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A kind of synthetic method of multi-substituted furyl derivatives
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A synthesis method and furan-based technology are applied in the field of synthesis of polysubstituted furan derivatives, can solve the problem of high raw material cost, and achieve the effects of high raw material utilization rate, pollution avoidance and low cost
Active Publication Date: 2019-11-05
上海菲越医药科技有限公司
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[0040] Aiming at the disadvantages of high raw material cost, low yield, heavy metal or precious metal as catalyst in the existing furan ring construction method, another object of the present invention is to provide a method using cheap propiophenones and dimethyl A method for synthesizing furyl-o-diketone derivatives with high yield in one pot under mild conditions and without the catalysis of heavy gold or precious metals using sulfoxide as a raw material. The furyl-o-diketone derivatives constructed by this method have a novel furyl The parent structure of o-diketone, and it also contains multiple aryl groups, alkyl sulfides and other modifiable groups, providing a new intermediate structure for drug synthesis
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Embodiment 1
[0136] Reaction of propiophenone with DMSO (7a)
[0137]
[0138]77.9 mg of a yellow solid was obtained with a yield of 89%.
[0139] Characterization data: 1H NMR (400MHz, CDCl3): δ8.17(d, J=7.6Hz, 1H), 8.05(d, J=7.7Hz, 1H), 7.70(t, J=7.3Hz, 1H), 7.63 –7.52(m,2H),7.48(t,J=7.5Hz,1H),7.44(s,1H),2.51(s,2H).13C NMR(100MHz,CDCl3):δ190.6,181.6,180.6,149.2, 148.2, 137.6, 135.6, 135.3, 133.2, 132.1, 130.3, 129.7, 129.1, 128.6, 119.8, 15.9. HRMS(EI) m / z calcd for C 20 h 14 o 4 S[M+]: 350.0613; found, 350.0617.
Embodiment 2
[0141] Reaction of 2-fluoropropiophenone with DMSO (7b)
[0142]
[0143] 61.6 mg of a yellow solid was obtained with a yield of 67%.
[0144] Characterization data: 1 H NMR (400MHz, CDCl 3 ):δ7.95(td,J=7.9,1.7Hz,1H),7.73–7.60(m,2H),7.53–7.47(m,1H),7.44(s,1H),7.35(t,J=7.6 Hz,1H),7.20(dt,J=10.0,8.1Hz,2H),7.09–7.01(m,1H),2.56(s,3H). 13 C NMR (100MHz, CDCl 3 ), 136.8, 133.9(d, J=8.7Hz), 130.9, 130.5(d, J=2.4Hz), 125.2(d, J=13.8Hz), 125.0(d, J=3.3Hz), 124.2(d, J= 3.6Hz), 121.6(d, J=11.0Hz), 119.0(s), 116.6(d, J=21.5Hz), 116.3(d, J=21.8Hz), 15.7. HRMS(EI) m / z calcd for C 20 h 12 f 2 o 4 S[M + ]: 386.0424; found, 386.0426.
Embodiment 3
[0146] Reaction of 3,4-difluoropropiophenone with DMSO (7c)
[0147]
[0148] 66.4 mg of a yellow solid was obtained with a yield of 63%.
[0149] Characterization data: 1 H NMR (400MHz, CDCl 3 ): δ8.07(t, J=9.2Hz, 1H), 7.98(t, J=8.8Hz, 1H), 7.91(d, J=4.4Hz, 1H), 7.48(s, 1H), 7.41–7.28 (m,2H),2.54(s,3H). 13 C NMR (100MHz, CDCl 3 ): δ187.20, 178.73, 178.61, 149.15, 147.79, 138.62, 132.43(dd, J=4.6, 3.3Hz), 129.16(dd, J=5.0, 3.5Hz), 128.07(dd, J=7.9, 3.7Hz), 127.03(dd, J=7.4, 3.7Hz), 120.35, 119.54(d, J=2.0Hz), 119.42–119.30(m), 119.14(d, J=1.6Hz), 118.28(d, J=18.1Hz) ,117.71(d,J=17.8Hz),15.89.HRMS(EI)m / z calcd for C 20 h 10 f 4 o 4 S[M + ]: 422.0236; found, 422.033.
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Abstract
The invention discloses a polysubstituted furan derivative synthesis method. A polysubstituted furan derivative comprises a furyl o-diketone matrix structure and a plurality of modifiable groups suchas aryl and a thioether group and is a novel drug intermediate. The synthesis method is characterized in that an ethyl phenyl ketone compound is subjected to cyclization reaction in a dimethyl sulfoxide solution system containing persulfate and iodine and / or bromine to obtain the polysubstituted furan derivative. Low-cost ethyl phenyl ketone and dimethyl sulfoxide serve as raw materials, reactionconditions are mild, synthesis is finished by a one-pot method without the catalytic action of heavy metals or precious metals, reaction yield is high, and industrial production is facilitated.
Description
technical field [0001] The present invention relates to a method for synthesizing multi-substituted furan derivatives, in particular to a method for constructing furan derivatives with furyl-o-diketone as the parent through propiophenone compounds and dimethyl sulfoxide, which belongs to the synthesis technology of pharmaceutical intermediates field. Background technique [0002] Oxygen heterocyclic compounds are an important part of organic compounds, and are important structural units in many natural products with biological activity ([1] Atul G, Amit K.Ashutosh, R.Synthesis, Stereochemistry, Structural Classification, and Chemical Reactivity of Natural Pterocarpans. Chem. Rev., 2013, 113, 1614-1640; [2] Gu Z, Zakarian A. Studies towards the Synthesis of Maoecrystal V. Org. Lett., 2011, 13: 1080-1082). Therefore, the synthesis of oxygen-containing heterocyclic compounds has always been a research hotspot in organic synthesis. Studies have found that oxygen-containing het...
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