CN106188044B - A kind of synthetic method of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds of catalysis of iodine - Google Patents

A kind of synthetic method of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds of catalysis of iodine Download PDF

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CN106188044B
CN106188044B CN201610528248.4A CN201610528248A CN106188044B CN 106188044 B CN106188044 B CN 106188044B CN 201610528248 A CN201610528248 A CN 201610528248A CN 106188044 B CN106188044 B CN 106188044B
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CN106188044A (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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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D471/04—Ortho-condensed systems

Abstract

The invention belongs to organic synthesis field, a kind of synthetic method of 3 arylthio imidazos [1,5 a] N heterocyclic compounds of catalysis of iodine is disclosed, including：By imidazo [1,5 a] N heterocyclic compounds, diaryl disulfide, catalyst is added sequentially to be dissolved with the dimethyl sub-maple (DMSO) of 1 2mL in reaction tube, is heated to 100~120 DEG C, reacts 6 10h.Reaction solution is cooled down after reaction to room temperature, and post processing obtains imidazo [1,5 a] N heterocyclic compounds of No. 3 position sulfations.The features such as the first of the present invention elaborates the synthetic method of sulfation imidazo [1,5 a] N heterocycle compounds, has the participation without transition metal, and reaction condition is mild, and substrate spectrum is wide, high income.It gathers around and has wide practical use in pharmacy and fluorescent material field.

Description

A kind of synthesis of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds of catalysis of iodine Method
Technical field
The invention belongs to organic chemical synthesis fields, and in particular to a kind of R1And R2Substituted imidazo [1,5-a] N- heterocycles Compound and R3Under the conditions of catalysis of iodine, the generation sulfation reaction of regioselectivity is prepared each substituted diaryldisulfide Imidazo [1,5-a] heterocyclic compound of kind sulfenyl substitution.
Background technology
Imidazoheterocycles class compound is a kind of in biological medicine, pesticide and optical material field extensive application value Nitrogenous fused heterocyclic compound.And the Imidazoheterocyclic compounds of sulfenyl substitution are similary in pharmaceutical synthesis field as drug matrices There is huge application potential.Thus in recent years, increasingly attracted attention to the research of its synthetic method.2011, Zhou Etc. reporting using diphenyl disulfide as raw material, under conditions of cuprous iodide catalysis, imidazo [1,2-a] pyrrole of sulfation is synthesized Pyridine class compound.The substrate that the synthetic method is adapted to all is imidazo [1,2-a] pyridine of 1- aryl substitution, and needs transition Metal participation [Tetrahedron, 2011,67:3690].2014, Zhang etc. developed that a kind of cesium carbonate promotes with miaow Azoles simultaneously [1,2-a] pyridine compounds and their and diaryldisulfide be Material synthesis sulfation imidazo [1,2-a] N- heterocyclics Compound.The weak base that the synthetic method is singly measured with 2 times instead of transition metal [RSC Adv., 2014,4:19891].2015, With 2- phenylimidazoles, simultaneously [1,2-a] pyridine and benzene sulfonyl hydrazide successfully synthesize 1- benzene to Hajra etc. for raw material under the catalytic condition of iodine Base imidazo [1,2-a] pyridine compounds and their [Org.Biomol.Chem., 2015,13:3314].The discoveries such as the same year, Hiebel A kind of method of imidazo [1,2-a] pyridine compounds and their for the synthesis sulfation for meeting Green Chemistry requirement.The synthesis side Method is using 1- phenylimidazoles, simultaneously [1,2-a] pyridine and benzenethiol are raw material, are oxidant and ring by catalyst, hydrogen peroxide of iodine The PEG of border close friend400For solvent it is mild under conditions of carry out [Green Chem., 2015,17:937].Above-mentioned synthetic method The vulcanization of imidazo [1,5-a] heterocyclic compound is all not involved with, and the imidazo [1,2-a] of synthesized sulfation is miscellaneous Substituent group of the cycle compound on No. 1 position of its heterocycle is aryl mostly.These all limit current imidazo nitrogen heterocyclic ring chemical combination The synthesis process of object sulfation.
The content of the invention
The present invention provides a kind of synthetic method of sulfation imidazo [1,5-a] N- heterocycle compounds, this method with Imidazo [1,5-a] N- heterocycles are initial feed, and diaryldisulfide is sulfiding reagent the 3 of imidazo [1,5-a] N- heterocycles C-S keys are formed on number position, synthesize the sulfation product of imidazo [1,5-a] N- heterocycles.This invention the first elaborates sulfation The synthetic method of imidazo [1,5-a] N- heterocycle compounds, the participation with no transition metal, reaction condition is mild, substrate The features such as scope is wide, high income.
A kind of sulfation method of the imidazo of catalysis of iodine [1,5-a] N- heterocyclic compounds, including：By imidazo [1,5- A] N- heterocyclic compounds (II), diaryl disulfide (III), iodine, be added sequentially in reaction tube use 1-2mL two Methyl Asia maple (DMSO) is dissolved, and is heated to 100~120 DEG C, reacts 6-10h.Reaction solution is cooled down after reaction to room temperature, it is rear to locate Reason obtains imidazo [1,5-a] N- heterocyclic compounds (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- furyls or aliphatic group, wherein aliphatic group are n-propyl；R3For methyl, methoxyl group or nitro.
Wherein, used catalyst is iodine；Any oxidant of addition is proceeded without in air atmosphere；React molten Agent is dimethyl sulfoxide (DMSO) (DMSO)；Reaction temperature is 100-120 DEG C；Reaction time is 6-10h.
In above-mentioned reaction, the molar ratio of preferred raw material is：Imidazo [1,5-a] N- heterocyclic compounds (II)：Diaryl Disulfide (III): catalyst (I2)=1: 0.6-1: 0.1-0.2.Dimethyl sulfoxide (DMSO) (DMSO) is 1-2mL.It, can after the completion of reaction The last handling process of selection includes：Extraction, rotary evaporation, column chromatography chromatogram carry out purifies and separates and obtain the miaow of corresponding sulfation Azoles simultaneously [1,5-a] N- heterocyclic compounds.
What imidazo [1,5-a] N- heterocyclic compounds used in above-mentioned synthetic method synthesized for existing method, two Aryl disulfide, iodine and dimethyl sub-maple (DMSO) use commercial product.
This synthetic method the first elaborates the synthetic method of sulfation imidazo [1,5-a] N- heterocycle compounds, tool There is the participation without transition metal, the features such as reaction condition is mild, and substrate spectrum is wide, high income.It is led in pharmacy and fluorescent material Domain, which is gathered around, to have wide practical use.
Specific embodiment
Embodiment 1-12
Imidazo [1,5- is added in the pressure-resistant reaction tube of 10mL heavy walls according to the raw material proportioning and reaction condition of Tables 1 and 2 A] quinoline compound (II), diphenyl disulfide compound (III), catalyst and organic solvent, it is mixed evenly, according to table 2 After the completion of reaction condition reaction, extraction, (solvent is the mixture of ethyl acetate and petroleum ether to column chromatography for separation, the two volume Than for 1:4-8) purifying obtains imidazo [1,5-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 dimethyl sub-maple.
Structure confirmation data
By embodiment 1~12 prepare No. 3 position sulfations imidazo [1,5-a]] quinoline compound structure detection number According to respectively：
By the nuclear-magnetism for 1- phenyl -3- thiophenyls imidazo [1,5-a] quinoline compounds (I-1) that embodiment 1 is prepared 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-1s being prepared by embodiment 2-phenyl-3- thiophenyls imidazo [1,5-a] quinoline compound (I-2) Nuclear magnetic resonance (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- thiophenyls imidazo [1,5-a] quinoline compounds (I- being prepared by embodiment 3 3) nuclear magnetic resonance (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。
Fluoro- 1- phenyl -3- thiophenyls imidazo [1,5-a] quinoline compounds (I-4) of 7- being prepared by embodiment 4 Nuclear magnetic resonance (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- nitros -1- phenyl -3- thiophenyls imidazo [1,5-a] quinoline compound (I-5) being prepared by embodiment 5 Nuclear magnetic resonance (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- thiophenyl -1- p-methylphenyls imidazo [1,5-a] quinoline compounds (I-6) being prepared by embodiment 6 Nuclear magnetic resonance (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- furyls) -3- thiophenyls imidazo [1,5-a] quinoline compound (I-7) being prepared by embodiment 7 Nuclear magnetic resonance (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。
1- (1- how base) -3- thiophenyls imidazo [1,5-a] quinoline compound (I-8) being prepared by embodiment 8 Nuclear magnetic resonance (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。
By the nuclear magnetic resonance of 3- thiophenyls -1- n-propyls imidazo [1,5-a] quinoline compound that embodiment 9 is prepared (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。
By the 1- phenyl -3- that embodiment 10 is prepared to Tolylsulfanvl imidazo [1,5-a] quinoline compound (I-10) Nuclear magnetic resonance (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。
By the 1- phenyl -3- that embodiment 11 is prepared to methoxy thiophenyl imidazo [1,5-a] quinoline compound (I- 11) nuclear magnetic resonance (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 compounds (I- being prepared by embodiment 12 12) nuclear magnetic resonance (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 (3)

1. a kind of synthetic method of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds, it is characterised in that：By imidazo [1, 5-a] N- heterocyclic compounds (II), diaryl disulfide (III), catalyst is added sequentially in reaction tube with 1-2mL Dimethyl sulfoxide (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 compounds (I)；
Shown in imidazo [1,5-a] the N- heterocyclic compounds 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- furyls or aliphatic group, wherein aliphatic group are n-propyl；
Shown in the diaryl disulfide structure such as formula (III)：
In formula (III)：R3For methyl, methoxyl group or nitro；
Material molar ratio is：Imidazo [1,5-a] N- heterocyclic compounds (II): diaryldisulfide (III): catalyst=1: 0.6-1∶0.1-0.2；
The catalyst is iodine.
2. the synthetic method of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds according to claim 1, feature exist In the heating temperature is 110 DEG C, reaction time 10h.
3. the synthetic method of 3- arylthios imidazo [1,5-a] N- heterocyclic compounds according to claim 1, feature exist In the dimethyl sulfoxide (DMSO) (DMSO) is 1.5mL.
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