CN103923032A - Synthesis method of polysubstituted oxazole and polysubstituted imidazole - Google Patents

Synthesis method of polysubstituted oxazole and polysubstituted imidazole Download PDF

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CN103923032A
CN103923032A CN201410183341.7A CN201410183341A CN103923032A CN 103923032 A CN103923032 A CN 103923032A CN 201410183341 A CN201410183341 A CN 201410183341A CN 103923032 A CN103923032 A CN 103923032A
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diketone
polysubstituted
ethyl acetate
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CN103923032B (en
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景崤壁
陆海龙
王磊
谭晓东
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Yangzhou 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
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention discloses a synthesis method of polysubstituted oxazole and polysubstituted imidazole, and relates to the technical field of chemical synthesis of two compounds. The synthesis method comprises the following steps: firstly, mixing and stirring o-dione, ammonium acetate and acetic acid, then heating to 95-105DEG C, reacting for 170-190 minutes, adding water after the reaction is over, regulating the pH value of the system to be 7 through saturated sodium bicarbonate, extracting the mixture with ethyl acetate, then evaporating to remove a solvent, and performing column chromatography on residues to simultaneously obtain tri-substituted oxazole and tri-substituted imidazole. The polysubstituted oxazole and polysubstituted imidazole can be simultaneously synthesized through one-step reaction, compared with the similar multi-step methods, the steps of the method are shortened, the technological process is simple to operate, and expensive or high-pollution substances are ot needed to be adopted as catalysts. The prepared products are higher in purity, and fewer in side products.

Description

The synthetic method of Duo substituted oxazole and polysubstituted imidazoles
Technical field
The present invention relates to the chemosynthesis technical field of two compounds.
Background technology
Substituted oxazole is many because its good physiologically active enjoys scientist to pay close attention to the synthetic method of substituted oxazole, as: bitter almond oil camphor can react generation substituted oxazole Huo person oxazole with nitrile or methane amide and under aluminum chloride and triflic acid catalyzes, react synthetic substituted oxazole with halides under effect of sulfuric acid, all these methods are used strongly-acid material to make catalyzer conventionally, replace second diketone and there is not yet bibliographical information in the method for next step synthetic 2,4,5-tri-substituted oxazole of acetic acid effect.
The synthetic method of substituted imidazole is also many, wherein generates with replacing second diketone and aldehyde reaction, and the method for 2,4,5-tri-substituted imidazole is mainly confined to take special catalyzer, as: HClO 4/ SiO 2, H 2sO 4/ SiO 2, BF 3/ SiO 2, NaHSO 4/ SiO 2or zeolite etc., these catalyzer or acid and corrodibility is stronger, or expensive, simple taking at present replaces the method that second diketone reacts generation 2,4,5-tri-substituted imidazole under acetic acid catalysis and there is not yet bibliographical information.
Summary of the invention
The present invention seeks to propose the preparation method of the simple Duo substituted oxazole of a kind of technique and polysubstituted imidazoles.
The present invention first will be warmed up to 95～105 DEG C of reaction 170～190min after adjacent diketone, ammonium acetate and acetic acid mix and blend, after finishing, reaction adds water, and adjust the pH value to 7 of system with saturated sodium bicarbonate aqueous solution, mixture is extracted with ethyl acetate rear steaming and desolventizes, and residue obtains San substituted oxazole and tri-substituted imidazole after column chromatography simultaneously.
Above-mentioned reaction times and temperature are all comparatively suitable reaction times of this reaction and temperature, and excess Temperature reaction by-product rate is too high, and the too low reaction of temperature can not be carried out, and time shorten can cause reaction not exclusively, and time lengthening causes by-product rate too much.The pH value of wherein adjusting system with saturated sodium bicarbonate aqueous solution, as too low in pH value, product salify is and water-soluble, and product can not be extracted out, as too high in pH value, causes the waste of sodium bicarbonate.
The present invention can synthesize Duo substituted oxazole and polysubstituted imidazoles by single step reaction simultaneously, and the method is compared with similar multistep processes, and obviously step shortens, and technological process of the present invention is simple to operate simultaneously, does not adopt expensive or pollutes larger material and make catalyzer.The product purity that the present invention makes is higher, and by product is less.
The molar ratio of described adjacent diketone, ammonium acetate and acetic acid is 1 ︰ 25 ︰ 250, and under this ratio, the productive rate of product is the highest, and by product is minimum.
The mass ratio of the described water adding and acetic acid is 1 ︰ 10, solvent waste when hypervolia extracts, and the water yield is crossed while extraction at least percentage extraction compared with low and cause waste.
The solvent of described extraction is ethyl acetate, and the lower while effect of extracting of this solvent price is best.
Column chromatography adopts silica gel solid phasing, and eluent is the mixture of ethyl acetate and hexanaphthene, and the mixed volume ratio of described ethyl acetate and hexanaphthene is 1 ︰ 4.Ethyl acetate and hexanaphthene polarity moderate and to environmental facies to close friend, good separating-purifying product under this proportioning.
It is adjacent diketone that the synthetic method of Duo substituted oxazole of the present invention and polysubstituted imidazoles can specifically adopt the one in bromophenyl second diketone between benzil, di-p-tolyl second diketone, two rubigan second diketone, the two pairs of bromophenyl second diketone or two.Adopt different materials, can obtain respectively different concrete substituted oxazoles, polysubstituted imidazoles.
Embodiment
Example 1: preparation 2,4,5-tri-Ben oxazole and 2,4,5-triphen imidazoles:
In 50ml round-bottomed flask, add successively 1mmol benzil, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4,5-tri-Ben oxazole, white solid, fusing point: 113 ~ 115 DEG C, productive rate: 23%.
1H NMR(600 MHz, DCCl 3) δ(ppm): 8.177（s, 1H, ArH), 8.166(s, 1H, ArH), 7.745 (s, 1H, ArH), 7.733 (s, 1H, ArH), 7.697 (s, 1H, ArH), 7.684（s, 1H, ArH), 7.457-7.507 (m, 3H, ArH), 7.354-7.431 (m, 6H, ArH);
13C NMR (600 MHz, CDCl 3) δ(ppm): 159.40, 145.20, 136.08, 131.91, 130.75, 129.11, 128.98, 128.92, 128.66, 128.39, 128.12, 127.64, 126.57, 126.42, 126.07。
. 2,4,5-triphen imidazoles, white solid, fusing point: 270 ~ 271 DEG C, productive rate: 63%.
1H NMR(600 MHz, DMSO- d 6) δ(ppm): 12.702 (s, 1H, NH), 8.091 (s, 1H, ArH), 8.078 (s, 1H, ArH), 7.557 (s, 1H, ArH), 7.544 (s, 1H, ArH), 7.436-7.514 (s, 6H, ArH), 7.367-7.391 (s, 2H, ArH), 7.293-7.318 (s, 2H, ArH), 7.212-7.236 (s, 1H, ArH);
13C NMR (600 MHz, DMSO- d 6) δ(ppm): 145.471 137.110 135.189 131.092 130.353 128.626 128.605 128.436 128.210 128.192 128.131 127.727 127.044 126.463 125.174。
Example 2: preparation 2,4,5-, tri-Dui Jia oxygen Ben Ji oxazoles and 2,4,5-, tri-p-methoxyphenyl imidazoles:
In 50ml round-bottomed flask, add successively 1mmol bis-p-methoxyphenyl second diketone, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4,5-tri-Dui Jia oxygen Ben Ji oxazoles, fusing point: 138 ~ 139 DEG C of white solids, productive rate: 22%.
1c 1H NMR(600 MHz, CDCl 3) δ(ppm): 8.084 (s, 1H, ArH), 8.069 (s, 1H, ArH), 7.643 (s, 1H, ArH), 7.629 (s, 1H, ArH), 7.589 (s, 1H, ArH), 7.575 (s, 1H, ArH), 6.993 (s, 1H, ArH), 6.979 (s, 1H, ArH), 6.906-6.935 (s, 4H, ArH), 3.875 (s, 3H, OCH 3), 3.846 (s, 6H, OCH 3);
13C NMR (600 MHz, CDCl 3) δ(ppm): 161.23, 159.68, 159.59, 144.42, 135.13, 129.31, 128.01, 127.93, 125.32, 121.94, 120.40, 114.16, 114.13, 114.03, 55.38, 55.33, 55.30。
2,4,5-, tri-p-methoxyphenyl imidazoles, white solid, fusing point: 184 ~ 185 DEG C, productive rate: 61%.
2c 1H NMR(600 MHz, DMSO- d 6) δ(ppm): 12.469 (s, 1H, NH), 7.997 (s, 1H, ArH), 7.983 (s, 1H, ArH), 7.422-7.436 (s, 4H, ArH), 7.040 (s,1H,ArH), 7.026 (s,1H, ArH), 6.932-6.946 (s, 4H, ArH), 3.812 (s, 3H, OCH 3), 3.773 (s, 6H, OCH 3);
13C NMR (400 MHz, DMSO- d 6) δ(ppm):159.122 157,801 144.796 143.281 135.907 129.505 129.440 129.404 129.343 128.105 128.043 127.998 127.963 127.905 126.413 126.363 126.323 126.288 123.243 123.104 113.933 55.104 55.061 54.995。
Example 3: preparation 2,4,5-, tri-Dui Lv Ben Ji oxazoles and 2,4,5-, tri-rubigan imidazoles:
In 50ml round-bottomed flask, add successively 1mmol bis-rubigan second diketone, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4,5-tri-Dui Lv Ben Ji oxazoles, fusing point: 155 ~ 156 DEG C, white solid, productive rate: 33%.
1H NMR(600 MHz, CDCl 3) δ(ppm): 8.068 (s, 1H, ArH), 8.054 (s, 1H, ArH), 7.635 (s, 1H, ArH), 7.622 (s, 1H, ArH), 7.579 (s, 1H, ArH), 7.565 (s, 1H, ArH), 7.473 (s, 1H, ArH), 7.459 (s, 1H, ArH), 7.394 (s, 1H, ArH), 7.386 (s, 1H, ArH), 7.380 (s, 1H, ArH),7.372 (s, 1H, ArH);
13C NMR (600 MHz, CDCl 3) δ(ppm):159.58, 147.33, 144.96, 136.82, 136.26, 136.21, 135.31, 134.86, 134.44, 131.08, 130.55, 129.33, 129.21, 129.19, 129.03, 128.99, 128.78, 127.87, 127.76, 126.99, 125.52。
2,4,5-, tri-rubigan imidazoles white solids, fusing point: 276 ~ 277 DEG C, productive rate: 53%.
1H NMR(400 MHz, DMSO- d 6) δ(ppm): 12.873 (s, 1H, NH), 8.093 (s, 1H, ArH), 8.072 (s, 1H, ArH), 7.515-7.564 (s, 10H, ArH);
13C NMR (400 MHz, DMSO- d 6) δ(ppm):145.350 133.435 129.330 129.236 129.176 129.162 129.137 129.116 129.099 129.084 129.058 129.032 128.990 128.966 128.947 128.910 128.891 128.870 128.830 128.802 127.360。
Example 4: preparation 2,4,5-, tri-Dui Xiu Ben Ji oxazoles and 2,4,5-tri-are to bromophenyl imidazoles:
In 50ml round-bottomed flask, add successively 1mmol bis-to bromophenyl second diketone, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4,5-tri-Dui Xiu Ben Ji oxazoles, fusing point: 198 ~ 199 DEG C of white solids, productive rate: 55%.
1H NMR(600 MHz, CDCl 3) δ(ppm): 8.012 (s, 1H, ArH), 7.998 (s, 1H, ArH), 7.642 (s, 1H, ArH), 7.628 (s, 1H, ArH), 7.504-7.581 (s, 8H, ArH);
13C NMR (600 MHz, CDCl 3) δ(ppm): 159.702 145.045 136.352 132.164 132.141 131.986 130.994 129.591 128.079 127.939 127.407 125.921 125.229 123.101 122.673。
2,4,5-tri-is to bromophenyl imidazoles white solid, fusing point: 282 ~ 283 DEG C, and productive rate: 22%.
1H NMR(600 MHz, DMSO- d 6) δ(ppm): 12.878 (s, 1H, NH), 8.021(s, 1H, ArH), 8.002(s, 1H, ArH), 7.652-7.702(s, 4H, ArH), 7.536(s, 1H, ArH), 7.516(s, 1H, ArH), 7,436-7.482(s, 4H, ArH);
13C NMR (400 MHz, DMSO- d 6) δ(ppm):157.411 156.839 155.666 150.035 144.940 142.163 141.610 138.774 133.844 131.658 131.634 131.222 130.246 129.617 129.123 128.996 128.180 127.683 127.446 127.103 121.591。
Example 5: preparation tri-Xiu Ben Ji oxazoles of 2,4,5-and tri-bromophenyl imidazoles of 2,4,5-:
In 50ml round-bottomed flask, add successively bis-bromophenyl second diketone of 1mmol, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4, tri-Xiu Ben Ji oxazoles of 5-, 138 ~ 139 DEG C of white solids, productive rate: 50%.
H NMR(600 MHz, CDCl 3) δ(ppm): 8.295 (s, 1H, ArH), 8.070-8.083 (s, 1H, ArH), 7.908 (s, 1H, ArH), 7.840 (s, 1H, ArH), 7.592-7.627 (s, 2H, ArH), 7.548-7.561 (s, 1H, ArH), 7.513-7.526(s,2H,ArH),7.364-7.391(s,1H,ArH), 7.275-7.281 (s, 2H, ArH)。
13C NMR (600 MHz, CDCl 3) δ(ppm): 159.223 144.953 136.356 133.715 132.077 131.728 131.070 130.460 130.373 130.240 130.191 129.467 129.450 128.712 126.495 125.142 125.093 123.022 122.999 122.941。
Tri-bromophenyl imidazoles white solids of 2,4,5-, 257 ~ 258 DEG C of productive rates 24%.
H NMR(600 MHz, DMSO- d 6) δ(ppm): 12,970 (s, 1H, NH), 8.284 (s, 1H, ArH), 8.084-8.096 (s, 1H, ArH), 7.761 (s, 2H, ArH), 7.603 (s, 1H, ArH), 7.590 (s,1H, ArH), 7.449-7.489 (s,4H, ArH), 7.408 (s, 1H, ArH), 7.293 (s, 1H, ArH)
13C NMR (600 MHz, DMSO- d 6) δ(ppm): 159.498 144.567 136.902 136.387 132.559 132.074 131.156 130.963 130.860 130.801 130.699 130.472 129.582 127.810 127.646 127.393 125.900 124.250 122.136 121.959 121.713。
Example 6: preparation 2,4,5-, tri-Dui Jia Ben Ji oxazoles and 2,4,5-, tri-p-methylphenyl imidazoles:
In 50ml round-bottomed flask, add successively 1mmol di-p-tolyl second diketone, 25mmol ammonium acetate and 15ml acetic acid. be heated to 100 DEG C of reaction 180min, 150ml water will be poured in system, neutralize pH value with saturated sodium bicarbonate aqueous solution and reach 7,20ml ethyl acetate extraction 3 times for system, combined ethyl acetate layer final vacuum is spin-dried for, and resistates is analysed (eluent is the mixing solutions that ethyl acetate and hexanaphthene volume ratio are 1:4) separated product with silica gel column chromatography thin layer.
Product Identification 2,4,5-tri-Dui Jia Ben Ji oxazoles, fusing point: 141 ~ 142 DEG C of white solids, productive rate: 25%.
1H NMR(600 MHz, CDCl 3) δ(ppm): 8.042 (s, 1H, ArH), 8.0266 (s, 1H, ArH), 7.615 (s, 1H, ArH), 7.601 (s, 1H, ArH), 7.568 (s, 1H, ArH), 7.555 (s, 1H, ArH), 7.284 (s, 1H, ArH), 7.271 (s, 1H, ArH), 7.256 (s, 1H, ArH), 7.206(s, 1H, ArH), 7.193 (s, 1H, ArH), 7.179 (s, 1H, ArH), 2.416 (s, 3H, CH 3), 2.387 (s, 3H, CH 3), 2.383 (s, 3H, CH 3);
13C NMR (600 MHz, CDCl 3) δ(ppm):161.11, 146.22, 141.50, 139.42, 138.89, 137.23, 130.95, 130.49, 130.39, 130.30, 129.05, 127.56, 127.51, 1272，
2,4,5-, tri-p-methylphenyl imidazoles, fusing point: 242 ~ 243 DEG C of white solids, productive rate 51%.
1H NMR(600 MHz, DMSO- d 6) δ(ppm):12.474 (s, 1H, NH), 7.962 (s, 1H, ArH), 7.949 (s, 1H, ArH), 7.397 (s, 4H, ArH), 7.278 (s, 1H, ArH), 7.265 (s, 1H, ArH), 7.147-7.179 (s, 4H, ArH)，2.347 ( s, 3H, CH 3), 2.318 (s, 6H, CH 3)。
13C NMR (400 MHz, DMSO- d 6) δ(ppm):167.353 159.668 145.206 137.414 129.090 128.820 128.707 128.602 127.644 127.564 127.536 127.493 127.439 127.414 127.388 127.339 127.319 127.270 127.103 126.799 125.002 20.795 20.720 20.698。
reaction expression of the present invention is:
Wherein Ar be phenyl, p-methylphenyl, p-methoxyphenyl, rubigan, to bromophenyl or a bromophenyl.

Claims (6)

1. the synthetic method of Duo substituted oxazole and polysubstituted imidazoles, it is characterized in that: first react be warmed up to 95～105 DEG C after adjacent diketone, ammonium acetate and acetic acid mix and blend to 170～190min, after finishing, reaction adds water, and adjust the pH value to 7 of system with saturated sodium bicarbonate aqueous solution, mixture steams and desolventizes after extraction, and residue obtains San substituted oxazole and tri-substituted imidazole after column chromatography simultaneously.
2. production method according to claim 1, is characterized in that: the molar ratio of described adjacent diketone, ammonium acetate and acetic acid is 1 ︰ 25 ︰ 250.
3. production method according to claim 1, is characterized in that: described in the water that adds and the mass ratio of acetic acid be 1 ︰ 10.
4. production method according to claim 1, is characterized in that: be ethyl acetate for the solvent extracting.
5. production method according to claim 1, is characterized in that: column chromatography adopts silica gel solid phasing, and eluent is the mixture of ethyl acetate and hexanaphthene, and the mixed volume ratio of described ethyl acetate and hexanaphthene is 1 ︰ 4.
6. according to production method described in claim 1 or 2 or 3 or 4 or 5, it is characterized in that: described adjacent diketone is the one in benzil, di-p-tolyl second diketone, two rubigan second diketone, two pairs of bromophenyl second diketone or two bromophenyl second diketone.
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CN104529903A (en) * 2015-01-14 2015-04-22 扬州大学 Method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole
CN104529809A (en) * 2014-10-10 2015-04-22 浙江大学 Preparation method polysubstituted imidazole derivatives
CN115536605A (en) * 2022-08-22 2022-12-30 广东工业大学 Preparation method and application of polysubstituted oxazole compound participated by boron reagent

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104529809A (en) * 2014-10-10 2015-04-22 浙江大学 Preparation method polysubstituted imidazole derivatives
CN104529903A (en) * 2015-01-14 2015-04-22 扬州大学 Method for synthesizing 2-methyl-4,5-diphenylimidazole and 2,3,4-triphenyl-oxazole
CN104529903B (en) * 2015-01-14 2017-06-09 扬州大学 The diphenyl-imidazole of 2 methyl 4,5 and 2, the synthetic method of 4,5 triphenyl-oxazoles
CN115536605A (en) * 2022-08-22 2022-12-30 广东工业大学 Preparation method and application of polysubstituted oxazole compound participated by boron reagent
CN115536605B (en) * 2022-08-22 2023-12-15 广东工业大学 Preparation method and application of polysubstituted oxazole compound with participation of boron reagent

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