1H), 7.12-7.08 (m, 2H), 6.94 (dd, J = 5.0, 8.0
Hz, 1H), 4.08 (t, J = 8.8 Hz, 1H), 3.57-3.46 (m, 2H), 1.45 (d, J = 6.7 Hz,
3H). 13C NMR (CDCl3, 125 MHz, ppm): δ 157.8, 142.1, 140.3, 139.5, 129.4,
126.4, 121.7, 118.4, 113.6, 58.3, 36.1, 18.1.
It should be noted that the organic solvent toluene in embodiment 1-6 could alternatively be n-hexane or tetrahydrofuran, reaction temperature
It can be changed according to the actual situation in 100-120 DEG C and 24-48 h of section respectively with the reaction time.
Finally, it should be noted that the above embodiments are only used to illustrate the technical solution of the present invention., rather than its limitations；To the greatest extent
Pipe present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that: its according to
Right scientific research modifies the technical solutions described in the foregoing embodiments, or to some or all of the technical features into
Row equivalent replacement；And these are modified or replaceed, various embodiments of the present invention technology that it does not separate the essence of the corresponding technical solution
The range of scheme.
Claims (6)
1. a kind of method for synthesizing azepine indoline derivative object, which comprises the steps of: in nitrogen protection and rare earth
In the presence of catalyst, in the reaction system for including organic solvent, by heating, with the various ethylene of compound shown in formula (I)
The aminopyridine that base replaces is raw material, is inserted into cyclization by carbon-hydrogen bond activation intramolecular, formula (II) shownization is prepared
Close object azaindole quinoline derivant, reaction equation are as follows:
Wherein, R1The independent group in hydrogen, methyl, halogen；R2、R4It is independently selected from hydrogen, the group in methyl；R3
The independent group in methyl, phenyl, benzyl；R5The independent group in hydrogen, methyl, phenyl.
2. a kind of method for synthesizing azepine indoline derivative object according to claim 1, it is characterised in that: the rare earth
Catalyst is selected from Ln [N (SiMe3)2]3, wherein Ln is independent is selected from Sc, Y, La-Lu or rare earth alkyl complexes.
3. a kind of method for synthesizing azepine indoline derivative object according to claim 1, it is characterised in that: described is organic
Solvent is one of toluene, n-hexane or tetrahydrofuran.
4. a kind of method for synthesizing azepine indoline derivative object according to claim 1, it is characterised in that: with molar ratio computing
It calculates, the amount ratio of the formula (I) compound and rare earth catalyst is 1.0:0.1.
5. a kind of method for synthesizing azepine indoline derivative object according to claim 1, it is characterised in that: the heating
Temperature be 100-120 DEG C, 24-48 h of time of the heating.
6. a kind of method for synthesizing azepine indoline derivative object according to claim 1, it is characterised in that: the reaction
It further include dibenzylamine in system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910831394.8A CN110483509B (en) | 2019-09-04 | 2019-09-04 | Method for synthesizing nitrogenous heterocyclic derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910831394.8A CN110483509B (en) | 2019-09-04 | 2019-09-04 | Method for synthesizing nitrogenous heterocyclic derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110483509A true CN110483509A (en) | 2019-11-22 |
| CN110483509B CN110483509B (en) | 2020-08-25 |
Family
ID=68556297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910831394.8A Active CN110483509B (en) | 2019-09-04 | 2019-09-04 | Method for synthesizing nitrogenous heterocyclic derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110483509B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773244A (en) * | 2021-04-06 | 2021-12-10 | 复旦大学 | Method for removing ketone fragment in nitrogen heterocyclic compound substituent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1678581A (en) * | 2002-07-03 | 2005-10-05 | 拜耳医药保健股份公司 | Indolin phenylsulfonamide derivatives |
| CN104870441A (en) * | 2012-10-19 | 2015-08-26 | 阿斯特克斯治疗有限公司 | Bicyclic heterocycle compounds and their uses in therapy |
| WO2019020792A1 (en) * | 2017-07-27 | 2019-01-31 | Esteve Pharmaceuticals, S.A. | New propanamine derivatives for treating pain and pain related conditions |
-
2019
- 2019-09-04 CN CN201910831394.8A patent/CN110483509B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1678581A (en) * | 2002-07-03 | 2005-10-05 | 拜耳医药保健股份公司 | Indolin phenylsulfonamide derivatives |
| CN104870441A (en) * | 2012-10-19 | 2015-08-26 | 阿斯特克斯治疗有限公司 | Bicyclic heterocycle compounds and their uses in therapy |
| WO2019020792A1 (en) * | 2017-07-27 | 2019-01-31 | Esteve Pharmaceuticals, S.A. | New propanamine derivatives for treating pain and pain related conditions |
Non-Patent Citations (2)
| Title |
|---|
| GUOYONG SONG ET AL.: "Enantioselective C-H Bond Addition of Pyridines to Alkenes Catalyzed by Chiral Half-Sandwich Rare-Earth Complexes", 《J. AM. CHEM. SOC.》 * |
| SAMUELE BORDI AND JEREMY T. STARR: "Hydropyridylation of Olefins by Intramolecular Minisci Reaction", 《ORG. LETT.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773244A (en) * | 2021-04-06 | 2021-12-10 | 复旦大学 | Method for removing ketone fragment in nitrogen heterocyclic compound substituent |
| CN113773244B (en) * | 2021-04-06 | 2024-03-22 | 复旦大学 | Method for removing ketone fragment in nitrogen heterocyclic compound substituent |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110483509B (en) | 2020-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Blay et al. | Recent developments in asymmetric alkynylation of imines | |
| Berk et al. | Development of a titanocene-catalyzed enyne cyclization/isocyanide insertion reaction | |
| Stolley et al. | Nickel‐Catalyzed [2+ 2+ 2] Cycloaddition of Diynes and Cyanamides | |
| MY131740A (en) | Method of polymerization | |
| DE60316728D1 (en) | PHOSPHONIUM AND IMIDAZOLIUM SALTS AND PROCESS FOR THE PRODUCTION THEREOF | |
| Overman et al. | Iminium ion and acyl iminium ion initiated cyclizations of vinylsilanes. Regiocontrolled construction of unsaturated azacyclics | |
| KR102586087B1 (en) | Processes for the preparation of a diarylthiohydantoin compound | |
| Bai et al. | Quinine-catalyzed asymmetric domino Mannich-cyclization reactions of 3-isothiocyanato oxindoles with imines for the synthesis of spirocyclic oxindoles | |
| Fan et al. | AN-Phosphinoamidinato NHC-Diborene Catalyst for Hydroboration | |
| AU2001271145A1 (en) | Catalyst for asymmetric (transfer) hydrogenation | |
| Huang et al. | Cycloamidination of Aminoalkenes with Nitriles: Synthesis of Substituted 2‐Imidazolines and Tetrahydropyrimidines | |
| Ravinder et al. | Amide activation by TMSCl: reduction of amides to amines by LiAlH4 under mild conditions | |
| Ghorai et al. | Cp* Co (iii)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds | |
| BR112012024682B1 (en) | processes to contact, to manufacture and to form a compound as well as a compound | |
| Tabor et al. | Synthesis of Lepadiformine Using a Hydroamination Transform | |
| CN110483509A (en) | A method of synthesis azepine indoline derivative object | |
| Coussanes et al. | Radical cyclization of trichloroacetamides: synthesis of lactams | |
| CN109293706A (en) | The trivalent iridium imine composition of the dual key of nitrogen containing iridium, preparation method and applications | |
| Kanyiva et al. | Practical approach for hydroheteroarylation of alkynes using bench-stable catalyst | |
| Zhang et al. | Intramolecular C (sp³)–H Bond Amination Strategies for the Synthesis of Saturated N-containing Heterocycles | |
| EP3429999A1 (en) | Method for preparing alkylamines | |
| AU2008300526A1 (en) | Accelerated reduction of organic substances with boranes | |
| FR2825707B1 (en) | PROCESS FOR THE PREPARATION OF CARBEN-BASED METAL CATALYSTS FOR THE HYDROSILYLATION OF UNSATURATED COMPOUNDS AND CATALYSTS OF THIS TYPE | |
| Huehls et al. | Diastereoselective synthesis of pyrroloindolines using α, β-unsaturated N-aryl ketonitrones and activated alkynes | |
| CN108997194A (en) | A kind of synthetic method of amino isoindole derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |