CN107629017A - A kind of [60] rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives - Google Patents
A kind of [60] rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives Download PDFInfo
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Abstract
The invention discloses a kind of [60] the rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives, belong to the synthesis technical field of fullerene derivate.Technical scheme main points are：A kind of FeCl2•4H2[60] rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives that O promotes, detailed process are：Using [60] fullerene and Weinreb acid amides as reaction raw materials, using internal oxidition strategy, pass through FeCl2•4H2The rich Le alkene oxazole derivative of relay cascade reaction synthesis [60] and [60] fowler 01 derivatives occur for O facilitation.The synthesis technique of the present invention has a wide application range of substrates, and chemo-selective is high, raw material is relative be easy to get and it is simple to operate the features such as.
Description
Technical field
The invention belongs to the synthesis technical field of fullerene derivate, and in particular to a kind of FeCl2·4H2[60] that O promotes
Richness strangles the synthetic method of alkene oxazole derivative and [60] fowler 01 derivatives.
Background technology
Iron is one of element most abundant in nature, and most of molysite is all nontoxic and environment amenable, and
And it is mostly cheap and easy to get, therefore the organic transformation for developing iron-based catalysis or promoting is very attractive.Past several
In 10 years, numerous effort have pointed to this target, and a series of reaction that iron-baseds promote has been developed.Corresponding molysite catalysis or
The reaction kinetic of the fullerene of promotion also result in significant concern.Early in 2002, domestic Gan Liangbing professors seminar reported
The radical reaction (formula 1) that [60] fullerene of road molysite or other metal salt catalysts occurs with tertbutanol peroxide, Gao Xuan
The oxygen-enriched more addition compound products of a kind of new fullerene are synthesized with selecting, and the reaction system are applied to C70In.
The synthesis of the oxygen-enriched derivative of the fullerene of formula 1
2008, the organic transformation that the military professor seminar of the officials of feudal dynasties first promotes ferric perchlorate was applied to the structure of fullerene
In modification, ferric perchlorate [Fe (ClO are systematically have studied4)3] in the presence of, fullerene and nitrile, aldehyde/ketone, substitution malonate, virtue
The radical reaction of ylboronic acid, beta-ketoester and acyl chlorides, it is prepared for a series of Bao Kuo oxazoles, 1,3- dioxolanes, fullerene
The miscellaneous derivative of different types of Fullerene Carbon including cyclized lactone, borate and 1,2- Fullerols etc..
The Matsuo research groups of Japan also reported the aryl halides and [60] fullerene of anhydrous ferric chloride promotion
More addition reactions, the reaction react at room temperature can realization in two hours in chlorobenzene and absolutely converted, and generate serial single
The polyarylated fullerene derivate of chloro, mainly based on the fowler ene product of six additions (formula 2), and according to reaction condition
Difference, the number of addition aryl can at most reach ten.
Then, they also found under the conditions of existing for anhydrous ferric trichloride, aliphatic carboxylic acid and aromatic carboxylic acid
To react generation 1 at room temperature with [60] fullerene, the Fullerol monoester derivates (formula 3) of 2- additions, and by further
Derivatization, hydroxyl can be further converted into ester or silicon ether, show that these secondary derivatives have very well through electrochemical research
Connect nucleophobic ability.
The synthesis of the more addition aryl substituted derivatives of the fullerene of formula 2
The synthesis of the 1,2- fowler 01 derivatives of formula 3 and derivatization
On the other hand, it is that functional group had both led using internal oxidition strategy in transition metal-catalyzed C-H priming reactions field
The reaction for making internal oxidation agent development again to group causes significant concern.This Critical policies not only eliminates reaction to outside
The demand of oxidant, while also improve the reactivity and selectivity and the convenience of operation of reaction.Wherein, N- methoxies
Yl-benzamide (ArCONHOMe) is anti-in the c h bond activation carried out using internal oxidition strategy as a kind of raw material cheap and easy to get
It is the substrate being frequently used in answering, and CONHOMe functional groups are to aoxidize homing device.It is however, relevant by N- methoxybenzenes
The report that formamide produces the synthesis application of amide groups free radical is seldom.Therefore, using cheap molysite, with ArCONHOMe
The new reaction pattern activated for substrate, the c h bond carried out using internal oxidition strategy, realizes that the more diversified fullerene of structure spreads out
The synthesis of biology is height requirement.
The content of the invention
Present invention solves the technical problem that there is provided, a kind of wide application range of substrates, chemo-selective are high and raw material is relative
FeCl simple and easy to get2·4H2[60] rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives that O promotes.
The present invention is to solve above-mentioned technical problem to adopt the following technical scheme that, a kind of FeCl2·4H2[60] fowler that O promotes
The synthetic method of alkene oxazole derivative and [60] fowler 01 derivatives, it is characterised in that detailed process is：With [60] fullerene and
Weinreb acid amides is reaction raw materials, using internal oxidition strategy, passes through FeCl2·4H2Relay cascade reaction occurs for O facilitation
Synthesize [60] rich Le alkene oxazole derivative and [60] fowler 01 derivatives；
The synthetic route of [60] the Fu Le alkene oxazole derivatives is：
Wherein R1For methoxyl group, to oxygen benzyl, acetyl group, benzoyl or ester group, R2For H or phenyl, R3For methyl, right
Methoxyl group, adjacent chlorine, m-chloro or to acetyl group.
The synthetic route of [60] the fowler 01 derivatives is：
Wherein R is to methoxyl group, adjacent methyl, to methyl, ester group, adjacent chlorine, m-chloro or H.
Further preferably, the specific synthesis step of described [60] Fu Le alkene oxazole derivatives is：First by [60] fullerene,
FeCl2·4H2O and N- methoxy benzamide derivatives are added in dry reaction tube, add o-dichlorohenzene and ultrasound makes
[60] fowler is completely dissolved, and then cock beyond the Great Wall is placed in stirring reaction in 80-110 DEG C of oil bath pan, reacts after terminating first with short
Pillar filters out salt and other insoluble matters, and decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first drenched with carbon disulfide
Wash pillar, then with carbon disulfide by the sample being spin-dried for all dissolving, loading, mistake post, first provide unreacted with carbon disulfide
[60] fowler, then with CS2/ DCM mixed liquors are that eluant, eluent carries out affording target product [60] Fu Le alkene oxazole derivative
Thing, described N- methoxy benzamide derivatives are
Further preferably, the specific synthesis step of described [60] fowler 01 derivatives is：First by [60] fullerene,
FeCl2·4H2O and N- methyl-N-methoxy heterocyclic carbamate derivatives are added in dry reaction tube, add o-dichlorohenzene
And ultrasound is completely dissolved [60] fullerene, then cock beyond the Great Wall is placed in stirring reaction in 90-110 DEG C of oil bath pan, reaction knot
Shu Houxian filters out salt and other insoluble matters with short column, adds triethylamine during filtering, then again with toluene elution pillar, finally
Decompression rotation remove solvent, with GF254 silica gel wet method dress posts, first with carbon disulfide elution pillar, will be then spin-dried for carbon disulfide
The whole dissolvings of sample, loading, post is crossed, first provide unreacted [60] fullerene with carbon disulfide, then with CS2/ DCM mixed liquors are made
Carry out affording target product [60] fowler 01 derivatives for eluant, eluent, the N- methyl-N-methoxies benzamide derives
Thing is
The present invention has developed a kind of new unique FeCl2·4H2The internal oxidition relay cascade reaction that O promotes synthesizes
[60] the rich new method for strangling alkene oxazole derivative and [60] fowler 01 derivatives.According to the difference of N- substituted radicals, [60] fowler
Benzyl hydroximic acid (Weinreb amides) or N- halobenzoyl amines the compound reaction that alkene substitutes with O- are respectively synthesized
[60] it is rich to strangle alkene oxazole derivative or [60] fowler 01 derivatives.The synthesis technique of the present invention has wide application range of substrates, changes
It is high to learn selectivity, raw material is relative be easy to get and it is simple to operate the features such as.
Embodiment
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The scope for inventing above-mentioned theme is only limitted to following embodiment, and all technologies realized based on the above of the present invention belong to this hair
Bright scope.
Embodiment 1
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methoxyl group-N- chlorobenzamides(18.5mg, 0.1mmol) then adds 4mL neighbour two in 15mLtube
Chlorobenzene, then closed are placed in 100 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first with the sub- mistake of short column
Salt and other insoluble matters are filtered, decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first elutes a pillar with carbon disulfide,
Then with as far as possible few carbon disulfide, by the sample being spin-dried for, all dissolving loading crosses post.First provided with carbon disulfide unreacted
[60] fullerene (22mg, 61%), then with CS2/ DCM=10/1 be eluant, eluent afford target product 2a (11.7mg,
28%).1H NMR(400MHz,CS2/CD3COCD3)δ8.41-8.40(m,2H),7.76-7.72(m,1H),7.70-7.66(m,
2H)。
Embodiment 2
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methoxyl group is to methyl benzamide(16.5mg, 0.1mmol) it is adjacent then to add 4mL in 15mLtube
Dichloro-benzenes, then closed are placed in 100 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first with short column
Salt and other insoluble matters are filtered out, then depressurizes rotation and removes solvent, with GF254 silica gel wet method dress posts, is first eluted one time with carbon disulfide
Pillar, then with as far as possible few carbon disulfide, by the sample being spin-dried for, all dissolving loading crosses post.First provided with carbon disulfide not anti-
[60] fullerene (24.5mg, 59%) answered, then with CS2/ DCM=10/1 is that eluant, eluent carries out affording target product 2b
(13.7mg, 31%).1H NMR(400MHz,CS2/CDCl3) δ 8.31 (d, J=8Hz, 2H), 7.41 (d, J=8Hz, 2H),
2.55(s,3H)。
Embodiment 3
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methoxyl group is to formic acid esters yl-benzamide(20.9mg, 0.1mmol) then adds in 15mLtube
Enter 4mL o-dichlorohenzenes, then closed are placed in 110 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first
Salt and other insoluble matters are filtered out with short column, decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first drenched with carbon disulfide
A pillar is washed, then all dissolving loading crosses post by the sample being spin-dried for as far as possible few carbon disulfide.First given with carbon disulfide
Go out unreacted [60] fullerene (20.9mg, 58%), then with CS2/ DCM=5/1 is that eluant, eluent carries out affording target production
Thing 2c (14.8mg, 33%).1H NMR(400MHz,CS2/CDCl3) δ 8.51 (d, J=8.4Hz, 2H), 8.26 (d, J=
8.4Hz,2H),3.98(s,3H)13C NMR(100MHz,CS2/CDCl3with Cr(acac)3as
relaxationreagent,all 2C unless indicated)165.12(1C),164.42(1C),147.85,
147.43,147.20,146.05,145.91,145.75,145.70,145.45,145.18,145.05,144.87,144.77,
144.38,144.20,143.89,142.85,142.46,142.41,142.35,142.01,141.92,141.78,141.65,
141.58,140.12,139.31,137.48,135.87,133.28,130.47,129.66,128.90,97.29(sp3-C of
C60),91.82(sp3-C of C60),51.88(1C)；FT-IRν/cm-1(KBr)2945,2839,1727,1643,1573,
1519,1433,1406,1382,1276,1103,1089,982,931,777,705,526,459；UV-vis(CHCl3)λmax/
nm 256,317,413,684；MALDI-TOF MS m/z calcdfor C69H7NO3[M+]897.0426,found
897.0420。
Embodiment 4
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methyl-N-methoxy benzamide(16.5mg, 0.1mmol) it is adjacent then to add 4mL in 15mLtube
Dichloro-benzenes, then closed are placed in 100 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first with short column
Filter out salt and other insoluble matters, to add a small amount of triethylamine during filtering, because product adsorbs on pillar, then again with toluene
Pillar is eluted, finally decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first elutes a pillar with carbon disulfide, then uses
By the sample being spin-dried for, all dissolving loading crosses post to few carbon disulfide as far as possible.First unreacted [60] fowler is provided with carbon disulfide
Alkene (20.9mg, 58%), then with CS2/ DCM=2/1 as eluant, eluent afford target product 2d (14.9mg,
33%).1H NMR(400MHz,CS2/CDCl3)δ7.94(m,2H),7.95-7.93(m,2H),7.61-7.57(m,3H),5.71
(s,1H),4.07(s,3H)；13C NMR(100MHz,CS2/CDCl3with Cr(acac)3asrelaxation reagent,
all 1C unless indicated)176.58(1C),152.48,151.57,149.64,148.75,148.05,147.95,
146.15,146.05,146.03,146.02,145.99,145.85,145.81,145.78,145.74,145.73,145.62,
145.60,145.54,145.38,145.31,145.29,145.27,145.05,144.93,144.82,144.77,144.51,
144.44,144.43,144.38,144.04,142.61,142.40,142.36,142.33,142.24,142.13,142.10,
142.02,141.91,141.88,141.66,141.46,141.13,141.01,140.95,140.87,140.80,140.59,
139.54,139.33,139.29,138.95,138.75,137.30,137.14,135.47,134.20,131.41,128.73
(2C),128.44(2C),86.19(sp3-Cof C60),77.93(sp3-C of C60),41.43；FT-IRν/cm-1(KBr)
2909,2843,1626,1463,1431,1363,1217,1051,1035,1024,988,574,526；UV-vis(CHCl3)λ
max/nm 263,317,416,688；MALDI-TOF MS m/z calcd for C68H9NO2Na[M+Na]+894.0526,
found 871.0524。
Embodiment 5
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methyl-N-methoxy is to methyl benzamide(17.9mg, 0.1mmol) then adds in 15mLtube
Enter 4mL o-dichlorohenzenes, then closed are placed in 100 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first
Salt and other insoluble matters are filtered out with short column, to add a small amount of triethylamine during filtering, because product adsorbs on pillar, then
Again with toluene elutes pillar, and finally decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first elutes a post with carbon disulfide
Son, then with as far as possible few carbon disulfide, by the sample being spin-dried for, all dissolving loading crosses post.First unreacted is provided with carbon disulfide
[60] fullerene (19.8mg, 55%), then with CS2/ DCM=2/1 is that eluant, eluent carries out affording target product 2e
(15.2mg, 35%).1H NMR(400MHz,CS2/CDCl3) δ 7.85 (d, J=8Hz 2H), 7.36 (d, J=8Hz, 2H),
5.78(s,1H),4.08(s,3H),2.5(s,3H)；13C NMR(100MHz,CS2/CDCl3with Cr(acac)3asrelaxation reagent,all 1C unless indicated)177.21,152.82,151.78,150.00,
149.13,148.35,148.24,146.45,145.43,146.34,146.30,146.10,146.07,146.04,146.01,
145.90,145.81,145.66,145.58,145.54,145.34,145.26,145.22,145.12,145.06,144.81,
144.79,144.72,144.68,144.34,142.68,142.65,142.61,142.53,142.52,142.44,142.42,
142.38,142.30,142.26,142.20,142.17,141.94,141.74,141.41,141.34,141.24,141.19,
141.10,140.87,139.74,139.61,139.56,139.23,139.04,137.57,137.37,135.85,131.45,
129.33(3C),129.20(3C),86.50(sp3-C of C60),78.29(sp3-C of C60),41.96,21.65；FT-IR
ν/cm-1(KBr),2916,2842,1622,1572,1519,1463,1431,1377,1361,1277,1050,1036,1021,
988,930,832,767,526,459；UV-vis(CHCl3)λmax/nm264,318,420,689；MALDI-TOF MS m/z
calcd for C69H11NO2Na[M+Na]+908.0682,found908.0677。
Embodiment 6
Accurately weigh [60] fullerene (36.0mg, 0.05mmol), Iron dichloride tetrahydrate (20.0mg, 0.1mmol), N-
Methyl-N-methoxy is to methoxy benzamide(19.5mg, 0.1mmol) in 15mLtube, then
4mL o-dichlorohenzenes are added, then closed are placed in 90 DEG C of oil bath of tube is reacted 2h by ultrasound to dissolving, after reaction terminates, first
Salt and other insoluble matters are filtered out with short column, to add a small amount of triethylamine during filtering, because product adsorbs on pillar, then
Again with toluene elutes pillar, and finally decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first elutes a post with carbon disulfide
Son, then with as far as possible few carbon disulfide, by the sample being spin-dried for, all dissolving loading crosses post.First unreacted is provided with carbon disulfide
[60] fullerene (20.9mg, 58%), then with CS2/ DCM=2/1 is that eluant, eluent carries out affording target product 2f
(14.9mg, 33%).1H NMR(400MHz,CS2/CDCl3) δ 7.98 (d, J=8Hz 2H), 7.08 (d, J=8Hz, 2H),
5.89(s,1H),4.08(s,3H),4.15(s,3H),3.96(s,3H)；13C NMR(100MHz,CS2/CDCl3with Cr
(acac)3as relaxation reagent,all 1C unless indicated)176.98,162.49,152.93,
151.80,150.08,149.28,148.38,148.27,146.48,146.45,146.35,146.32,146.12,146.09,
146.07,146.03,145.93,145.81,145.68,145.61,145.59,145.57,145.54,145.36,145.24,
145.14,145.08,144.86,144.81,144.74,144.71,144.37,142.70,142.67,142.62,142.54,
142.44,142.40,142.31,142.21,142.19,141.95,141.75,141.71,141.43,141.37,141.27,
141.24,141.13,140.89,139.74,139.63,139.56,139.25,139.07,137.61,137.33,135.92,
131.32(3C),126.16,113.93(3C),86.54(sp3-Cof C60),78.38(sp3-C of C60),55.27,
42.25；FT-IRν/cm-1(KBr),2948,2829,1707,1603,1464,1432,1360,1255,1170,1052,1031,
840,767,573,526；UV-vis(CHCl3)λmax/nm 260,318,420,689；MALDI-TOF MS m/z calcd
for C69H11NO3Na[M+Na]+924.0632,found 924.0629。
Embodiment above describes the general principle of the present invention, main features and advantages, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, the original for simply illustrating the present invention described in above-described embodiment and specification
Reason, under the scope for not departing from the principle of the invention, various changes and modifications of the present invention are possible, and these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (3)
- A kind of 1. FeCl2·4H2[60] rich synthetic method for strangling alkene oxazole derivative and [60] fowler 01 derivatives that O promotes, its It is characterised by that detailed process is：Using [60] fullerene and Weinreb acid amides as reaction raw materials, using internal oxidition strategy, pass through FeCl2·4H2Relay cascade reaction synthesis [60] Fu Le alkene oxazole derivative occurs for O facilitation and [60] Fullerol derives Thing；The synthetic route of [60] the Fu Le alkene oxazole derivatives is：Wherein R1For methoxyl group, to oxygen benzyl, acetyl group, benzoyl or ester group, R2For H or phenyl, R3For methyl, to methoxy Base, adjacent chlorine, m-chloro or to acetyl group.The synthetic route of [60] the fowler 01 derivatives is：Wherein R is to methoxyl group, adjacent methyl, to methyl, ester group, adjacent chlorine, m-chloro or H.
- 2. FeCl according to claim 12·4H2[60] Fu Le alkene oxazole derivative and [60] Fullerol that O promotes derive The synthetic method of thing, it is characterised in that the specific synthesis step of [60] the Fu Le alkene oxazole derivatives is：It is first that [60] are rich Strangle alkene, FeCl2·4H2O and N- methoxy benzamide derivatives are added in dry reaction tube, add o-dichlorohenzene simultaneously Ultrasound is completely dissolved [60] fowler, and then cock beyond the Great Wall is placed in stirring reaction in 80-110 DEG C of oil bath pan, after reaction terminates Salt and other insoluble matters first are filtered out with short column, decompression rotation removes solvent, with GF254 silica gel wet method dress posts, first uses carbon disulfide Elute pillar, then with carbon disulfide by the sample being spin-dried for all dissolving, loading, mistake post, first provide unreacted with carbon disulfide [60] fowler, then with CS2/ DCM mixed liquors are that eluant, eluent carries out affording target product [60] Fu Le alkene oxazole derivatives, Described N- methoxy benzamide derivatives are
- 3. FeCl according to claim 12·4H2[60] Fu Le alkene oxazole derivative and [60] Fullerol that O promotes derive The synthetic method of thing, it is characterised in that the specific synthesis step of [60] the fowler 01 derivatives is：First by [60] fullerene, FeCl2·4H2O and N- methyl-N-methoxy heterocyclic carbamate derivatives are added in dry reaction tube, add o-dichlorohenzene And ultrasound is completely dissolved [60] fullerene, then cock beyond the Great Wall is placed in stirring reaction in 90-110 DEG C of oil bath pan, reaction knot Shu Houxian filters out salt and other insoluble matters with short column, adds triethylamine during filtering, then again with toluene elution pillar, finally Decompression rotation remove solvent, with GF254 silica gel wet method dress posts, first with carbon disulfide elution pillar, will be then spin-dried for carbon disulfide The whole dissolvings of sample, loading, post is crossed, first provide unreacted [60] fullerene with carbon disulfide, then with CS2/ DCM mixed liquors are made Carry out affording target product [60] fowler 01 derivatives for eluant, eluent, the N- methyl-N-methoxies benzamide derives Thing is
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| CN108863735A (en) * | 2018-07-17 | 2018-11-23 | 河南师范大学 | The synthetic method of one kind [60] fullerene and cyclopentanone and [60] fullerene and 2- cyclohexenone compounds |
| CN110343064A (en) * | 2019-07-31 | 2019-10-18 | 河南师范大学 | The synthetic method of one kind [60] fullerene and tetrahydro cyclopentyl [2,3-b] indole derivatives |
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| CN110343064A (en) * | 2019-07-31 | 2019-10-18 | 河南师范大学 | The synthetic method of one kind [60] fullerene and tetrahydro cyclopentyl [2,3-b] indole derivatives |
| CN110343064B (en) * | 2019-07-31 | 2022-10-25 | 河南师范大学 | Synthesis method of [60] fullerene-tetrahydrocyclopenta [2,3-b ] indole derivative |
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