CN105131019A - Benzothiazopyridine derivative and preparation method therefor - Google Patents
Benzothiazopyridine derivative and preparation method therefor Download PDFInfo
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- CN105131019A CN105131019A CN201510524093.2A CN201510524093A CN105131019A CN 105131019 A CN105131019 A CN 105131019A CN 201510524093 A CN201510524093 A CN 201510524093A CN 105131019 A CN105131019 A CN 105131019A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a benzothiazopyridine derivative and a preparation method therefor. The structural formula of the benzothiazopyridine derivative is shown in the description. The preparation method comprises: carrying out a reaction on arylamine and pyridine disulfide in a reaction solvent in the presence of a ferrum reagent and an iodine reagent to obtain the target benzothiazopyridine compound. The preparation method disclosed by the invention synthesizes the derivative by one step reaction and is simple to operate and mild in reaction condition, and the raw materials are cheap and are easily available, so that the preparation method has a good market application prospect.
Description
Technical field
The invention belongs to organic chemical synthesis technical field, be specifically related to a kind of benzothiazine and pyridine derivate and preparation method thereof.
Background technology
Thiazides compounds is widely used in medicine, agricultural, the field such as photoelectric material and coating.People's (United States Patent (USP): US6583138B1) researchs such as Miyamoto in 2003 find benzothiazine and pyridine compounds and their has good activity to histamine, leukotrienes etc., anaphylactic disease such as asthma, rhinitis, irritable bowel can be treated, the disease such as atopic dermatitis and measles.Traditionally, thiazides compounds is generally at high temperature synthesized by pentanoic and sulphur compound and obtains.The shortcoming of this method is when reaction substrate contains substituting group, and reaction preference is not good has isomer generation, difficult separation.In addition, also can pass through four-step reaction, synthesize this compounds by rearrangement reaction, but multi-step reaction increases synthesis difficulty and cost, and the regioselectivity containing substituent substrate reactions is poor.2008,
deng people with being with the bromo-2-iodobenzene of substituent 1-, primary amine, 2-bromo thiophenol has synthesized the thiazides compounds that N-replaces under catalyzing by metal palladium, but multiple reaction site limits the expansion of its substitutive derivative, and palladium metal expensive reagents is unfavorable for industrial applications.Afterwards, the people such as Ma have developed a kind of C-S of CuI/L-Proline-Catalyzed, C-N linked reaction, with 2-Iodoaniline, 2-bromo thiophenol is that starting raw material synthesis contains substituent thiazides compounds, and the deficiency of this method is that reaction preference is poor, multiple by product is had to generate, and substrate spectrum is narrow, condition needs to control, and the time is long.Although the synthetic technology of thiazides compounds obtains certain development, the synthesis of pyrido thiazides compounds is but very rare.2012, Zeng report CuI catalysis without the C-S between dihaloaromatic compound adjacent under part condition and near amino thiophenols, C-N coupling forms the method for thiazine compounds, and adjacent dihaloaromatic compound and near amino thiophenols react to synthesize and obtain pyrido thiazides compounds by application the method.But adjacent dihalo aromatic hydrocarbons is difficult to obtain, and has larger toxicity.In the same year, Beresneva reports 2-aminobenzothiazole and 2,3-dibromo pyridine reacts the benzothiazine the method for pyridine that generate, and this reaction needs highly basic and part to be started, and temperature of reaction is high, and generates two kinds of different benzothiazines and pyridine, and productive rate is low.From the technological method of the synthesis thiazides compounds of development at present, starting raw material used is almost the aromatic hydrocarbons of single halo or two halo, and well-known halogenated aryl hydrocarbon is a kind of carcinogenic aromatic hydroxy compound, and unfriendly to environment, Atom economy is not high.
Therefore, for the foregoing reasons, need a kind of cheap economy of development, without the need to using precious metal, without the need to using halogenated aryl hydrocarbon for raw material, pyridine synthesis the technological method of thiazine derivative, and prepare multifarious pyrido thiazine derivative for new drug initiative and material science starting material are provided, this is the power place that the present invention is accomplished.
Summary of the invention
The object of this invention is to provide a kind of efficient, benzothiazine that safety, green syt one class are novel and the technological method of pyridine derivate, solve hydrocarbon functionalization direct construction benzothiazine and the technical barrier of pyridine derivate.
The present invention realizes especially by following technical scheme:
A kind of benzothiazine pyridine derivate, its structural formula is such as formula shown in I:
Wherein, R
1be selected from C
1-C
6alkyl, C
1-C
6alkoxyl group, halogen or phenyl;
R
2be selected from H, C
1-C
6alkyl, C
1-C
6alkoxy or halogen;
R
3be selected from C
1-C
6alkyl;
R
4be selected from H, C
1-C
6alkyl, halogen, C
1-C
6alkoxyl group.
Described C
1-C
6the implication of alkyl refers to the straight or branched alkyl with 1-6 carbon atom, that includes C
1alkyl, C
2alkyl, C
3alkyl, C
4alkyl, C
5alkyl or C
6alkyl, such as can be methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl or alkane hexyl etc. in non-limiting manner.
Described C
1-C
6alkoxyl group refers to above-mentioned C
1-C
6group after alkyl is connected with O atom.
Described halogen obtains implication and refers to haloid element, non-exclusively such as can be F, Cl, Br or I.
Present invention also offers the synthetic method of described benzothiazine pyridine derivate, in order to create benzothiazine and pyridine derivate and technology of preparing thereof, seek to be applicable to benzothiazine and the technological method of pyridine derivate synthesis, present inventor has performed deep research, after having paid a large amount of creative works, research has found at I
2/ FeF
3under the catalysis of system, effectively can build C-S key and C-N key by activated carbon hydrogen bond, a step builds benzothiazine and pyridine derivate.This method is simple to operate, and compatible with multiple functional group, Atom economy is high, and productive rate is medium, is a kind ofly effectively to prepare benzothiazine and the effective ways of pyridine derivate.
Concrete a kind of benzothiazine the synthetic method of pyridine derivate, under the existence of ferron and iodine reagent, the arylamine of through type (II) and the pyridine disulfide of formula (III) react in reaction solvent, thus the benzothiazine of obtained formula (I) pyridine compounds, its reaction scheme is:
In described synthetic method of the present invention, formula (II) is 1:0.5-1 with the mol ratio of formula (III) compound, can be such as 1:0.5,1:0.6,1:0.7,1:0.8,1:0.9 or 1:1 in non-limiting manner.
In described synthetic method of the present invention, the mol ratio of formula (II) compound and ferron and iodine reagent is 1:0-0.2:0.05-1, can be such as 1:0.05:0.05,1:0.1:0.1,1:0.15:0.15 or 1:0.2:0.2 in non-limiting manner.
In described synthetic method of the present invention, described iodine reagent is elemental iodine, N-N-iodosuccinimide or iodine chloride.
In described synthetic method of the present invention, described ferron is the arbitrary combination of borontrifluoride iron, iron trichloride, ferric bromide, ferric sulfate, ferrous sulfate, iron acetate and their hydrate thereof, most preferably is borontrifluoride iron.
In described synthetic method of the present invention, reaction solvent when formula (II) and (III) react is organic solvent, can be such as Nitromethane 99Min., 1 in non-limiting manner, 2-ethylene dichloride, chloroform, methylene dichloride, toluene, acetonitrile, N, in dinethylformamide (DMF), ethanol, dimethyl sulfoxide (DMSO) (DMSO), tetrahydrofuran (THF), tetracol phenixin, normal hexane, n-propyl alcohol, Virahol, butanols, amylalcohol, acetone, 2-butanone etc. any one or multiple, most preferably be Nitromethane 99Min..
In described synthetic method of the present invention, temperature of reaction is 50-140 DEG C, non-exclusively can be such as 50 DEG C, 60 DEG C, 70 DEG C, 80 DEG C, 90 DEG C, 100 DEG C, 110 DEG C, 120 DEG C, 130 DEG C or 140 DEG C.
In described synthetic method of the present invention, reaction times, there is no particular limitation, such as can detect the residual quantity of raw material by gas chromatograph-mass spectrometer or TLC how many and determine the suitable reaction times, it typically is 4-48 hour, is such as 4 hours, 6 hours, 8 hours, 12 hours, 18 hours, 24 hours, 36 hours or 48 hours in non-limiting manner.
In described synthetic method of the present invention, aftertreatment after reaction terminates can adopt any known conventional processing means, such as, any one process means in crystallization, column chromatography purification, extraction etc. or the combination of multiple process means in organic synthesis field.As a kind of exemplary aftertreatment means, can be such as: after completion of the reaction, with Rotary Evaporators from the mixture that obtains after reaction terminates except desolventizing, residue 300-400 order silica gel column chromatography is purified and is obtained target product, and column chromatography procedure can determine suitable wash-out terminal with TLC tracing and monitoring.
Beneficial effect of the present invention is: by using arylamine and pyridine disulfide to be raw material, and by using ferron and iodine reagent as the suitable selection of catalyzer and other processing parameter and combination, a step obtains benzothiazine and pyridine compounds.The plurality of advantages such as described method has reaction conditions gentleness, cheaper starting materials is easy to get, Atom economy is high, for novel benzothiazine and the preparation of pyridine compounds and their provides effective synthetic method.Forefathers study discovery benzothiazine and pyridine compounds and their has good activity to histamine, leukotrienes etc., anaphylactic disease such as asthma, rhinitis, irritable bowel can be treated, the disease such as atopic dermatitis and measles, therefore has good researching value and application prospect.
Embodiment
Below in conjunction with embodiment, the present invention is described further, the following stated, only to preferred embodiment of the present invention, not do other forms of restriction to the present invention, any those skilled in the art may utilize the technology contents of above-mentioned announcement to be changed to the Equivalent embodiments of equal change.Everyly do not depart from the present invention program's content, any simple modification done following examples according to technical spirit of the present invention or equivalent variations, all drop in protection scope of the present invention.
The synthesis of embodiment 1 Compound I-1
Synthetic route is:
Specifically comprise the following steps:
By above formula (II-1) compound, formula (III-1) compound, borontrifluoride iron, elemental iodine mixing, make its mol ratio be 1:1:0.2:0.2, its Chinese style (II-1) compound is 2mmol.By reaction system stirring reaction 4 hours at 100 DEG C.Reaction terminates rear cooling, and with short silicagel column suction filtration, filtrate revolves steaming, remove unnecessary iodine, except desolventizing, residuum silica gel column chromatography, sherwood oil drip washing, TLC detects, merge the effluent liquid containing product, Rotary Evaporators distillation is except desolventizing, and vacuum-drying obtains the target product of yellow solid, productive rate 61%, purity is 99.3% (HPLC).
NMR (Nuclear Magnetic Resonance) spectrum:
1HNMR(500MHz,CDCl
3)δ7.98(d,J＝4.9Hz,1H),7.21(d,J＝7.4Hz,1H),6.72–6.66(m,3H),3.94–3.89(t,J＝6.3Hz,2H),2.70(t,J＝6.1Hz,2H),2.18(s,3H),2.04(p,J＝6.0Hz,2H)。
13CNMR(125MHz,CDCl
3)δ154.7,144.8,137.3,133.7,132.0,128.9,125.7,125.3,118.6,117.3,116.3,44.7,28.0,21.6,20.1。
The synthesis of embodiment 2 Compound I-2
Synthetic route is:
Specifically comprise the following steps:
By above formula (II-2) compound, formula (III-1) compound, borontrifluoride iron, elemental iodine mixing, make its mol ratio be 1:1:0.2:0.1, its Chinese style (II-2) compound is 2mmol.By reaction system stirring reaction 36 hours at 80 DEG C.Reaction terminates rear cooling, and with short silicagel column suction filtration, filtrate revolves steaming, remove unnecessary iodine, except desolventizing, residuum silica gel column chromatography, sherwood oil drip washing, TLC detects, merge the effluent liquid containing product, Rotary Evaporators distillation is except desolventizing, and vacuum-drying obtains the target product of yellow liquid, productive rate 63%, purity is 99.1% (HPLC).
NMR (Nuclear Magnetic Resonance) spectrum:
1HNMR(500MHz,CDCl
3)δ8.02(d,J＝4.8Hz,1H),7.28(s,1H),6.96(d,J＝8.2Hz,1H),6.90(s,1H),6.77–6.72(m,2H),3.43(s,3H),2.24(s,3H)。
13CNMR(125MHz,CDCl
3)δ154.6,144.1,140.7,133.0,131.5,127.2,126.3,119.7,116.4,116.1,113.5,32.3,19.2。
The synthesis of embodiment 3 Compound I-3
Synthetic route is:
Specifically comprise the following steps:
By above formula (II-3) compound, formula (III-1) compound, borontrifluoride iron, elemental iodine, make its mol ratio be 1:0.75:0.2:0.2, its Chinese style (II-3) compound is 2mmol.By reaction system stirring reaction 12 hours at 140 DEG C.Reaction terminates rear cooling, and with short silicagel column suction filtration, filtrate revolves steaming, remove unnecessary iodine, except desolventizing, residuum silica gel column chromatography, sherwood oil drip washing, TLC detects, merge the effluent liquid containing product, Rotary Evaporators distillation is except desolventizing, and vacuum-drying obtains the target product of yellow liquid, productive rate 50%, purity is 99.2% (HPLC).
NMR (Nuclear Magnetic Resonance) spectrum:
1HNMR(500MHz,CDCl
3)δ8.05(d,J＝4.9Hz,1H),7.28(d,J＝7.5Hz,1H),7.14–7.10(m,1H),7.06(d,J＝2.1Hz,1H),6.79(dd,J＝7.4,5.0Hz,1H),6.75(d,J＝8.7Hz,1H),3.42(s,3H)。
13CNMR(125MHz,CDCl
3)δ155.1,145.5,142.9,134.3,128.0,127.5,126.4,122.8,118.0,116.4,115.4,33.5。
The synthesis of embodiment 4 Compound I-4
Synthetic route is:
Specifically comprise the following steps:
By above formula (II-2) compound, formula (III-4) compound, borontrifluoride iron, elemental iodine, make its mol ratio be 1:1:0.2:0.2, its Chinese style (II-2) compound is 2mmol.By reaction system stirring reaction 24 hours at 80 DEG C.Reaction terminates rear cooling, and with short silicagel column suction filtration, filtrate revolves steaming, remove unnecessary iodine, except desolventizing, residuum silica gel column chromatography, sherwood oil drip washing, TLC detects, merge the effluent liquid containing product, Rotary Evaporators distillation is except desolventizing, and vacuum-drying obtains the target product of safran solid, productive rate 64%, purity is 99.2% (HPLC).
NMR (Nuclear Magnetic Resonance) spectrum:
1HNMR(500MHz,CDCl
3)δ7.14(d,J＝7.5Hz,1H),6.93(d,J＝8.2Hz,1H),6.89(s,1H),6.72(d,J＝8.2Hz,1H),6.58(t,J＝10.9Hz,1H),3.42(s,3H),2.39(s,3H),2.22(s,3H)。
13CNMR(125MHz,CDCl
3)δ154.9,154.3,142.0,134.3,132.2,128.0,127.3,121.1,116.6,114.5,113.1,33.2,23.9,20.2。
The synthesis of embodiment 5 Compound I-5
Synthetic route is:
Specifically comprise the following steps:
By above formula (II-2) compound, formula (III-5) compound, borontrifluoride iron, elemental iodine, make its mol ratio be 1:1:0.2:0.2, its Chinese style (II-2) compound is 2mmol.By reaction system stirring reaction 26 hours at 80 DEG C.Reaction terminates rear cooling, and with short silicagel column suction filtration, filtrate revolves steaming, remove unnecessary iodine, except desolventizing, residuum silica gel column chromatography, sherwood oil drip washing, TLC detects, merge the effluent liquid containing product, Rotary Evaporators distillation is except desolventizing, and vacuum-drying obtains the target product of yellow solid, productive rate 55%, purity is 99.2% (HPLC).
NMR (Nuclear Magnetic Resonance) spectrum:
1HNMR(500MHz,CDCl
3)δ7.93(d,J＝1.9Hz,1H),7.22(d,J＝2.0Hz,1H),6.96(d,J＝8.1Hz,1H),6.87(s,1H),6.73(d,J＝8.2Hz,1H),3.39(s,3H),2.24(s,3H)。
13CNMR(125MHz,CDCl
3)δ153.9,143.0,141.2,133.3,132.9,128.5,127.4,124.6,119.8,118.8,114.7,33.4,20.2。
Claims (10)
1. benzothiazine a pyridine derivate, it is characterized in that, its general structure is such as formula shown in I:
Wherein, R
1be selected from C
1-C
6alkyl, C
1-C
6alkoxyl group, halogen or phenyl;
R
2be selected from H, C
1-C
6alkyl, C
1-C
6alkoxy or halogen;
R
3be selected from C
1-C
6alkyl;
R
4be selected from H, C
1-C
6alkyl, halogen, C
1-C
6alkoxyl group.
2. a kind of benzothiazine according to claim 1 pyridine derivate, is characterized in that, described C
1-C
6alkyl is the straight or branched alkyl with 1-6 carbon atom, comprises C
1alkyl, C
2alkyl, C
3alkyl, C
4alkyl, C
5alkyl or C
6alkyl.
3. a kind of benzothiazine according to claim 1 pyridine derivate, is characterized in that, described C
1-C
6alkoxyl group is C
1-C
6group after alkyl is connected with O atom.
4. a kind of benzothiazine according to claim 1 pyridine derivate, it is characterized in that, described halogen is haloid element.
5. benzothiazine described in claim 1 synthetic method of pyridine derivate, it is characterized in that, under the existence of ferron and iodine reagent, the arylamine of through type II and the pyridine disulfide of formula III react in reaction solvent, thus the benzothiazine of obtained formula I pyridine compounds, its reaction scheme is:
6. synthetic method according to claim 5, is characterized in that, the mol ratio of formula II and formula III compound is 1:0.5-1.
7. synthetic method according to claim 5, is characterized in that, the mol ratio of formula II compound and ferron and iodine reagent is 1:0-0.2:0.05-1.
8. the synthetic method according to claim 5 or 7, is characterized in that, described iodine reagent is elemental iodine, N-N-iodosuccinimide or iodine chloride.
9. the synthetic method according to claim 5 or 7, is characterized in that, described ferron is borontrifluoride iron, iron trichloride, ferric bromide, ferric sulfate, ferrous sulfate or iron acetate.
10. synthetic method according to claim 5, is characterized in that, the temperature of reaction of reaction system is 50-140 DEG C.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114380848A (en) * | 2020-10-19 | 2022-04-22 | 华南农业大学 | Preparation and application of isoquinoline thiazole salt and derivatives thereof |
-
2015
- 2015-08-24 CN CN201510524093.2A patent/CN105131019A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| CHUAN DAI,ET AL.,: "Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C–S and C–N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols", 《CHEM. COMMUN.》 * |
| DAWEI MA,ET AL.,: "Assembly of Substituted Phenothiazines by a Sequentially Controlled CuI/l-Proline-Catalyzed Cascade C-S and C-N Bond Formation", 《ANGEW. CHEM. INT. ED.》 * |
| WEIYE HU,ET AL.,: "Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C−S/C−N Cross-Coupling Reaction", 《J. ORG. CHEM》 * |
| 魏亮等，: "C−H 硫化/胺化反应合成苯并噻嗪并吡啶衍生物的研究", 《中国化学会第九届全国有机化学学术会议》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114380848A (en) * | 2020-10-19 | 2022-04-22 | 华南农业大学 | Preparation and application of isoquinoline thiazole salt and derivatives thereof |
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