CN109020844A - A kind of method that benzene sulfonyl hydrazide analog derivative synthesizes benzenesulfonamides without metal catalytic with secondary amine - Google Patents
A kind of method that benzene sulfonyl hydrazide analog derivative synthesizes benzenesulfonamides without metal catalytic with secondary amine Download PDFInfo
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- CN109020844A CN109020844A CN201811240921.XA CN201811240921A CN109020844A CN 109020844 A CN109020844 A CN 109020844A CN 201811240921 A CN201811240921 A CN 201811240921A CN 109020844 A CN109020844 A CN 109020844A
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- secondary amine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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Abstract
A kind of method that benzene sulfonyl hydrazide analog derivative synthesizes benzenesulfonamides without metal catalytic with secondary amine, it is under air environment, using benzene sulfonyl hydrazide analog derivative and secondary amine as substrate, containing iodine compound as catalyst, tert-butyl hydroperoxide is oxidant, in a solvent in 80-120 DEG C of generation S-N key coupling reaction, benzenesulfonamides are generated.Catalyst used in this method is simple and easy to get, stable in the air, and recycling is simple and pollution-free, and the present invention has broad application prospects in pharmaceutical synthesis and industrial production.
Description
Technical field
The invention belongs to organic syntheses, pharmaceutical synthesis field, are related to the synthetic method of benzenesulfonamides, specifically relate to
And under the conditions of one kind is nonmetal catalyzed, the catalysis benzene sulfonyl hydrazide analog derivative containing iodine compound synthesizes benzene sulfonamide with secondary amine
The method for closing object.
Background technique
Benzenesulfonamides are often obtained by the aminating reaction of benzene sulfonyl chloride.This substance have it is potent it is antimycotic,
Bacterium, anticancer, antipsychotics, the bioactivity such as anti-HIV protease inhibitors.Major part is utilized as effective half Guang
Serine protease and carbonic acid protease inhibitors.Therefore, the synthetic method for developing benzenesulfonamides has important reality
With value.
Currently, synthetic method of the benzenesulfonamides under transition metal-catalyzed there are many, such as: Ke Yi
FeCl2Catalyst system in, S-N key is constructed by the direct coupling of aryl sulfonic acid sodium and nitro-aromatic and is catalyzed and synthesized come single step
Sulfonamide；Pass through CuBr2Catalysis sulfonic acid chloride is reacted with tertiary amine generate sulfonamide etc..But above-mentioned present synthesis benzene sulphur
Amide substance needs transition metal-catalyzed (including some toxic metals), and toxic metals can generate pollution, atom warp to environment
Ji property is general, and most of reaction raw materials are expensive and are not easy to obtain.This is but also they receive certain limit in the industrial production
System.
S-N key coupling nonmetal catalyzed in recent years makes great progress.2016, Lai J et al. the study found that
By be added the catalysis of suitable elemental iodine benzene sulfonyl chloride and tertiary amine S-N coupling reaction can under mild conditions into
Row, so the coupling of the S-N key of nonmetal catalyzed benzene sulfonyl chloride and tertiary amine is generated.Currently, there are no utilize to contain both at home and abroad
Iodine compound is catalyzed S-N key under air environment and is coupled the open source literature to form benzenesulfonamides and patent application.
Summary of the invention
It is an object of the present invention in view of the above shortcomings of the prior art, a kind of benzene sulfonyl hydrazide analog derivative and two are provided
Method of the grade amine without metal catalytic synthesis benzenesulfonamides, this method are simply made containing iodine compound with cheap and easily-available
For catalyst, under air environment, so that it may so that the life of benzene sulfonyl hydrazide analog derivative high yield under conditions of temperature is 120 DEG C
At required benzenesulfonamides.
To achieve the above object, the technical solution adopted by the present invention are as follows: a kind of benzene sulfonyl hydrazide analog derivative and secondary amine without
The method that metal catalytic synthesizes benzenesulfonamides, this method be under air environment, with benzene sulfonyl hydrazide analog derivative and
Secondary amine is substrate, and containing iodine compound as catalyst, tert-butyl hydroperoxide is oxidant, and it is even that S-N key occurs in a solvent
Connection reaction, generates benzenesulfonamides；Wherein, the general formula of benzene sulfonyl hydrazide analog derivative isR1For
Hydrogen, halogen or substituent group.
If being write secondary amine as general formulaThen reaction formula is as follows:
Preferably, R1For H, halogen, methyl, cyano or methoxyl group；Secondary amine is nafoxidine, morpholine, dibenzylamine, N- second
Base aniline, piperidines or N methyl pmpyl amine.
The above-mentioned iodine compound that contains is KI, NH4I or tetrabutylammonium iodide, preferably NH4I；Solvent is THF, toluene, CH3CN
Or DMF, preferably THF；Reaction temperature be 80-120 DEG C, preferably 120 DEG C, time 6-15h, preferably 10h.When reaction starts, benzene
Sulfonyl hydrazines derivative, secondary amine, the molar ratio of catalyst and oxidant are 1:2:0.1:0.5.
The present invention carries out S-N key with secondary amine in the environment of air, with the simply catalysis benzene sulfonyl hydrazide containing iodine compound
Coupling reaction, the used catalyst containing iodine is cheap and easily-available, recycles simple and pollution-free.It through the invention can be with temperate condition
Lower high productivity realizes a series of benzenesulfonamides, wherein S-N key coupling reaction, in natural products, drug and
It all has broad application prospects in the synthesis of pesticide etc..
Specific embodiment
The following example will be helpful to understand the present invention, but the contents of the present invention are not limited thereto.
The synthesis of embodiment 1:1- (benzene sulfo group) pyrrolidines
By substrate 51.7mg (0.3mmol) benzene sulfonyl hydrazide and 42.7mg (0.6mmol) nafoxidine, catalyst 4.3mg
(0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF are added in 30mL tube sealing under air environment.Then
Tube sealing is put into 120 DEG C of oil baths and reacts 10h.After reaction, reaction solution is cooled to room temperature, 40mL saturated common salt is added
Water three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, and filtrate decompression is steamed
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after evaporating, obtains 57.7mg yellow oily liquid, yield
91%.
Gained liquid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.83 (d, J=8.0Hz, 2H), 7.60 (d, J=
8.0Hz, 1H), 7.54 (t, J=8.0Hz, 2H), 3.24 (t, J=8.0Hz, 4H), 1.74 (t, J=4.0Hz, 4H), carbon spectrum13C
NMR(101MHz,CDCl3) δ 136.69,132.55,128.95,127.31,47.86,25.09. and mass spectrum (molecular weight:
211.1) it analyzes and identifies, structural formula is
The synthesis of embodiment 2:1- ((4- fluorophenyl) sulfonyl) pyrrolidines
By substrate 57.4mg (0.3mmol) 4- fluorobenzene sulfohydrazide and 42.7mg (0.6mmol) nafoxidine, catalyst
30mL tube sealing is added in 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
In.Then tube sealing is put into 120 DEG C of oil baths and reacts 6h.After reaction, reaction solution is cooled to room temperature, 40mL saturation is added
Saline solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, and filtrate subtracts
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after pressure distillation, obtains 62.2mg white solid, yield is
90%.
Obtained solid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.79-7.76 (m, 2H), 7.14 (t, J=8.0Hz,
2H), 3.15 (t, J=8.0Hz, 4H), 1.78 (t, J=4.0Hz, 4H), carbon spectrum13C NMR(101MHz,CDCl3)δ166.28,
163.75,133.06,133.03,130.09,129.99,116.30,116.08,47.91,2 5.15. and mass spectrum (molecular weight:
229.1) it analyzes and identifies, structural formula is
The synthesis of embodiment 3:4- (sulfonyl -1- pyrrolidinyl) benzonitrile
By substrate 59.5mg (0.3mmol) 4- cyano benzene sulfonyl hydrazide and 42.7mg (0.6mmol) nafoxidine, catalyst
30mL tube sealing is added in 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
In.Then tube sealing is put into 100 DEG C of oil baths and reacts 10h.After reaction, reaction solution is cooled to room temperature, it is full that 40mL is added
And saline solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, filtrate
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after vacuum distillation, obtains 60.5mg white solid, yield
It is 91%.
Obtained solid is composed through hydrogen1H NMR(400MHz,CDCl3): δ 7.85 (d, J=8.0Hz, 2H), 7.53 (d, J=
4.0Hz, 2H), 3.26-3.21 (m, 4H), 1.13 (t, J=4.0Hz, 4H), carbon spectrum13C NMR(101MHz,CDCl3): δ
140.26,138.34,128.51,99.53,42.16,14.25,1.12. and mass spectrum (molecular weight: 239.1) analyzing and identifying, knot
Structure formula is
The synthesis of embodiment 4:1- tosyl pyrrolidines
By substrate 55.9mg (0.3mmol) 4- Methyl benzenesulfonyl hydrazine and 42.7mg (0.6mmol) nafoxidine, catalyst
30mL tube sealing is added in 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
In.Then tube sealing is put into 80 DEG C of oil baths and reacts 15h.After reaction, reaction solution is cooled to room temperature, 40mL saturation is added
Saline solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, and filtrate subtracts
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after pressure distillation, obtains 64.2mg white solid, yield is
95%.
Obtained solid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.71 (d, J=8.0Hz, 2H), 7.31 (d, J=
8.0Hz, 2H), 3.22 (t, J=8.0Hz, 4H), 2.43 (s, 3H), 1.75 (d, J=4.0Hz, 4H), carbon spectrum13C NMR
(101MHz,CDCl3) δ 143.30,133.75,129.58,127.46,47.87,25.11,21.43. and mass spectrum (molecular weight:
225.1) it analyzes and identifies, structural formula is
The synthesis of embodiment 5:4- ((4- methoxyphenyl) sulfonyl) morpholine
By substrate 60.6mg (0.3mmol) 4- methoxybenzene sulfohydrazide and 52.3mg (0.6mmol) morpholine, catalyst
30mL tube sealing is added in 4.3mg (0.03mmol) iodate amine, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
In.Then tube sealing is put into 100 DEG C of oil baths and reacts 12h, after reaction, reaction solution is cooled to room temperature, it is full that 40mL is added
And saline solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, filtrate
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after vacuum distillation, obtains 65.6mg white solid, yield
It is 85%.
Obtained solid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.69 (d, J=8.0Hz, 2H), 7.02 (d, J=
8.0Hz, 2H), 3.88 (s, 3H), 3.73 (s, 4H), 2.97 (s, 4H), carbon spectrum13C NMR(101MHz,CDCl3)δ163.16,
129.90,126.36,114.25,65.95,55.62,45.95. and mass spectrum (molecular weight: 257.1) analyzing and identifying, structural formula
For
The synthesis of embodiment 6:N, N- dibenzyl -4- methoxybenzenesulphoismide
By substrate 60.6mg (0.3mmol) 4- methoxybenzene sulfohydrazide and 118.4mg (0.6mmol) dibenzylamine, catalysis
30mL envelope is added in agent 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
Guan Zhong.Then tube sealing is put into 120 DEG C of oil baths and reacts 10h.After reaction, reaction solution is cooled to room temperature, 40mL is added
Saturated salt solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, filter
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after liquid vacuum distillation, obtains 97.0mg yellow solid, is produced
Rate is 88%.
By obtained solid through hydrogen spectrum (1H NMR(400MHz,CDCl3) δ 7.70 (d, J=8.0Hz, 2H), 7.30 (d, J=
8.0Hz, 1H), 7.27 (d, J=8.0Hz, 1H), 7.23 (d, J=8.0Hz, 1H), 7.13 (s, 3H), 6.99 (s, 4H), 6.89
(d, J=8.0Hz, 2H), 4.23 (s, 4H), 3.80 (s, 3H)), carbon spectrum (13C NMR(101MHz,CDCl3)δ162.89,
135.85,132.47,129.44,128.68,128.52,127.72,114.33,55.75,5 0.57.) and mass spectrum (molecular weight:
367.1) it analyzes and identifies, structural formula is
The synthesis of embodiment 7:N- ethyl -4- Methoxy-N-phenyl benzsulfamide
By substrate 60.6mg (0.3mmol) 4- methoxybenzene sulfohydrazide and 7.3mg (0.6mmol) N-ethylaniline, urge
Agent 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF, are added 30mL under air environment
In tube sealing.Then tube sealing is put into 120 DEG C of oil baths and reacts 12h.After reaction, reaction solution is cooled to room temperature, is added
40mL saturated salt solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dry with anhydrous sodium sulfate, mistake
Filter separates (ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) through silica gel column chromatography after filtrate decompression distillation, obtains 81.3mg yellow oil
Shape liquid, yield 92%.
Gained liquid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.53 (d, J=8.0Hz, 2H), 7.31 (d, J=
4.0Hz, 3H), 7.05 (d, J=8.0Hz, 2H), 6.91 (d, J=8.0Hz, 2H), 3.86 (s, 3H), 3.62-3.57 (m, 2H),
1.07 (t, J=8.0Hz, 3H), carbon spectrum13C NMR(101MHz,CDCl3)δ162.92,139.10,130.29,129.90,
129.11 129.07,127.94,114.00,55.70,45.56,14.14. and mass spectrum (molecular weight: 291.1) analyzing and identifying,
Structural formula is
The synthesis of embodiment 8:1- ((4- methoxyphenyl) sulfonyl) piperidines
By substrate 60.6mg (0.3mmol) 4- methoxybenzene sulfohydrazide and 51.0mg (0.6mmol) piperidines, catalyst
30mL tube sealing is added in 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF under air environment
In.Then tube sealing is put into 120 DEG C of oil baths and reacts 10h.After reaction, reaction solution is cooled to room temperature, it is full that 40mL is added
And saline solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dried, filtered with anhydrous sodium sulfate, filtrate
(ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) is separated through silica gel column chromatography after vacuum distillation, obtains 73.5mg yellow solid, yield
It is 96%.
Obtained solid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.68 (d, J=8.0Hz, 2H), 7.01 (d, J=
8.0Hz, 2H), 3.87 (s, 3H), 2.95 (t, J=4.0Hz, 4H), 1.63 (t, J=4.0Hz, 4H), 1.42 (d, J=4.0Hz,
2H), carbon is composed13C NMR(101MHz,CDCl3)δ162.80,129.63,127.64,114.05,55.56,46.87,25.06,
23.40. (molecular weight: 255.1) analyzing and identifying, and structural formula is with mass spectrum
The synthesis of embodiment 9:4- methoxy-. N-methyl-N- propylbenzenesulfonamide
By substrate 60.6mg (0.3mmol) 4- methoxybenzene sulfohydrazide and 43.9mg (0.6mmol) N methyl pmpyl amine, urge
Agent 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF, are added 30mL under air environment
In tube sealing.Then tube sealing is put into 120 DEG C of oil baths and reacts 10h.After reaction, reaction solution is cooled to room temperature, is added
40mL saturated salt solution three times with the extraction of 100mL ethyl acetate merges organic layer.Organic layer is dry with anhydrous sodium sulfate, mistake
Filter separates (ethyl acetate/petroleum ether: 1/2 makees eluant, eluent) through silica gel column chromatography after filtrate decompression distillation, obtains 69.3mg yellow oil
Shape liquid, yield 95%.
Gained liquid is composed through hydrogen1H NMR(400MHz,CDCl3) δ 7.61 (d, J=8.0Hz, 2H), 6.90 (d, J=8.0Hz,
2H), 3.76 (s, 3H), 2.84 (t, J=8.0Hz, 2H), 2.59 (s, 3H), 1.49-1.40 (m, 2H), 0.82 (t, J=4.0Hz,
3H), carbon is composed13C NMR(101MHz,CDCl3)δ162.71,129.33,129.10,114.13,55.55,51.70,34.50,
20.81,11.00. and mass spectrum (molecular weight: 243.1) analyzing and identifying, and structural formula is
Claims (7)
1. a kind of method that benzene sulfonyl hydrazide analog derivative synthesizes benzenesulfonamides without metal catalytic with secondary amine, feature
It is, this method is under air environment, using benzene sulfonyl hydrazide analog derivative and secondary amine as substrate, containing iodine compound as catalysis
Agent, tert-butyl hydroperoxide are oxidant, and S-N key coupling reaction occurs in a solvent, generate benzenesulfonamides；Its
In, the general formula of benzene sulfonyl hydrazide analog derivative isR1For hydrogen, halogen or substituent group.
2. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that the substituent group be methyl, cyano or methoxyl group.
3. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that the secondary amine be nafoxidine, morpholine, dibenzylamine, N-ethylaniline, piperidines or N- methyl-prop
Amine.
4. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that it is described containing iodine compound be KI, NH4I or tetrabutylammonium iodide.
5. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that the solvent be THF, toluene, CH3CN or DMF.
6. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that the benzene sulfonyl hydrazide analog derivative, secondary amine, the molar ratio of catalyst and oxidant are 1:2:
0.1:0.5。
7. benzene sulfonyl hydrazide analog derivative as described in claim 1 synthesizes benzenesulfonamides without metal catalytic with secondary amine
Method, which is characterized in that the reaction temperature be 80-120 DEG C, time 6-15h.
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Citations (2)
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| CN107043340A (en) * | 2017-05-02 | 2017-08-15 | 重庆锦杉科技有限公司 | A kind of method prepared to chlorobenzenesulfonyl hydrazine |
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2018
- 2018-10-24 CN CN201811240921.XA patent/CN109020844A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107043340A (en) * | 2017-05-02 | 2017-08-15 | 重庆锦杉科技有限公司 | A kind of method prepared to chlorobenzenesulfonyl hydrazine |
| CN106938977A (en) * | 2017-05-03 | 2017-07-11 | 李博强 | A kind of preparation method of unifor |
Non-Patent Citations (4)
| Title |
|---|
| ALEXANDER O. TERENT"EV ET AL: "Electrochemical synthesis of sulfonamides from arenesulfonohydrazides or sodium p-methylbenzenesulfinate and amines", 《MENDELEEV COMMUN》 * |
| HUI YU ET AL: "NH4I-Catalyzed Synthesis of Sulfonamides from Arylsufonylhydrazides and Amines", 《CHIN. J. CHEM.》 * |
| SANTOSH KUMAR REDDY PARUMALA ET AL: "Metal-free synthesis of sulfonamides via iodine-catalyzed oxidative coupling of sulfonyl hydrazides and amines", 《TETRAHEDRON LETTERS》 * |
| SIRILATA YOTPHAN ET AL: "Iodine-catalyzed expeditious synthesis of sulfonamides from sulfonyl hydrazides and amines", 《ORG. BIOMOL. CHEM.》 * |
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