CN106188044A - A kind of synthetic method of 3 arylthio imidazos [1,5 a] the N heterocyclic compound of catalysis of iodine - Google Patents

A kind of synthetic method of 3 arylthio imidazos [1,5 a] the N heterocyclic compound of catalysis of iodine Download PDF

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CN106188044A
CN106188044A CN201610528248.4A CN201610528248A CN106188044A CN 106188044 A CN106188044 A CN 106188044A CN 201610528248 A CN201610528248 A CN 201610528248A CN 106188044 A CN106188044 A CN 106188044A
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heterocyclic compound
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CN106188044B (en
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吴松松
冯承涛
刘甜甜
李忠
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Anhui University of Science and Technology
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

The invention belongs to organic synthesis field, disclose 3 arylthio imidazos [1 of a kind of catalysis of iodine, 5 a] synthetic method of N heterocyclic compound, including: by imidazo [1,5 a] N heterocyclic compound, diaryl disulfide, catalyst, it is added sequentially in reaction tube the DMSO (DMSO) with 1 2mL dissolve, is heated to 100～120 DEG C, reacts 6 10h.Reaction terminate after cool down reactant liquor to room temperature, post processing obtains imidazo [1,5 a] the N heterocyclic compound of No. 3 position sulfations.The first of the present invention elaborates the synthetic method of sulfation imidazo [1,5 a] N heterocycle compound, has the participation without transition metal, and reaction condition is gentle, and substrate spectrum is wide, yield high.Gather around have wide practical use in pharmacy and fluorescent material field.

Description

A kind of synthesis of 3-arylthio imidazo [1,5-a] the N-heterocyclic compound of catalysis of iodine Method
Technical field
The invention belongs to organic chemical synthesis field, be specifically related to a kind of R1And R2Substituted imidazo [1,5-a] N-heterocycle Compound and R3Substituted diaryldisulfide is under the conditions of catalysis of iodine, and the generation sulfation reaction of regioselectivity, preparation is each Plant sulfenyl substituted imidazo [1,5-a] heterocyclic compound.
Background technology
Imidazoheterocycles compounds is that a class is worth in biological medicine, pesticide and optical material field extensive application Nitrogenous fused heterocyclic compound.And the substituted Imidazoheterocyclic compounds of sulfenyl is same in pharmaceutical synthesis field as drug matrices There is huge application potential.Thus in recent years, the research to its synthetic method the most increasingly receives publicity.2011, Zhou Etc. reporting with diphenyl disulfide as raw material, under conditions of Hydro-Giene (Water Science). is catalyzed, imidazo [1, the 2-a] pyrrole of synthesis sulfation Pyridine compounds.The substrate that this synthetic method is adapted to is all 1-aryl substituted imidazo [1,2-a] pyridine, and needs transition The participation [Tetrahedron, 2011,67:3690] of metal.2014, Zhang etc. developed a kind of cesium carbonate promote with miaow Azoles also [1,2-a] pyridine compounds and their and imidazo [1,2-a] the N-heterocyclic that diaryldisulfide is Material synthesis sulfation Compound.This synthetic method weak base of 2 times of single amounts instead of transition metal [RSC Adv., 2014,4:19891].2015, Hajra etc. are that raw material successfully synthesizes 1-benzene under the catalytic condition of iodine with 2-phenylimidazole also [1,2-a] pyridine and benzene sulfonyl hydrazide Base imidazo [1,2-a] pyridine compounds and their [Org.Biomol.Chem., 2015,13:3314].In the same year, Hiebel etc. finds A kind of method of imidazo [1,2-a] pyridine compounds and their meeting the synthesis sulfation that Green Chemistry requires.This synthesis side Method with 1-phenylimidazole also [1,2-a] pyridine and phenylmercaptan. as raw material, with iodine as catalyst, hydrogen peroxide is as oxidant with ring The PEG that border is friendly400For carrying out [Green Chem., 2015,17:937] under conditions of the gentleness of solvent.Above-mentioned synthetic method All it is not involved with the sulfuration of imidazo [1,5-a] heterocyclic compound, and the imidazo [1,2-a] of synthesized sulfation is miscellaneous Cycle compound substituent group on No. 1 position of its heterocycle is aryl mostly.These all limit current imidazo nitrogen heterocyclic ring chemical combination The synthesis process of thing sulfation.
Summary of the invention
The invention provides the synthetic method of a kind of sulfation imidazo [1,5-a] N-heterocycle compound, the method with Imidazo [1,5-a] N-heterocycle is initial feed, and diaryldisulfide is that sulfiding reagent is at the 3 of imidazo [1,5-a] N-heterocycle C-S key, the sulfation product of synthesis imidazo [1,5-a] N-heterocycle is formed on number position.This invention the first elaborates sulfation The synthetic method of imidazo [1,5-a] N-heterocycle compound, has the participation without transition metal, and reaction condition is gentle, substrate Scope is wide, yield high.
A kind of sulfation method of imidazo [1,5-a] the N-heterocyclic compound of catalysis of iodine, including: by imidazo [1,5- A] N-heterocyclic compound (II), diaryl disulfide (III), iodine, it is added sequentially in reaction tube with the two of 1-2mL Methyl Asia maple (DMSO) is dissolved, and is heated to 100～120 DEG C, reacts 6-10h.React cooling reactant liquor after terminating, to room temperature, to locate afterwards Reason obtains imidazo [1,5-a] the N-heterocyclic compound (I) of No. 3 position sulfations, and reaction equation is shown below:
In above formula: R1For hydrogen, methyl, ethyoxyl, nitro or halogen, wherein halogen is fluorine；R2For phenyl, tolyl, 1-how Base, 2-furyl or aliphatic group, wherein aliphatic group is n-pro-pyl；R3For methyl, methoxyl group or nitro.
Wherein, the catalyst used is iodine；Any oxidant of interpolation is proceeded without in air atmosphere；React molten Agent is dimethyl sulfoxide (DMSO)；Reaction temperature is 100-120 DEG C；Response time is 6-10h.
In above-mentioned reaction, the mol ratio of preferred raw material is: imidazo [1,5-a] N-heterocyclic compound (II): diaryl Disulfide (III): catalyst (I2)=1: 0.6-1: 0.1-0.2.Dimethyl sulfoxide (DMSO) is 1-2mL.After having reacted, can The last handling process selected includes: extraction, rotary evaporation, column chromatography chromatogram is purified the miaow of the corresponding sulfation of isolated Azoles also [1,5-a] N-heterocyclic compound.
Imidazo [1,5-a] N-heterocyclic compound used in above-mentioned synthetic method is the synthesis of existing method, two Aryl disulfide, iodine and DMSO (DMSO) use commercially available prod.
This synthetic method the first elaborates the synthetic method of sulfation imidazo [1,5-a] N-heterocycle compound, tool Having the participation without transition metal, reaction condition is gentle, and substrate spectrum is wide, yield high.Lead in pharmacy and fluorescent material Territory is gathered around and is had wide practical use.
Detailed description of the invention
Embodiment 1-12
Proportioning raw materials and reaction condition according to Tables 1 and 2 add imidazo [1,5-in the pressure reaction tube of 10mL heavy wall A] quinoline compound (II), diphenyl disulfide compound (III), catalyst and organic solvent, mixing and stirring, according to table 2 After reaction condition has reacted, extraction, (developing solvent is the mixture of ethyl acetate and petroleum ether to column chromatography for separation, both volumes Than being 1:4-8) purification obtains imidazo [1, the 5-a] quinoline compound (I) of corresponding sulfation, reactional equation such as following formula institute Show:
Table 1
Table 2
In table 2, I2For elemental iodine, DMSO is DMSO.
Structure confirmation data
The imidazo [1,5-a] of No. 3 position sulfations by embodiment 1～12 preparation] the structure detection number of quinoline compound According to being respectively as follows:
The nuclear-magnetism of 1-phenyl-3-thiophenyl imidazo [1,5-a] quinoline compound (I-1) prepared by embodiment 1 Resonance (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.70-7.65(m,3H),7.56-7.51(m,5H),7.37-7.33(m,1H), 7.26-7.15(m,6H),7.11-7.07(m,1H)。
13C-NMR(100MHz,CDCl3)δ143.1,138.0,136.6,134.2,133.0,132.4,129.7,129.6, 129.4,128.8,128.8,127.8,127.2,125.6,125.5,123.5,122.5,117.4,116.5。
The 7-methyl isophthalic acid prepared by embodiment 2-phenyl-3-thiophenyl imidazo [1,5-a] quinoline compound (I-2) Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.70-7.68(m,2H),7.54-7.52(m,4H),7.47-7.42(m,2H), 7.31-7.29 (m, 2H), 7.21 (t, J=7.6Hz, 2H), 7.15-7.11 (m, 2H), 7.07-7.04 (m, 1H), 2.41 (s, 3H)。
13C-NMR(100MHz,CDCl3)δ142.8,138.1,135.3,134.1,133.1,130.4,129.8,129.5, 128.9,128.8,128.7,128.7,127.1,125.6,125.5,123.4,122.3,117.2,116.4,20.8。
7-ethyoxyl-1-phenyl-3-thiophenyl imidazo [1,5-a] quinoline compound (I-prepared by embodiment 3 Nuclear magnetic resonance, NMR 3) (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3) δ 7.69-7.67 (m, 2H), 7.54-7.50 (m, 4H), 7.46 (d, J=9.3Hz, 1H),7.26-7.17(m,4H),7.11-7.07(m,3H),6.80(dd,J1=9.3Hz, J2=2.8Hz, 1H), 4.07 (q, J= 6.9Hz, 2H), 1.43 (t, J=7.0Hz, 3H).
13C-NMR(100MHz,CDCl3)δ156.2,142.5,138.1,133.8,132.9,129.7,129.6,128.8, 127.2,127.0,126.5,125.5,123.4,122.3,118.6,116.9,116.0,111.5,63.8,14.7。
The 7-'s fluoro-1-phenyl-3-thiophenyl imidazo [1,5-a] quinoline compound (I-4) prepared by embodiment 4 Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.68-7.66(m,2H),7.60-7.51(m,5H),7.33(dd,J1= 8.5Hz,J2=2.9Hz, 1H), 7.28-7.26 (m, 2H), 7.22-7.19 (m, 2H), 7.13-7.08 (m, 2H), 6.97-6.92 (m,1H)。
13C-NMR(100MHz,CDCl3)δ160.8,158.4,143.0,137.7,133.8,132.7,129.8,129.7, 129.0,128.8,127.4,127.3,125.7,123.3,122.6,122.6,119.1,119.1,117.9,115.4, 115.2,113.9,113.7。
7-nitro-1-phenyl-3-thiophenyl imidazo [1,5-a] quinoline compound (I-5) prepared by embodiment 5 Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ8.55-8.53(m,1H),8.07-8.02(m,1H),7.70-7.56(m,7H), 7.31-7.29(m,2H),7.25-7.14(m,4H)。
13C-NMR(100MHz,CDCl3)δ136.9,130.3,129.6,129.4,129.3,129.2,128.9,127.8, 126.1,126.1,124.1,124.0,122.4,122.3,122.2,121.9,119.1,118.1,117.9。
3-'s thiophenyl-1-p-methylphenyl imidazo [1,5-a] quinoline compound (I-6) prepared by embodiment 6 Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.66(dd,J1=7.8Hz, J2=1.5Hz, 1H), 7.62-7.52 (m, 4H), 7.38-7.32(m,3H),7.27-7.14(m,6H),7.11-7.09(m,1H),2.47(s,3H)。
13C-NMR(100MHz,CDCl3)143.3,139.6,138.1,134.1,132.5,130.1,129.6,129.5, 128.8,128.0,127.7,127.1,125.6,125.5,125.5,123.4,122.3,117.4,116.5,21.5。
1-(2-furyl)-3-thiophenyl imidazo [1,5-a] quinoline compound (I-7) prepared by embodiment 7 Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3) δ 7.71-7.66 (m, 2H), 7.55 (d, J=9.3Hz, 1H), 7.44-7.37 (m, 2H),7.25-7.18(m,6H),7.12-7.08(m,1H),6.95-6.94(m,1H),6.68-6.67(m,1H),6.67(dd, J1=3.3Hz, J2=1.8Hz, 1H).
13C-NMR(100MHz,CDCl3)δ144.3,143.4,137.6,134.5,133.0,132.2,128.8,128.6, 127.3,125.9,125.7,125.5,124.3,123.1,116.8,116.2,113.5,112.0。
The 1-that prepared by embodiment 8 (1-how base)-3-'s thiophenyl imidazo [1,5-a] quinoline compound (I-8) Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3) δ 8.08 (d, J=8.2Hz, 1H), 7.97 (d, J=8.3Hz, 1H), 7.77 (dd, J1=7.0Hz, J2=1.2Hz, 1H), 7.66-7.62 (m, 3H), 7.52-7.48 (m, 1H), 7.36-7.35 (m, 2H), 7.31- 7.29(m,2H),7.25(s,1H),7.24-7.20(m,3H),7.13-7.09(m,1H),7.01-6.93(m,2H)。
13C-NMR(100MHz,CDCl3)141.2,138.1,133.9,133.7,132.4,132.3,130.7,130.4, 129.0,128.8,128.7,128.5,128.2,127.3,127.2,126.5,125.5,125.4,125.4,125.3, 123.6,122.6,116.9,116.5。
The nuclear magnetic resonance, NMR of 3-thiophenyl-1-n-pro-pyl imidazo [1,5-a] quinoline compound prepared by embodiment 9 (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3) δ 8.09 (d, J=8.5Hz, 1H), 7.60 (dd, J1=7.7Hz, J2=1.4Hz, 1H),7.51-7.47(m,1H),7.39-7.33(m,2H),7.11-7.05(m,4H),7.01-6.97(m,2H),3.32(t,J =7.72Hz, 2H), 2.00-1.94 (m, 2H), 1.05 (t, J=7.36Hz, 3H).
13C-NMR(100MHz,CDCl3)δ143.9,137.4,133.1,132.1,127.9,127.8,127.7,127.2, 125.6,124.7,124.2,121.7,119.2,115.7,115.5,33.3,19.5,12.9。
1-phenyl-the 3-prepared by embodiment 10 is to Tolylsulfanvl imidazo [1,5-a] quinoline compound (I-10) Nuclear magnetic resonance, NMR (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.60-7.54(m,3H),7.46-7.41(m,5H),7.27-7.23(m,1H), 7.14-7.10 (m, 3H), 7.05 (d, J=9.4Hz, 1H), 6.93 (d, J=8.0Hz, 2H), 2.16 (s, 3H).
13C-NMR(100MHz,CDCl3)δ142.9,135.6,134.2,133.9,133.1,132.4,129.8,129.6, 129.0, 128.8,128.8,128.5,127.9,127.8,125.6,125.5,123.4,117.4,116.6,20.9。
1-phenyl-the 3-prepared by embodiment 11 is to methoxy thiophenyl imidazo [1,5-a] quinoline compound (I- Nuclear magnetic resonance, NMR 11) (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ7.66-7.62(m,3H),7.57-7.49(m,5H),7.34-7.30(m,3H), 7.21-7.18 (m, 1H), 7.13 (d, J=9.3Hz, 1H), 6.78-6.76 (m, 2H), 3.72 (s, 3H).
13C-NMR(100MHz,CDCl3)δ158.4,142.7,133.4,133.1,132.4,130.5,129.7,129.6, 129.0,128.8,128.1,127.7,125.6,125.5,124.4,123.2,117.3,116.6,114.5,55.3。
1-phenyl-3-ortho-nitrophenyl sulfenyl imidazo [1,5-a] quinoline compound (I-prepared by embodiment 12 Nuclear magnetic resonance, NMR 12) (1H NMR and13C NMR) detection data be:
1H-NMR(400MHz,CDCl3)δ8.13(dd,J1=8.1Hz, J2=0.9Hz, 1H), 7.63-7.61 (m, 3H), 7.54-7.41 (m, 5H), 7.31 (t, J=7.2Hz, 1H), 7.25-7.11 (m, 4H), 6.96 (d, J=8.1Hz, 1H).
13C-NMR(100MHz,CDCl3)δ144.0,143.0,138.0,134.3,132.5,131.6,131.3,128.8, 128.6,128.0,127.8,127.2,127.1,124.8,124.7,124.4,124.0,123.5,119.3,116.3, 114.8。

Claims (5)

1. the synthetic method of 3-arylthio imidazo [1, a 5-a] N-heterocyclic compound, it is characterised in that: by imidazo [1, 5-a] N-heterocyclic compound (II), diaryl disulfide (III), catalyst, it is added sequentially in reaction tube with 1-2mL's DMSO (DMSO) dissolves, and is heated to 100-120 DEG C, reacts 6-10h, and post processing obtains the imidazo of No. 3 position sulfations [1,5-a] N-heterocyclic compound (I)；
Shown in described imidazo [1,5-a] N-heterocyclic compound structure such as formula (II):
In formula (II): R1For hydrogen, methyl, ethyoxyl, nitro or halogen, wherein halogen is fluorine；R2For phenyl, tolyl, 1-how Base, 2-furyl or aliphatic group, wherein aliphatic group is n-pro-pyl；
Shown in described diaryl disulfide structure such as formula (III):
In formula (III): R3For methyl, methoxyl group or nitro.
Method the most according to claim 1, it is characterised in that described material molar ratio is: imidazo [1,5-a] N-is miscellaneous Cycle compound (II): diaryldisulfide (III): catalyst=1: 0.6-1: 0.1-0.2.
The synthetic method of 3-arylthio imidazo [1,5-a] N-heterocyclic compound the most according to claim 1, its feature exists In, described reaction temperature is preferably 110 DEG C, and the response time is preferably 8h.
The most according to claim 1, the method for the synthesis of 3-arylthio imidazo [1,5-a] N-heterocyclic compound, its feature exists In, described catalyst is iodine.
The synthetic method of 3-arylthio imidazo [1,5-a] N-heterocyclic compound the most according to claim 1, its feature exists In, described organic solvent is preferably DMSO (DMSO) 1.5mL.
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CN111303117A (en) * 2020-03-13 2020-06-19 常州工程职业技术学院 Preparation method of nitrogen heterocyclic ring substituted indole thioether compound

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CN108383817A (en) * 2018-05-07 2018-08-10 青岛科技大学 A kind of synthetic method of thiocoumarin
CN108383817B (en) * 2018-05-07 2021-11-09 青岛科技大学 Synthetic method of thiocoumarin
CN108530445A (en) * 2018-06-22 2018-09-14 安徽理工大学 A kind of synthetic method of 3- cyanoimidazoles simultaneously [1,5-a] quinoline compound
CN110857299A (en) * 2018-08-24 2020-03-03 安徽理工大学 Synthesis method of 3-thiocyanoimidazo [1,5-a ] quinoline compound
CN110857299B (en) * 2018-08-24 2022-03-11 安徽理工大学 Synthesis method of 3-thiocyanoimidazo [1,5-a ] quinoline compound
CN111303117A (en) * 2020-03-13 2020-06-19 常州工程职业技术学院 Preparation method of nitrogen heterocyclic ring substituted indole thioether compound

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