CN104447536B - Preparation method of N-2-quinolyl aryl sulfonamide compounds - Google Patents
Preparation method of N-2-quinolyl aryl sulfonamide compounds Download PDFInfo
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- CN104447536B CN104447536B CN201410579457.2A CN201410579457A CN104447536B CN 104447536 B CN104447536 B CN 104447536B CN 201410579457 A CN201410579457 A CN 201410579457A CN 104447536 B CN104447536 B CN 104447536B
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- quinoline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
Abstract
The invention belongs to the technical field of fine chemical engineering, and discloses a preparation method of N-2-quinolyl aryl sulfonamide compounds. The preparation method can be used for synthesizing a series of N-2-quinolyl aryl sulfonamide compounds from aryl sulfonamide and derivative of quinoline N-oxide by carrying out a heating reaction in an organic solvent with a trivalent iodine compound serving as an oxidant and triarylphosphine compounds functioning as additives. The invention mainly aims at providing a synthesis method of the N-2-quinolyl aryl sulfonamide compounds. The method is simple and efficient, high in atom economy and environment-friendly; the method has the advantages of being simple in method step, easy in obtaining of raw materials, high in atom economy, environment-friendly and the like. The N-2-quinolyl aryl sulfonamide, as an important skeleton structure, can be widely applied to the medicine synthesis field, and has high use value and social and economic benefits.
Description
Technical field
The present invention relates to a kind of preparation method of N-2- quinolyls arylsulfonamides compound, belongs to fine chemical technology
Field.
Background technology
N-2- quinolyl arylsulfonamides compounds be a class it is important with bioactive molecule, its framing structure frequency
It is numerous to come across in drug molecule, have a very wide range of applications in pharmaceutical synthesis field.With regard to N-2- quinolyl arylsulfonyls
The synthesis of aminated compoundss, generally adopts the following two kinds method：
(1) aryl sulfonic acid amides and 2- Bromoquinoline coupling reactions
The substrate of the method is expensive, need to be previously prepared, and environment is unfriendly, and Atom economy is low.[referring to：
Baffoe,Jonathan et al.Org.Lett.2010,12,1532.]。
(2) sulfonic acid chloride and 2- quinolin-2-ylamine coupling reactions
The substrate of the method is expensive, need to be previously prepared, and environment is unfriendly, and Atom economy is low.[referring to (a)
Uchikawa,Osamu et al.PCT Int.Appl.2008016131,07Feb 2008；(b)Edwards,Martin
Paul et al.PCT Int.Appl.,2005060963,07Jul 2005；(c)Jacobsen,Jennifer A.et
al.Journal of Medicinal Chemistry,2011,54,591-602；(d)Kokatla,Hari Prasad et
al.Org.Biomolecular Chemistry,2013,11,1179.]。
The content of the invention
In order to overcome the deficiencies in the prior art, it is an object of the present invention to provide a kind of N-2- quinolyls aryl sulfonic acid amides
The preparation method of class compound.The method has that method and step is simple, raw material is easy to get, Atom economy height, environmental friendliness etc. are excellent
Point.As N-2- quinolyl aryl sulfonic acid amides are the important framing structures of a class, have widely in pharmaceutical synthesis field
Using.
In order to realize foregoing invention purpose, in the presence of solving the problems, such as prior art, the technical scheme that the present invention takes
It is：A kind of preparation method of N-2- quinolyls arylsulfonamides compound, is spread out with aryl sulfonic acid amides and Quinoline N-Oxide
Biological is raw material, and with trivalent iodine compound as oxidant, triaryl phosphine compound is additive, is heated in organic solvent anti-
Should, synthesizing a series of N-2- quinolyls arylsulfonamides compounds, reaction equation is as follows：
In formula, the aryl sulfonic acid amides are selected from p-methylphenyl sulphonylamine, 4- chlorobenzene sulfonamides, 4- nitrobenzene sulfonamides or 4-
One kind in trifluoromethyl benzene sulfonamide；
The Quinoline N-Oxide derivant is selected from Quinoline N-Oxide, 4- methylquinolines nitrogen oxides or 6- methoxyl group quinolines
One kind in quinoline nitrogen oxides；
The one kind of iodonium compound oxidation agent in iodobenzene acetate or double (trifluoroacetyl epoxide) iodobenzenes；
The triaryl phosphine compound additive in triphenylphosphine or 4-N- morpholines-phenyl diphenylphosphine one
Kind；
The organic solvent is selected from ether, benzene, toluene, 1,4- dioxane, dimethyl sulfoxide, N, N- dimethyl formyls
Amine, methanol, ethanol, 1,2- dichloroethanes, n-butyl alcohol, dichloromethane, chloroform, hexamethylene, n-butyl ether, carbon tetrachloride, second
One or two mixed solvents in acetoacetic ester, petroleum ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran, acetone or acetonitrile.
A kind of preparation method of N-2- quinolyls arylsulfonamides compound, comprises the following steps：
A () is by aryl sulfonic acid amides, Quinoline N-Oxide derivant, the agent of iodonium compound oxidation and triaryl phosphine chemical combination
Thing additive is added sequentially in the Schlenk bottles of 25mL, then add refined organic solvent be placed in oil bath it is anti-
Should, at 20-130 DEG C, the response time is controlled in 7-30 hours, the aryl sulfonic acid amides and Quinoline N-Oxide for reaction temperature control
The mol ratio of derivant is 1.0：1.0th, the mol ratio of the aryl sulfonic acid amides and iodonium compound oxidation agent is 1.0：0.5-
4.0th, the mol ratio of the aryl sulfonic acid amides and triaryl phosphine compound additive is 1.0：0.5-4.0, the organic solvent
Addition be 10-100 times of aryl sulfonic acid amides quality；
B () reaction terminates after, organic solvent is removed under reduced pressure；
C () is obtained series N-2- quinolyl arylsulfonamides using petrol ether/ethyl acetate eluting, Jing silica gel post separation
Compound.
Present invention has the advantages that：A kind of preparation method of N-2- quinolyls arylsulfonamides compound, is with aryl
Sulfonamide and Quinoline N-Oxide derivant are raw material, and with trivalent iodine compound as oxidant, triaryl phosphine compound is to add
Plus agent, reacting by heating, synthesizes a series of N-2- quinolyls arylsulfonamides compounds in organic solvent.With prior art phase
Than, the present invention be mainly to provide it is a kind of it is simple efficiently, Atom economy is high, eco-friendly N-2- quinolyls arylsulfonyl amination
The synthetic method of compound, the method have that method and step is simple, raw material is easy to get, Atom economy high, advantages of environment protection.By
It is the important framing structure of a class in N-2- quinolyl aryl sulfonic acid amides, has a very wide range of applications in pharmaceutical synthesis field,
With larger use value and economic results in society.
Description of the drawings
Fig. 1 is compound 1a's1H-NMR。
Fig. 2 is compound 1a's13C-NMR。
Fig. 3 is compound 1b's1H-NMR。
Fig. 4 is compound 1b's13C-NMR。
Fig. 5 is compound 1c's1H-NMR。
Fig. 6 is compound 1c's13C-NMR。
Fig. 7 is compound 1d's1H-NMR。
Fig. 8 is compound 1d's13C-NMR。
Fig. 9 is compound 1e's1H-NMR。
Figure 10 is compound 1e's13C-NMR。
Figure 11 is compound 1f's1H-NMR。
Figure 12 is compound 1f's13C-NMR。
Specific embodiment
With reference to embodiment, the invention will be further described：
Embodiment 1：The synthesis of 4-Methyl-N- (quinolin-2-yl) benzenesulfonamide (1a)
Accurately weigh p-methylphenyl sulphonylamine (42.8mg, 0.25mmol), Quinoline N-Oxide (36.3mg,
0.25mmol), iodobenzene acetate (40.1mg, 0.125mmol), triphenylphosphine (32.8mg, 0.125mmol), and be added sequentially to
In the Schlenk bottles of 25mL, refined acetonitrile (0.50mL), 20 DEG C of reaction 8h are added.After reaction terminates, it is removed under reduced pressure molten
Agent, using petrol ether/ethyl acetate as eluant, silica gel post separation, 4-Methyl-N- (quinolin-2-yl)
The yield of benzenesulfonamide is 80%.1H NMR(400MHz,CDCl3)δ11.86(s,1H),7.90–7.85(m,
3H), 7.63-7.60 (m, 2H), 7.46 (d, J=8.5Hz, 1H), 7.37-7.34 (m, 1H), 7.26 (d, J=5.8Hz, 2H),
6.95 (d, J=9.4Hz, 1H), 2.39 (s, 3H)；13C NMR(101MHz,CDCl3)δ154.0,142.6,140.5,139.7,
136.3,131.5,129.2,127.9,126.1,124.5,121.2,120.9,117.2,21.3；IR(KBr)υ(cm-1)3425,
3337,3050,3024,1670,1601,1493,1475,1441,1382,1157,910,778,736,730,698；HRMS-EI
(m/z):[M+H]+Calculated for C16H14N2O2S,299.0854；found,299.0866.
Embodiment 2：The synthesis of 4-Nitro-N- (quinolin-2-yl) benzenesulfonamide (1c)
Accurately weigh 4- nitrobenzene sulfonamides (50.5mg, 0.25mmol), Quinoline N-Oxide (44.3mg,
0.25mmol), iodobenzene acetate (123.5mg, 0.5mmol), triphenylphosphine (17.9mg, 0.125mmol), and be added sequentially to
In the Schlenk bottles of 25mL, refined toluene (3.0mL) is added, is placed in 60 DEG C of oil baths and is reacted 7h.After reaction terminates, subtract
Pressure removes solvent, using petrol ether/ethyl acetate as eluant, silica gel post separation, 4-Nitro-N- (quinolin-2-yl)
The yield of benzenesulfonamide is 76%.1H NMR (400MHz, DMSO) δ 13.43 (s, 1H), 8.17 (d, J=
8.3Hz, 2H), 7.87 (d, J=7.9Hz, 1H), 7.74-7.70 (m, 1H), 7.64-7.57 (m, 5H), 7.44-7.40 (m,
1H)；13C NMR(101MHz,DMSO)δ148.4,141.8,131.6,131.4,130.9,130.8,128.2,128.1,
127.7,126.9,123.9,123.7,114.8；IR(KBr)υ(cm-1)3439,3326,2960,2921,2865,1653,
1492,1395,1378,1092,1015,908,837,771,758,734；HRMS(EI)Calculated for
C15H11N3O4S329.0470[M+],found 329.0478.
Embodiment 3：The synthesis of 4-Methyl-N- (quinolin-2-yl) benzenesulfonamide (1d)
Accurately weigh p-methylphenyl sulphonylamine (42.8mg, 0.25mmol), 4- methylquinoline nitrogen oxides (50.5mg,
0.25mmol), iodobenzene acetate (40.1mg, 0.125mmol), triphenylphosphine (32.8mg, 0.125mmol), and be added sequentially to
In the Schlenk bottles of 25mL, acetonitrile (2.50mL) and toluene (2.50mL) mixed solvent, 20 DEG C of reaction 8h are added.Reaction terminates
Afterwards, removal of solvent under reduced pressure, using petrol ether/ethyl acetate as eluant, silica gel post separation, 4-Methyl-N-
(quinolin-2-yl) yield of benzenesulfonamide is 80%.White solid (62.4mg, 40%yield),
mp 225-227℃.1H-NMR(d6-DMSO,400MHz):12.90 (bs, 1H), 7.86 (d, J=8.0Hz, 1H), 7.80 (d, J
=7.5Hz, 2H), 7.68-7.65 (m, 1H), 7.56 (d, J=8.1Hz, 1H), 7.42 (s, 1H), 7.38-7.33 (m, 3H),
2.57(s,3H),2.34(s,3H)；13C-NMR(d6-DMSO,101MHz):155.0,150.9,142.1,141.5,132.2,
129.8,126.6,125.5,124.4,121.6,118.8,118.2,115.4,21.4,19.7；IR(KBr)(cm-1)3442,
3198,2973,1629,1514,1396,1269,1138,908,838,677,615,555,475；HRMS-EI(m/z):[M]+
Calculated for C17H16N2O2S,312.0932；found,312.0930.
Embodiment 4：The conjunction of 4-Trifluoromethyl-N- (quinolin-2-yl) benzenesulfonamide (1e)
Into
Accurately weigh Quinoline N-Oxide (44.3mg, 0.25mmol), 4- trifluoromethyl benzene sulfonamides (55.0mg,
0.25mmol), double (trifluoroacetyl epoxide) iodobenzenes (107.2mg, 0.25mmol), 4-N- morpholines-phenyl diphenylphosphine
(100.9mg, 0.75mmol), and be added sequentially in the Schlenk bottles of 25mL, add refined dimethyl sulfoxide
(3.0mL), it is placed in 120 DEG C of oil baths and reacts 30h.After reaction terminates, removal of solvent under reduced pressure is made using petrol ether/ethyl acetate
For eluant, silica gel post separation, the receipts of 4-Trifluoromethyl-N- (quinolin-2-yl) benzenesulfonamide
Rate is 67%.1H NMR (400MHz, DMSO) δ 13.42 (s, 1H), 8.32 (d, J=9.5Hz, 1H), 8.13 (d, J=8.0Hz,
2H), 7.94 (d, J=8.2Hz, 2H), 7.87 (d, J=7.8Hz, 1H), 7.74-7.71 (m, 1H), 7.63-7.59 (m, 2H),
7.44–7.41(m,1H)；13C NMR(101MHz,DMSO)δ155.5,147.6,142.3,132.3,131.8,131.5,
128.4,127.0,126.2,125.0,124.5,122.3,121.2,115.5；IR(KBr)υ(cm-1)3421,3022,2956,
2923,2868,1670,1510,1466,1378,1157,1110,1021,817,756,744；HRMS(EI)Calculated
for C16H11N2O2F3S 352.0493[M+],found 352.0496.
Embodiment 5：The conjunction of N- (6-Methoxyquinolin-2-yl) -4-methylbenzenesulfonamide (1f)
Into
Accurately weigh p-methylphenyl sulphonylamine (42.8mg, 0.25mmol), 6- methoxy quinoline nitrogen oxides (44.0mg,
0.25mmol), iodobenzene acetate (320.8mg, 1.00mmol), triphenylphosphine (262.4mg, 1.00mmol), and be added sequentially to
In the Schlenk bottles of 25mL, acetonitrile (0.50mL), 20 DEG C of reaction 8h are added.After reaction terminates, removal of solvent under reduced pressure, using stone
Oily ether/ethyl acetate is used as eluant, silica gel post separation, N- (6-methoxyquinolin-2-yl) -4-
The yield of methylbenzenesulfonamide is 80%.White solid (131.3mg, 80%yield), mp 255-
257℃.1H-NMR(d6-DMSO,400MHz):7.97 (d, J=9.3Hz, 1H), 7.64 (d, J=7.4Hz, 2H), 7.46-7.43
(m, 2H), 7.38-7.36 (m, 2H), 7.13 (d, J=8.3Hz, 2H), 3.62 (s, 3H), 2.13 (s, 3H)；13C-NMR(d6-
DMSO,101MHz):155.7,141.8,133.2,132.2,132.0,131.5,131.4,129.2,128.8,128.7,
126.3,122.3,107.8,55.5,20.9；IR(KBr)(cm-1)3433,2916,1608,1393,1367,1269,1089,
954,816,722,663,585,543,467；HRMS-ESI(m/z):[M]+Calculated for C17H16N2O3S,
328.0882；found,328.0866.
Claims (2)
1. a kind of preparation method of N-2- quinolyls arylsulfonamides compound, it is characterised in that：With aryl sulfonic acid amides and quinoline
Quinoline nitrogen oxides derivant is raw material, and with trivalent iodine compound as oxidant, triaryl phosphine compound is additive, organic
Reacting by heating in solvent, synthesizes a series of N-2- quinolyls arylsulfonamides compounds, and reaction equation is as follows：
In formula, the aryl sulfonic acid amides are selected from p-methylphenyl sulphonylamine, 4- chlorobenzene sulfonamides, 4- nitrobenzene sulfonamides or 4- trifluoros
One kind in methyl benzenesulfonamide；
The Quinoline N-Oxide derivant is selected from Quinoline N-Oxide, 4- methylquinolines nitrogen oxides or 6- methoxy quinoline nitrogen
One kind in oxide；
The one kind of iodonium compound oxidation agent in iodobenzene acetate or double (trifluoroacetyl epoxide) iodobenzenes；
The one kind of the triaryl phosphine compound additive in triphenylphosphine or 4-N- morpholines-phenyl diphenylphosphine；
The organic solvent is selected from ether, benzene, toluene, 1,4- dioxane, dimethyl sulfoxide, N,N-dimethylformamide, first
Alcohol, ethanol, 1,2- dichloroethanes, n-butyl alcohol, dichloromethane, chloroform, hexamethylene, n-butyl ether, carbon tetrachloride, acetic acid second
One or two mixed solvents in ester, petroleum ether, methyl tertiary butyl ether(MTBE), tetrahydrofuran, acetone or acetonitrile.
2. a kind of preparation method of N-2- quinolyls arylsulfonamides compound according to claim 1, it is characterised in that
Comprise the following steps：
A aryl sulfonic acid amides, Quinoline N-Oxide derivant, the agent of iodonium compound oxidation and triaryl phosphine compound are added by ()
Plus agent is added sequentially in the Schlenk bottles of 25mL, then adds during refined organic solvent is placed in oil bath and react, instead
Answer temperature control at 20-130 DEG C, response time control is derived with Quinoline N-Oxide in 7-30 hours, the aryl sulfonic acid amides
The mol ratio of thing is 1.0：1.0th, the mol ratio of the aryl sulfonic acid amides and iodonium compound oxidation agent is 1.0：0.5-4.0、
The aryl sulfonic acid amides are 1.0 with the mol ratio of triaryl phosphine compound additive：0.5-4.0, the organic solvent plus
It is 10-100 times of aryl sulfonic acid amides quality to enter amount；
B () reaction terminates after, organic solvent is removed under reduced pressure；
C () is obtained series N-2- quinolyl arylsulfonamides chemical combination using petrol ether/ethyl acetate eluting, Jing silica gel post separation
Thing.
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| CN108329262A (en) * | 2018-02-07 | 2018-07-27 | 温州大学 | The synthetic method of N- (2- quinolyls) benzamide compound |
| CN108409652B (en) * | 2018-04-13 | 2020-05-05 | 中南大学 | Preparation method of ultrasonic-assisted N- (quinoline-2-yl) alkylamide |
| CN108373448B (en) * | 2018-04-23 | 2020-01-07 | 中南大学 | Microwave-assisted synthesis method of N- (quinoline-2-yl) aromatic amide |
| CN108610304B (en) * | 2018-06-19 | 2021-10-15 | 陕西师范大学 | Synthetic method of diaryl sultam compound |
| CN109485598A (en) * | 2018-11-29 | 2019-03-19 | 河南师范大学 | The new method of quinoline protecting group on a kind of removal amino |
| CN112724083B (en) * | 2021-01-06 | 2022-09-02 | 常州工学院 | Method for synthesizing secondary sulfonamide compound from benzamide compound and direct ortho-amine and application |
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| GB1166538A (en) * | 1967-06-10 | 1969-10-08 | Pfizer Ltd | Substituted Tetrahydroquinolines |
| AU541697B2 (en) * | 1979-11-19 | 1985-01-17 | Ici Australia Limited | Quinoline derivatives |
| AU710173B2 (en) * | 1996-07-19 | 1999-09-16 | Tularik Inc. | Pentafluorobenzenesulfonamides and analogs |
| MXPA02006474A (en) * | 1999-12-28 | 2002-11-29 | Eisai Co Ltd | Heterocyclic compounds having sulfonamide groups. |
| AU2009221285A1 (en) * | 2008-03-07 | 2009-09-11 | F. Hoffmann-La Roche Ag | 2-aminoquinoline derivatives as 5-HT ( 5A) receptor antagonists |
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