CN106432000A - Method for synthesizing sulfoximine compounds from thioether - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/06—Sulfinamides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Abstract
The invention discloses a synthetic method for synthesizing sulfoximine compounds from thioether in one step and application thereof. The synthetic method disclosed by the invention comprises the step of mixing the thioether, an ammonia source and an organic solvent together for carrying out an oxidizing reaction in the presence of an oxidizing agent, thereby obtaining the corresponding sulfoximine compounds. According to the invention, one-step synthesis of the sulfoximine compounds from the thioether is realized for the first time. In recent years, the sulfoximine structure is introduced into the existing drug molecules or high-activity compound molecules, and many high-activity molecules at the clinical stage and listed drug molecules appear. According to the method disclosed by the invention, the drug molecules containing the sulfoximine structure are produced, and the industrial cost can be greatly reduced; and moreover, the synthetic method provided by the invention has the advantages of being high in yield, readily available in raw materials, simple in conditions, simple in reaction equipment, easy in industrialized production, and the like. The structural formula is as shown in the specification.
Description
Technical field
The present invention relates to a kind of synthetic method for being synthesized sulfenimide class compound by thioether single step reaction, belongs to thioether
Oxidation reaction.
Background technology
Sulfenimide and its derivant are that a class has biological activity, are widely present in pesticide and medicine etc. biological living
Molecule fragment in property molecule.Sulfenimide as the isostere of sulfone, nitrogen-atoms provide can decorating site, also become
The emphasis of drug development concern.Meanwhile, sulfenimide can also be used as chiral auxiliary, and the part of asymmetry catalysis is hydrocarbon
The homing device of activation.In recent years, by existing for the introducing of sulfenimide structure drug molecule or high-activity compound are divided
Son, occur in that a lot of high activity molecules and listed drug molecule (Angew.Chem.Int.Ed.2013,52,9399-
9408), it is shown below：
In recent years, sulfenimide is of increased attention, and it is interested that its synthetic method is always people
Work.Existing lot of documents reports the synthetic method of sulfenimide, for example：Sulfoxide and Hydrazoic acid,sodium salt strong sulfuric acid response system
Standby sulfenimide class compound (H.R.Bentley, E.E.McDermott, J.K.Whitehead,
Proc.R.Soc.London Ser.B 1951,138,265.)；Sulfoxide prepares sulfenimide class with MSH or DPH reaction
Compound ((a) J.Mendiola, J.A.Rincon, C.Mateos, J.F.Soriano, O.de Frutos, J.K.Niemeier,
E.M.Davis, Org.Process Res.Dev.2009,13,263-267；(b) Y.Tamura, J.Minamikawa,
K.Sumoto, S.Fujii, M.Ikeda, J.Org.Chem.1973,38,1239-1241.)；Sulfoxide and sulfanilamide, trifluoroacetyl
Amine, carbamate etc., react under conditions of metallic catalyst, then deprotection generates sulfenimide class compound ((a)
H.Okamura, C.Bolm, Org.Lett.2004,6,1305-1307；(b) O.G.Manche, C.Bolm,
Org.Lett.2006,8,2349-2352；(c) M.Zenzola, R.Doran, R.Luisi, J.A.Bull,
J.Org.Chem.2015,80,6391-6399；(d) V.Bizet, L.Buglioni, C.Bolm,
Angew.Chem.Int.Ed.2014,53,5639-5642.).But these methods have significant limitation, such as：Using danger
Hydrazoic acid,sodium salt and concentrated sulphuric acid, need synthesize activating reagent MSH or DPH, need using metallic catalyst and need deprotection, and
And be required for by thioether initial oxidation being sulfoxide, then react with reaction reagent.
2016, Renzo Luisi and James A.Bull report sulfoxide in the presence of iodobenzene diacetate with amino
Ammonium formate reaction prepares sulfenimide class compound (Angew.Chem.Int.Ed.2016,55,7203-7207), the method
Do not need metal catalytic and part, it is not necessary in advance by ammonia source protection, can be by sulfoxide and carbamic acid amine single step reaction
Obtain sulfenimide product.And the method has raw material and is easy to get, yield height, the advantages of the response time is short.And the present invention exists
New breakthrough is achieved on the basis of which, in contrast, with advantages below：Sulfenimide is obtained by thioether single step reaction
Class compound, it is not necessary to prepare sulfoxide in advance；Ammonia source is more extensive with respect to which, and the present invention can use ammonia as ammonia source, and
Used in document, ammonia does not react, and much cheap ammonia source, such as ammonium nitrate, ammonium fluoride, ammonium carbonate etc. all can be used as these
The ammonia source of invention, therefore the present invention be more suitable for commercial production；The present invention is more efficient with respect to which, and the yield of a lot of substrates all may be used
Reach more than 90%, and the response time is shorter etc..
Content of the invention
Technical problem solved by the invention is to provide a kind of simple method by thioether one-step synthesis sulfenimide.
The method need not use metal catalytic, and raw material is simple and easy to get, and condition is simple, and universality is good.
The purpose of the present invention is realized by below scheme：
The reaction expression of sulfenimide class compound is for shown in I：
Under oxidant effect, ammonia source, thioether and organic solvent are mixed carries out oxidation reaction, uses thin layer chromatography
TLC tracks reaction process.Reaction is finished, and solvent under reduced pressure is removed, and crude product is through 200-300 mesh silica gel column chromatography purification.Each original
The consumption of material is：The molar ratio of thioether, ammonia source and oxidant is 1: 1-50: 1-50.The temperature of described sulfide oxidation reaction
For -100-200, preferably 30 degree, the response time is 0.5h-12h.
Wherein R1Selected from C1-20Alkyl and corresponding derivant, aromatic radical and replace aromatic radical, thiazolinyl and replace
Thiazolinyl, alkynyl and the alkynyl etc. for replacing.Described R1In, C1-20Alkyl and corresponding derivant include methyl, ethyl, different
Propyl group, cyclopropyl, aldehyde radical replace alkyl, cyano group to replace alkyl, alkenyl substituted alkyl, alkynyl substituted alkyl, aromatic rings to replace alkane
Base, the halogen-substituted alkyl such as fluorine-containing, replace containing carboxylic acid and its derivant alkyl, replace alkyl containing nitro, containing amino and its derivative
Thing replaces alkyl, hydroxyl and its derivant to replace alkyl etc..R1Middle aromatic radical and the aromatic radical for replacing, including phenyl and replacement
Phenyl, naphthyl and substituted naphthyl, furyl and substituted furan base, thienyl and substituted thiophene base, thiazolyl and substituted thiazolyl,
Pyridine radicals and substituted pyridinyl, pyrimidine and substituted pyrimidyl, pyrrole radicals and substituted azole base, imidazole radicals and substituted imidazole base, Yin
Diindyl base and substituted indolyl, quinolyl and substd quinolines base and some benzheterocycle substituent groups etc..R1Middle thiazolinyl and replacement
Thiazolinyl, including vinyl, acrylic, styryl, aldehyde radical substituted alkenyl, cyano group substituted alkenyl, alkynyl substituted thiazolinyl, aromatic rings
Substituted alkenyl, the halogen substiuted thiazolinyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkenyl, substituted alkenyl containing nitro, contain amino and
Its derivant substituted alkenyl, hydroxyl and its derivant substituted alkenyl etc..R1Middle alkynyl and replace alkynyl, including acetenyl,
Propinyl, phenylacetylene base, aldehyde radical substituted alkynyl, cyano group substituted alkynyl, alkenyl substituted alkynyl, aromatic rings substituted alkynyl, fluorine-containing etc.
Halogen substiuted alkynyl, containing carboxylic acid and its derivant substituted alkynyl, substituted alkynyl containing nitro, containing amino and its derivant replacement alkynes
Base, hydroxyl and its derivant substituted alkynyl etc..
Wherein R2Selected from C1-20Alkyl and corresponding derivant, aromatic radical and replace aromatic radical, thiazolinyl and replace
Thiazolinyl, alkynyl and the alkynyl etc. for replacing.Described R2In, C1-20Alkyl and corresponding derivant include methyl, ethyl, different
Propyl group, cyclopropyl, aldehyde radical replace alkyl, cyano group to replace alkyl, alkenyl substituted alkyl, alkynyl substituted alkyl, aromatic rings to replace alkane
Base, the halogen-substituted alkyl such as fluorine-containing, replace containing carboxylic acid and its derivant alkyl, replace alkyl containing nitro, containing amino and its derivative
Thing replaces alkyl, hydroxyl and its derivant to replace alkyl etc..R2Middle aromatic radical and the aromatic radical for replacing, including phenyl and replacement
Phenyl, naphthyl and substituted naphthyl, furyl and substituted furan base, thienyl and substituted thiophene base, thiazolyl and substituted thiazolyl,
Pyridine radicals and substituted pyridinyl, pyrimidine and substituted pyrimidyl, pyrrole radicals and substituted azole, imidazole radicals and substituted imidazole base, indole
Base and substituted indolyl, quinolyl and substd quinolines base and some benzheterocycle substituent groups etc..R2Middle thiazolinyl and the alkene for replacing
Base, takes including vinyl, acrylic, styryl, aldehyde radical substituted alkenyl, cyano group substituted alkenyl, alkynyl substituted thiazolinyl, aromatic rings
For thiazolinyl, the halogen substiuted thiazolinyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkenyl, substituted alkenyl containing nitro, contain amino and its
Derivant substituted alkenyl, hydroxyl and its derivant substituted alkenyl etc..R2Middle alkynyl and replace alkynyl, including acetenyl, third
Alkynyl, phenylacetylene base, aldehyde radical substituted alkynyl, cyano group substituted alkynyl, alkenyl substituted alkynyl, aromatic rings substituted alkynyl, the halogen such as fluorine-containing
Plain substituted alkynyl, containing carboxylic acid and its derivant substituted alkynyl, substituted alkynyl containing nitro, contain amino and its derivant substituted alkynyl,
Hydroxyl and its derivant substituted alkynyl etc..
In above-mentioned synthetic method, described oxidant includes iodine, bromine, N- chlorosuccinimide, N- bromo succinyl
Imines, N- N-iodosuccinimide, iodosobenzene, 2- iodosobenzoic acid (IBX), Dess-Martin oxidant (DMP), iodine
Phenylenediacetic Acid and its derivant etc..
In above-mentioned synthetic method, described ammonia source includes ammonium chloride, ammonium nitrate, ammonium fluoride, ammonium carbonate, ammonium hydrogen carbonate, ammonia
Base ammonium formate, ammonium formate, ammonium acetate, ammonia, ammonia, the organic solvent of ammonia, benzoic acid ammonia etc..
In above-mentioned synthetic method, described solvent includes toluene, acetonitrile, ether, dichloromethane, 1,2- dichloroethanes, first
Alcohol, ethanol, isopropanol, nitromethane, acetone, dimethyl sulfoxide, DMF or ethyl acetate etc..
Specific embodiment
Further described using following embodiments, but these embodiments are only exemplary, are not intended to limit the present invention's
Scope.It will be understood by those skilled in the art that to technical solution of the present invention under without departing from the spirit and scope of the present invention
Details and the modification that carries out of form or replacement, will fall within the scope of protection of the present invention.
Embodiment 1
By thioether(124mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate (308mg,
4.0mol) add in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent is removed after the completion of reaction, at column chromatography
Reason, prepared product139mg, yield 90%.
Embodiment 2
By thioether(169mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product190mg, yield 95%.
Embodiment 3
By thioether(169mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate (308mg,
4.0mol) add in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent is removed after the completion of reaction, at column chromatography
Reason, prepared product186mg, yield 93%.
Embodiment 4
By thioether(138mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product135mg, yield 80%.
Embodiment 5
By thioether(138mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product155mg, yield 92%.
Embodiment 6
By thioether(203mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product208mg, yield 89%.
Embodiment 7
By thioether(142mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product163mg, yield 94%.
Embodiment 8
By thioether(154mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product163mg, yield 88%.
Embodiment 9
By thioether(166mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product134mg, yield 70%.
Embodiment 10
By thioether(186mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product202mg, yield 93%.
Embodiment 11
By thioether(228mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product220mg, yield 85%.
Embodiment 12
By thioether(279mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), acetic acid
Ammonium (308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent is removed after the completion of reaction,
Column chromatography is processed, prepared product279mg, yield 90%.
Embodiment 13
By thioether(194mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product196mg, yield 87%.
Embodiment 14
By thioether(228mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product210mg, yield 81%.
Embodiment 15
By thioether(174mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product185mg, yield 90%.
Embodiment 16
By thioether(200mg, 1.0mol), iodobenzene diacetate (966mg, 3.0mol), ammonium acetate
(308mg, 4.0mol) is added in the reaction bulb containing ethanol 10ml, room temperature reaction two hours.Solvent, post is removed after the completion of reaction
Image processing, prepared product176mg, yield 76%.
Claims (6)
1. the reaction expression of sulfenimide class compound is synthesized by thioether for shown in I：
Wherein R1Selected from C1-20Alkyl and corresponding derivant, aromatic radical and replace aromatic radical, thiazolinyl and replace alkene
Base, alkynyl and the alkynyl etc. for replacing.
Wherein R2Selected from C1-20Alkyl and corresponding derivant, aromatic radical and replace aromatic radical, thiazolinyl and replace alkene
Base, alkynyl and the alkynyl etc. for replacing.
Generate sulfenimide class compound synthetic method be：Under oxidant effect, ammonia source, thioether and organic solvent are mixed
Being combined carries out oxidation reaction and obtains final product.The consumption of each raw material is：The molar ratio of thioether, ammonia source and oxidant is 1: 1-50:
1-50.The temperature of described sulfide oxidation reaction is -100-200 degree Celsius.Response time is 0.5h-12h.
2. a kind of synthesis claim 1 described in R1In, C1-20Alkyl and corresponding derivant include methyl, ethyl, isopropyl
Base, cyclopropyl, aldehyde radical alkane substitute, cyano group alkane substitute, alkenyl substituted alkane, alkynyl substituted alkane, aromatic rings alkane substitute,
Fluorine-containing wait halogen substiuted alkane, containing carboxylic acid and its derivant alkane substitute, containing nitro substituted alkanes, take containing amino and its derivant
For alkane, hydroxyl and its derivant alkane substitute etc..
R1Middle aromatic radical and the aromatic radical for replacing, including phenyl and substituted-phenyl, naphthyl and substituted naphthyl, furyl and replacement furan
Mutter base, thienyl and substituted thiophene base, thiazolyl and substituted thiazolyl, pyridine radicals and substituted pyridinyl, pyrimidine and substituted pyrimidines
Base, pyrrole radicals and substituted azole, imidazole radicals and substituted imidazole base, indyl and substituted indolyl, quinolyl and substd quinolines base
And some benzheterocycle substituent groups etc..
R1Middle thiazolinyl and replace thiazolinyl, including vinyl, acrylic, styryl, aldehyde radical substituted alkenyl, cyano group substituted alkenyl,
Alkynyl substituted thiazolinyl, aromatic rings substituted alkenyl, the halogen substiuted thiazolinyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkenyl, contain nitre
Base substituted alkenyl, containing amino and its derivant substituted alkenyl, hydroxyl and its derivant substituted alkenyl etc..
R1Middle alkynyl and replace alkynyl, including acetenyl, propinyl, phenylacetylene base, aldehyde radical substituted alkynyl, cyano group substituted alkynyl,
Alkenyl substituted alkynyl, aromatic rings substituted alkynyl, the halogen substiuted alkynyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkynyl, contain nitre
Base substituted alkynyl, containing amino and its derivant substituted alkynyl, hydroxyl and its derivant substituted alkynyl etc..
3. a kind of synthesis claim 1 described in R2In, C1-20Alkyl and corresponding derivant include methyl, ethyl, isopropyl
Base, cyclopropyl, aldehyde radical alkane substitute, cyano group alkane substitute, alkenyl substituted alkane, alkynyl substituted alkane, aromatic rings alkane substitute,
Fluorine-containing wait halogen substiuted alkane, containing carboxylic acid and its derivant alkane substitute, containing nitro substituted alkanes, take containing amino and its derivant
For alkane, hydroxyl and its derivant alkane substitute etc..
R2Middle aromatic radical and the aromatic radical for replacing, including phenyl and substituted-phenyl, naphthyl and substituted naphthyl, furyl and replacement furan
Mutter base, thienyl and substituted thiophene base, thiazolyl and substituted thiazolyl, pyridine radicals and substituted pyridinyl, pyrimidine and substituted pyrimidines
Base, pyrrole radicals and substituted azole, imidazole radicals and substituted imidazole base, indyl and substituted indolyl, quinolyl and substd quinolines base
And some benzheterocycle substituent groups etc..
R2Middle thiazolinyl and replace thiazolinyl, including vinyl, acrylic, styryl, aldehyde radical substituted alkenyl, cyano group substituted alkenyl,
Alkynyl substituted thiazolinyl, aromatic rings substituted alkenyl, the halogen substiuted thiazolinyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkenyl, contain nitre
Base substituted alkenyl, containing amino and its derivant substituted alkenyl, hydroxyl and its derivant substituted alkenyl etc..
R2Middle alkynyl and replace alkynyl, including acetenyl, propinyl, phenylacetylene base, aldehyde radical substituted alkynyl, cyano group substituted alkynyl,
Alkenyl substituted alkynyl, aromatic rings substituted alkynyl, the halogen substiuted alkynyl such as fluorine-containing, containing carboxylic acid and its derivant substituted alkynyl, contain nitre
Base substituted alkynyl, containing amino and its derivant substituted alkynyl, hydroxyl and its derivant substituted alkynyl etc..
4. in accordance with the method for claim 2, it is characterised in that：Described oxidant includes iodine, bromine, N- chloro succinyl
Imines, N- bromo-succinimide, N- N-iodosuccinimide, iodosobenzene, 2- iodosobenzoic acid (IBX), Dess-
Martin oxidant (DMP), iodobenzene diacetate and its derivant, hydrogen peroxide etc..Can using therein one or more.
5. in accordance with the method for claim 2, it is characterised in that：Described ammonia source include ammonium chloride, ammonium nitrate, ammonium fluoride,
Ammonium carbonate, ammonium hydrogen carbonate, carbamic acid amine, ammonium formate, ammonium acetate, ammonia, ammonia, the organic solvent of ammonia, benzoic acid ammonia etc..Can
With using therein one or more.
6. in accordance with the method for claim 2, it is characterised in that：Described solvent includes toluene, acetonitrile, ether, dichloromethane
Alkane, 1,2- dichloroethanes, methanol, ethanol, isopropanol, nitromethane, acetone, dimethyl sulfoxide, DMF or second
Acetoacetic ester etc..Can using therein one or more.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113402434A (en) * | 2021-06-17 | 2021-09-17 | 常州工程职业技术学院 | Novel NH-sulfoxide imine compound and synthetic method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305468A (en) * | 1998-05-08 | 2001-07-25 | 弗莱克斯塞思美国有限合伙公司 | Process for the preparation of sulfenimides |
| US20080108666A1 (en) * | 2006-11-08 | 2008-05-08 | Loso Michael R | Heteroaryl (substituted)alkyl N-substituted sulfoximines as insecticides |
-
2016
- 2016-09-21 CN CN201610843028.0A patent/CN106432000A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1305468A (en) * | 1998-05-08 | 2001-07-25 | 弗莱克斯塞思美国有限合伙公司 | Process for the preparation of sulfenimides |
| US20080108666A1 (en) * | 2006-11-08 | 2008-05-08 | Loso Michael R | Heteroaryl (substituted)alkyl N-substituted sulfoximines as insecticides |
Non-Patent Citations (1)
| Title |
|---|
| MARINA ZENZOLA等: ""Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides"", 《ANGEW. CHEM. INT. ED.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113402434A (en) * | 2021-06-17 | 2021-09-17 | 常州工程职业技术学院 | Novel NH-sulfoxide imine compound and synthetic method thereof |
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