CN104892539B - A kind of new synthetic method of 2 aryl benzoxazoles class compounds of iron catalysis - Google Patents

A kind of new synthetic method of 2 aryl benzoxazoles class compounds of iron catalysis Download PDF

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CN104892539B
CN104892539B CN201510289646.0A CN201510289646A CN104892539B CN 104892539 B CN104892539 B CN 104892539B CN 201510289646 A CN201510289646 A CN 201510289646A CN 104892539 B CN104892539 B CN 104892539B
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class compounds
synthetic method
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CN104892539A (en
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张松林
胡伟业
张方
郑松林
吴三
王茹
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Suzhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals

Abstract

The invention discloses a kind of new synthetic method of 2 aryl benzoxazoles class compounds of iron catalysis, it is in the presence of molysite, part and alkali, using benzamide and adjacent bromo-iodobenzene as raw material, 2 aryl benzoxazoles class compounds are directly obtained by C N couplings, C O couplings at a certain temperature.Biological metal iron is successfully incorporated into the synthesis of the aryl benzoxazoles class compound of drug matrices 2 by the present invention, avoids the use of the metals such as highly toxic palladium, and the use range of the method is extended among the substrate containing different substituents.The present invention also successfully develops a kind of catalyst system and catalyzing that can have catalytic effect to C N, C O coupling simultaneously, substantially increases security of the 2 aryl benzoxazoles in building-up process.

Description

A kind of new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis
Technical field
The present invention relates to chemical organic synthesis field, more particularly to a kind of 2- aryl benzoxazoles class compounds of iron catalysis New synthetic method.
Background technology
Heterocyclic compound is the fragment of many natural products and medicine, and the azole compounds of wherein 2- aryl substitution are known Some medicines main body, it all shows very high bioactivity in antitumor, antiviral substance, antibacterial material, There is very magical effect especially for the duchenne muscular dystrophy caused by positioned at the gene mutation of No. XP21 (J.Med.Chem.2011,54,3241-3250).Virtue is broadly divided into for the synthetic method of 2- aryl benzoxazoles class compounds The oxidative cyclization (Angew.Chem.Int.Ed.2008,47,9330-9333) of fragrant amine and the arylation of benzoxazoles class compound (Synthesis 2015,47,42-48) two kinds of approach.As the research to 2- aryl benzoxazoles class compounds is goed deep into, more The method of the such compound of synthesis be reported out, 2004, Frank Glorius et al. were with adjacent dihalo thing aromatic hydrocarbons and benzene Formamide and its derivative be raw material under the catalysis of CuI/DMEDA systems, in K2CO3In the presence of it is even by the step of C-N, C-O two Connection has obtained 2- aryl benzoxazoles (Adv.Synth.Catal.2004,346,1661-1664).2014, Lennart Bunch et al. azepines neighbour's dihalo aromatic hydrocarbons is raw material with benzamide and its derivative, and also azepine is synthesized under palladium catalytic system 2- aryl benzoxazoles class compounds (Adv.Synth.Catal.2014,356,1047-1055).Have as one kind on medicine The bioactive molecule of important function, the security of its synthetic method are particularly important.Therefore, we have developed a kind of iron to urge Change system synthesizes 2- aryl benzoxazoles class compounds.
The content of the invention
The purpose of this part is to summarize some aspects of embodiments of the invention and briefly introduce some preferably to implement Example.It may do a little simplified or be omitted to avoid making our department in this part and the description of the present application summary and denomination of invention Point, the purpose of specification digest and denomination of invention obscure, and this simplification or omit and cannot be used for limiting the scope of the present invention.
In view of asked present in the new synthetic method of the 2- aryl benzoxazoles class compounds of above-mentioned and/or existing iron catalysis Topic, it is proposed that the present invention.
It is therefore an object of the present invention to provide a kind of synthesis of the 2- aryl benzoxazoles class compounds of iron catalysis newly side Method.
In order to solve the above technical problems, the invention provides following technical scheme：A kind of 2- aryl benzo of iron catalysis is disliked The new synthetic method of azole compounds, its be in the presence of molysite, part and alkali, using benzamide and adjacent bromo-iodobenzene as raw material, At a certain temperature 2- aryl benzoxazoles class compounds are directly obtained by C-N couplings, C-O couplings.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：Including being 1 in molar ratio by the benzamide, adjacent bromo-iodobenzene, molysite, part, alkali：1-5：0.1-1：0.1-1： 2-8 is added in reaction vessel, using toluene as agent is held, is reacted with inert gas shielding, reacts 30-60h at 100 DEG C -150 DEG C, Room temperature is cooled to, is extracted with ethyl acetate, purification is dried and obtains product.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：Adjacent bromo-iodobenzene is replaced using the bromo- 4- chloroiodobenzones of 2- or the bromo- 4- fluorine iodobenzenes of 2-.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：Benzamide is replaced using 4- fluorobenzamides or 4- methoxy benzamides.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：The inert gas is nitrogen or argon gas.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：Described, the iron salt catalyst is FeSO4·7H2O、Fe2O3、Fe2(SO4)3、Fe(acac)3、FeCl3、FeCl2· 4H2O or Fe2(ON2)3·9H2One or more in O.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：The alkali is potassium tert-butoxide, NaOMe, K2CO3、CsCO3Or the one or more in NaOAc.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：The part is 1,10- woodss ferrosin, DMEDA, TMEDA, dipyridyl or L-proline.
A kind of preferred side as the new synthetic method of the 2- aryl benzoxazoles class compounds of iron of the present invention catalysis Case, wherein：48h is reacted under the conditions of 110 DEG C.
The invention provides the new synthetic method of 2- aryl benzoxazoles class compound in one.Successfully by biological metal iron It is incorporated into the synthesis of drug matrices 2- aryl benzoxazoles class compounds, avoids the use of the metals such as highly toxic palladium, and The use range of the method is extended among the substrate containing different substituents.The present invention also successfully develops one kind can be same When have the catalyst system and catalyzing of catalytic effect to C-N, C-O coupling, substantially increase 2- aryl benzoxazoles in building-up process Security.
Embodiment
In order to facilitate the understanding of the purposes, features and advantages of the present invention, below by embodiment It is described in detail.
Many details are elaborated in the following description to facilitate a thorough understanding of the present invention, still the present invention can be with It is different from other manner described here using other to implement, those skilled in the art can be without prejudice to intension of the present invention In the case of do similar popularization, therefore the present invention is not limited by following public specific embodiment.
Secondly, " one embodiment " or " embodiment " referred to herein refers to may be included at least one realization side of the present invention Special characteristic, structure or characteristic in formula." in one embodiment " that different places occur in this manual not refers both to Same embodiment, nor the single or selective embodiment mutually exclusive with other embodiment.
Embodiment 1
Benzamide (0.5mmol, 60.5mg), Fe are added in Schlenk pipes2O3(0.1mmol, 15.9mg) and K2CO3 (0.5mmol, 69mg), with nitrogen protect reaction system (substituting gas three times), with syringe by adjacent bromo-iodobenzene (0.625mmol, 176.1mg), DMEDA (0.1mmol, 8.8mg) and toluene (2mL) are added in reaction system, are heated to 110 DEG C, stirring reaction 48h.Room temperature is cooled to after completion of the reaction, is added 20mL water and is extracted with ethyl acetate three times, separates organic phase, anhydrous slufuric acid Sodium is dried, and is spin-dried for, column chromatography obtains product 2- phenyl benzoxazoles.Yield 87%.1HNMR(400MHz,CDCl3):δ=8.26- 8.24(m,2H),7.78-7.76(m,1H),7.58-7.55(m,1H),7.52-7.49(m,3H),7.36-7.33(m,2H)；13C NMR(100MHz,CDCl3):δ=162.98,150.71,142.06,131.46,128.85,127.57,127.12,125.05, 124.52,119.97,110.54；LC-MS:[M+H]+M/z=196.1.
Embodiment 2
Using the method in similar embodiment 1, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- chloroiodobenzones of 2-, obtains 6- Chloro- 2- phenyl benzoxazoles, yield 75%,1H NMR(400MHz,CDCl3):δ=8.23-8.21 (m, 2H), 7.67 (d, J= 8.48Hz,1H),7.59-7.50(m,4H),7.34-7.32(m,1H)；13C NMR(100MHz,CDCl3):δ=163.69, 150.91,140.88,131.79,130.67,128.96,127.64,126.70,125.27,120.45,111.23；LC-MS: [M+H]+M/z=230.0.
Embodiment 3
Using similar synthetic method, the bromo- 4- chloroiodobenzones of 2- in embodiment 2 are replaced with 4- chlorine neighbours diiodo-benzene, obtain 6- Chloro- 2- phenyl benzoxazoles, yield 62%.
Embodiment 4
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- methyl iodobenzenes of 2-, obtains 6- methyl -2- Phenyl benzoxazoles, yield 80%,1H NMR(400MHz,CDCl3):δ=8.24-8.22 (m, 2H), 7.64 (d, J= 8.08Hz, 1H), 7.51 (s, 3H), 7.37 (s, 1H), 7.16 (d, J=7.96Hz, 1H), 2.50 (s, 3H)；13C NMR (100MHz,CDCl3):δ=162.53,151.02,139.88,135.53,131.24,128.83,127.43,127.32, 125.77,119.31,110.73,21.78；LC-MS:[M+H]+M/z=210.1.
Embodiment 5
Using similar method, the benzamide in embodiment 1 is replaced with 4- fluorobenzamides, obtains 2- (4- fluorophenyls) Benzoxazoles, yield：58%.1H NMR(400MHz,CDCl3):δ=8.27-8.23 (m, 2H), 7.77-7.75 (m, 1H), 7.58-7.56 (m, 1H), 7.36-7.34 (m, 2H), 7.21 (t, J=8.64Hz, 2H)；13CNMR(100MHz,CDCl3):δ= 164.80(d,1JC-F=251Hz), 162.14,150.75,142.04,129.81 (d,3JC-F=8.82Hz), 159.12, 124.64,123.47,119.97,116.17(d,2JC-F=22.06Hz), 110.55；LC-MS:[M+H]+M/z=214.1.
Embodiment 6
Using similar method, to replace the adjacent bromo-iodobenzene in embodiment 1 with the bromo- 4- methyl iodobenzenes of 2-, with 4- fluorobenzene first Acid amides replaces the benzamide in embodiment 1, obtains 2- (4- fluorophenyls) -6- methylbenzoxazoles, yield：92%.1H NMR (400MHz,CDCl3):δ=8.21 (s, 2H), 7.61 (d, J=7.96Hz, 1H), 7.35 (s, 1H), 7.17 (q, J= 8.28Hz,3H),2.49(s,3H)；13C NMR(100MHz,CDCl3):δ=164.63 (d,1JC-F=250.9Hz), 161.64, 151.01,139.82,135.57,129.59(d,3JC-F=8.75Hz), 125.84,123.65,119.26,116.08 (d,2JC-F =22.02Hz), 110.69,21.75；LC-MS:[M+H]+M/z=228.1.
Embodiment 7
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- chloroiodobenzones of 2-, with 4- fluorobenzamides Instead of the benzamide in embodiment 1,2- (4- fluorophenyls) -6- chlorobenzene diozaioles, yield are obtained：85%.1H NMR (400MHz,CDCl3):δ=8.22 (t, J=5.56Hz, 2H), 7.65 (d, J=8.4Hz, 1H), 7.56 (s, 1H), 7.33 (d, J=8.16Hz, 1H), 7.21 (t, J=8.36Hz, 2H)；13C NMR(100MHz,CDCl3):δ=164.95 (d,1JC-F= 251.84Hz),162.80,150.91,140.83,130.71,129.90(d,3JC-F=8.92Hz), 125.36,123.04, 120.42,116.28(d,2JC-F=22.08Hz), 111.21；LC-MS:[M+H]+M/z=248.0.
Embodiment 8
Using similar method, benzamide in embodiment 1 is replaced with 4- methyl benzamides, obtains 2- (4- methylbenzenes Base) benzoxazoles, yield：70%.1H NMR(400MHz,CDCl3):δ=8.13 (d, J=8.2Hz, 2H), 7.76-7.74 (m, 1H),7.56-7.54(m,1H),7.35-7.30(m,4H),2.42(s,3H)；13C NMR(100MHz,CDCl3):δ= 163.23,150.63,142.13,141.98,129.58,127.53,124.80,124.41,124.34,119.78,110.43, 21.56；LC-MS:[M+H]+M/z=210.1.
Embodiment 9
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- chloroiodobenzones of 2-, with 4- toluyls Amine replaces benzamide in embodiment 1, obtains 2- (4- aminomethyl phenyls) -6- chlorobenzene diozaioles, yield：65%.1H NMR (400MHz,CDCl3):δ=8.09 (d, J=8.24Hz, 2H), 7.64 (d, J=8.48Hz, 1H), 7.55 (s, 1H), 7.32- 7.29(m,3H),2.43(s,3H)；13C NMR(100MHz,CDCl3):δ=163.92,150.81,142.39,140.94, 130.35,129.67,127.58.125.11,123.88,120.23,111.10,21.63；LC-MS:[M+H]+M/z= 244.1.
Embodiment 10
Using similar method, the bromo- 4- methyl iodobenzenes of 2- replace the adjacent bromo-iodobenzene in embodiment 1, with 4- toluyls Amine replaces benzamide in embodiment 1, obtains 2- (4- aminomethyl phenyls) -6- methylbenzoxazoles, yield：45%.1H NMR (400MHz,CDCl3):δ=8.11 (d, J=8.2Hz, 2H), 7.62 (d, J=8.08Hz, 1H), 7.36 (s, 1H), 7.31 (d, J=8.0Hz, 2H), 7.15 (d, J=8.08Hz, 1H), 2.49 (s, 3H), 2.42 (s, 3H)；13C NMR(100MHz,CDCl3): δ=162.79,150.95,141.74,139.95,135.26,129.57,127.40,125.65,124.56,119.14, 110.66,21.77,21.60；LC-MS:[M+H]+M/z=224.1.
Embodiment 11
Using similar method, 4- methoxy benzamides replace the benzamide in embodiment 1, obtain 2- (4- methoxies Base phenyl) benzoxazoles, yield：50%.1H NMR(400MHz,CDCl3):δ=8.19 (d, J=8.92Hz, 2H), 7.75- 7.72 (m, 1H), 7.56-7.53 (m, 1H), 7.35-7.30 (m, 2H), 7.01 (d, J=8.88Hz, 2H), 3.87 (s, 3H)；13C NMR(100MHz,CDCl3):δ=163.11,162.24,150.59,142.21,129.32,124.54,124.36,119.61, 119.55,114.28,110.33,55.39；LC-MS:[M+H]+M/z=226.1.
Embodiment 12
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- fluorine iodobenzenes of 2-, obtains the fluoro- 2- phenyl of 6- Benzoxazoles, yield：50%.1H NMR(400MHz,CDCl3):δ=8.31-8.28 (m, 2H), 7.77 (q, J=4.88Hz, 1H),7.61-7.59(m,3H),7.40-7.37(m,1H),7.21-7.15(m,1H),13C NMR(100MHz,CDCl3):δ= 163.68,160.66(d,1JC-F=242.62Hz), 150.70 (d,3JC-F=14.57Hz), 138.40,131.60,128.95, 127.47,126.88,120.24(d,3JC-F=10.05), 112.54 (d,2JC-F=24.49Hz), 98.67 (d,2JC-F= 28.03Hz)；LC-MS:[M+H]+M/z=214.1
Embodiment 13
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- fluorine iodobenzenes of 2-, with 4- fluorobenzamides Instead of the benzamide in embodiment 1,2- (4- fluorophenyls) -6- fluorine benzoxazoles, yield are obtained：35%.1H NMR (400MHz,CDCl3):δ=8.22-8.18 (m, 2H), 7.69-7.66 (m, 1H), 7.30-7.26 (m, 1H), 7.23-7.18 (m,2H),7.13-7.07(m,1H)；13C NMR(100MHz,CDCl3):δ=164.81 (d,1JC-F=251.48Hz), 162.80,160.63(d,1JC-F=242.81Hz), 150.67 (d,3JC-F=14.67Hz), 138.32,129.67 (d,3JC-F= 8.86Hz),123.18(d,3JC-F=3.17Hz), 120.19 (d,3JC-F=9.99Hz), 116.22 (d,2JC-F=22.11Hz), 112.60(d,2JC-F=24.51Hz), 98.65 (d,2JC-F=28.04Hz)；LC-MS:[M+H]+M/z=232.1.
Embodiment 14
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- fluorine iodobenzenes of 2-, with 4- toluyls Amine replaces benzamide in embodiment 1, obtains 2- (4- aminomethyl phenyls) -6- fluorine benzoxazoles, yield：50%.1H NMR (400MHz,CDCl3):δ=8.09 (d, J=8.2Hz, 2H), 7.67-7.64 (m, 1H), 7.36-7.26 (m, 3H), 7.11- 7.05(m,1H),2.42(s,3H)；13C NMR(100MHz,CDCl3):δ=163.94,160.50 (d,1JC-F= 242.19Hz),150.58(d,3JC-F=14.58Hz), 142.13,138.44,129.65,127.41,124.07,119.98 (d,3JC-F=9.98Hz), 112.34 (d,2JC-F=24.47Hz), 98.56 (d,2JC-F=27.99Hz), 21.60；LC-MS:[M +H]+M/z=228.1.
Embodiment 15
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- fluorine iodobenzenes of 2-, with 4- methoxybenzene first Acid amides replaces the benzamide in embodiment 1, obtains 2- (4- methoxyphenyls) -6- fluorine benzoxazoles, yield：54%.1H NMR(400MHz,CDCl3):δ=8.14-8.11 (m, 2H), 7.65-7.61 (m, 1H), 7.27-7.24 (m, 1H), 7.09- 6.98(m,3H),3.87(s,3H)；13C NMR(100MHz,CDCl3):δ=163.74,162.30,160.30 (d,1JC-F= 241.83Hz),150.52(d,3JC-F=14.62Hz), 138.52,129.17,119.68 (d,3JC-F=10.02Hz), 114.32,112.16(d,2JC-F=24.39Hz), 98.45 (d,2JC-F=28.04Hz), 55.37；LC-MS:[M+H]+M/z= 244.1.
Embodiment 16
Using similar method, the adjacent bromo-iodobenzene in embodiment 1 is replaced with the bromo- 4- chloroiodobenzones of 2-, with 4- methoxybenzene first Acid amides replaces the benzamide in embodiment 1, obtains 2- (4- methoxyphenyls) -6- chlorobenzene diozaioles, yield：35%.1H NMR(400MHz,CDCl3):δ=8.16 (d, J=8.92Hz, 2H), 7.62 (d, J=8.44Hz, 1H), 7.55 (s, 1H), 7.32-7.29(m,1H),7.03-7.01(m,2H),3.89(s,3H)；13C NMR(100MHz,CDCl3):δ=163.83, 162.53,150.83,141.08,130.06,129.44,125.05,120.01,119.18,114.41,111.02,55.45； LC-MS:[M+H]+M/z=260.0.
It should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to preferable The present invention is described in detail embodiment, it will be understood by those within the art that, can be to the technology of the present invention Scheme is modified or equivalent substitution, and without departing from the spirit and scope of technical solution of the present invention, it all should cover in this hair Among bright right.

Claims (6)

  1. A kind of 1. new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis, it is characterised in that：
    In molysite Fe2O3, part DMEDA and alkali K2CO3In the presence of, using benzamide and adjacent bromo-iodobenzene as raw material, with inert gas Protection reaction, it is coupled at a certain temperature by C-N, C-O couplings directly obtain 2- aryl benzoxazoles class compounds.
  2. 2. the new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis according to claim 1, its feature exist In：Including,
    It is 1 in molar ratio by the benzamide, adjacent bromo-iodobenzene, molysite, part, alkali：1-5：0.1-1：0.1-1：2-8 is added to In reaction vessel, using toluene as solvent, reacted with inert gas shielding, in 100 DEG C of -150 DEG C of reaction 30-60h, be cooled to room Temperature, it is extracted with ethyl acetate, dries purification and obtain product.
  3. 3. the new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis according to claim 1 or 2, its feature It is：Adjacent bromo-iodobenzene is replaced using the bromo- 4- chloroiodobenzones of 2- or the bromo- 4- fluorine iodobenzenes of 2-.
  4. 4. the new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis according to claim 1 or 2, its feature It is：Benzamide is replaced using 4- fluorobenzamides or 4- methoxy benzamides.
  5. 5. the new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis according to claim 1 or 2, its feature It is：The inert gas is nitrogen or argon gas.
  6. 6. the new synthetic method of the 2- aryl benzoxazoles class compounds of iron catalysis according to claim 1 or 2, its feature It is：48h is reacted under the conditions of 110 DEG C.
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