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Naphthoimidazopyridine compound and preparation method thereof

A technology of naphthimidazoles and compounds, which is applied in the field of naphthimidazopyridine compounds and their preparation, can solve the problems of poor stability, low atom economy, expensive substrates, etc., and achieve the effect of easy purification and good solubility

Inactive Publication Date: 2014-11-19
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For example CN103833754A provides a utilization of photocatalytic ring closure reaction to synthesize aromatic condensed ring compound; bifunctional aromatic compound and internal alkyne ring formation reaction, but the method substrate is expensive, poor stability, needs to be prepared in advance, atom economy is low ( Org.Lett.2004,6,2429; J.Org.Chem.2000,65,6944; J.Am.Chem.Soc.1999,121,5827); Cyclization of monofunctional aromatic compounds with internal alkynes , the substrate of this method is expensive, requires multi-step synthesis, and the generated by-products are not environmentally friendly (Organometallics 1987,6,1941; J.Org.Chem.2003,68,6836; J.Am.Chem.Soc .2002, 124, 12680; J.Org.Chem.2007, 72, 5362; J.Org.Chem.2008, 73, 298; Org.Lett.2009, 11, 5198)

Method used

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  • Naphthoimidazopyridine compound and preparation method thereof
  • Naphthoimidazopyridine compound and preparation method thereof
  • Naphthoimidazopyridine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Synthesis of the compound diphenylnaphthoimidazopyridine:

[0030]

[0031] Add 0.1mmol of 2-phenylpyrido[1,2-a]imidazole, 0.2mmol of tolan, 0.005mmol of [{RhCl 2 Cp*} 2 ], and 0.12 mmol of Co(OAc) 2 4H 2 O, 1 mL of DMF (N,N-dimethylformamide). The reaction tube was sealed and reacted at 110° C. for 2 hours to obtain a black reaction solution. Concentrate the black reaction solution under reduced pressure, and separate by column chromatography (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether=1 / 4) to obtain the target product diphenylnaphthoimidazopyridine. Pale yellow solid, yield 92%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.98 (dd, J = 0.4, 8.0Hz, 1H), 7.85 (dt, J = 0.8, 9.2Hz, 1H), 7.73-7.69 (m, 1H), 7.62 (d, J = 8.0 Hz,1H),7.53-7.48(m,1H),7.34-7.31(m,4H),7.29(brs,1H),7.28-7.27(m,2H),7.25-7.24(m,2H),7.23- 7.19(m,3H),6.50(dt,J=1.2,7.0Hz,1H). 13 C NMR (100MHz, CDCl 3 ): δ (ppm) 148.0, 140.8, 138.6, 136.9, 133.6, 131.6, 131.4, 130.4, 128.5, 127.7...

Embodiment 2

[0033] Synthesis of compound bis(4-methylphenyl)naphthoimidazopyridine:

[0034]

[0035] Add 0.1mmol of 2-phenylpyrido[1,2-a]imidazole, 0.2mmol of 1,2-di(4-methylphenyl)acetylene, 0.005mmol of [{ RhCl 2 Cp*} 2 ], and 0.12 mmol of Co(OAc) 2 4H 2 O, 1 mL of DMF (N,N-dimethylformamide). The reaction tube was sealed and reacted at 110° C. for 2 hours to obtain a black reaction solution. Concentrate the black reaction solution under reduced pressure, and separate by column chromatography (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether = 1 / 4) to obtain the target product bis(4-methylphenyl)naphthimidazo pyridine. Pale yellow solid, yield 80%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.97 (d, J = 8.0Hz, 1H), 7.84 (d, J = 9.2Hz, 1H), 7.69 (t, J = 7.2Hz, 1H), 7.62 (d, J = 8.4Hz ,1H),7.49(t,J=7.6Hz,1H),7.35-7.28(m,2H),7.14(s,4H),7.08(s,2H),7.07(s,2H),6.50(t, J=6.4Hz,1H),2.38(s,3H),2.33(s,3H). 13 C NMR (100MHz, CDCl 3): δ (ppm) 148.0, 140.8, 137.2, 136.0, 135.6, ...

Embodiment 3

[0037] Synthesis of compound bis(4-methoxyphenyl)naphthoimidazopyridine:

[0038]

[0039] Add 0.1mmol of 2-phenylpyrido[1,2-a]imidazole, 0.2mmol of 1,2-di(4-methoxyphenyl)acetylene, 0.005mmol of [ {RhCl 2 Cp*} 2 ], and 0.12 mmol of Co(OAc) 2 4H 2 O, 1 mL of DMF (N,N-dimethylformamide). The reaction tube was sealed and reacted at 110° C. for 2 hours to obtain a black reaction solution. Concentrate the black reaction solution under reduced pressure, and separate by column chromatography (silica gel 200-300 mesh, eluent: ethyl acetate / petroleum ether=1 / 4) to obtain the target product bis(4-methoxyphenyl)naphthimidazole And pyridine. Pale yellow solid, 84% yield. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.96 (dd, J = 0.4, 8.0Hz, 1H), 7.84 (dt, J = 0.8, 9.2Hz, 1H), 7.72-7.68 (m, 1H), 7.64 (d, J = 8.4 Hz,1H),7.52-7.48(m,1H),7.38(d,J=7.2Hz,1H),7.31(ddd,J=1.2,6.8,9.2Hz,1H),7.15(d,J=8.8Hz ,2H),7.10(d,J=8.8Hz,2H),6.88(d,J=8.8Hz,2H),6.81(d,J=8.8Hz,2H),6.53(dt,J=1.2,6.8Hz ,1H),3....

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Abstract

The invention discloses a naphthoimidazopyridine compound and a preparation method thereof. According to the invention, 2-phenyl-pyrido[1,2-a]imidazole and diaryl acetylene are adopted as raw material; and with a catalysis / oxidation double C-H activation method, the naphthoimidazopyridine compound is successfully prepared. The synthesis method is simple, and yield is high. The compound provided by the invention has good solubility in different organic solvents, and is easy to purify. Because multi-substituted condensed ring compound is a type of important framework structure and is widely applied in the fields of organic semiconductor materials and luminescent materials, the compound and the method provided by the invention have great application value and social economic benefit. The compound and the method has certain potential to be widely applied in the field of organic materials.

Description

technical field [0001] The invention relates to the technical field of synthesis and application of organic compounds, in particular to a naphthoimidazopyridine compound and a preparation method thereof. Background technique [0002] Aromatic fused ring compounds are formed by fused aromatic rings. Such compounds have large conjugated systems, planarity and rigid structures. Aromatic fused ring compounds are widely used in fields such as organic field effect transistors, organic light-emitting diodes, photovoltaic cells, organic nonlinear optics, fluorescent probes, and laser dyes because of their special structures and physical and chemical properties. For example, CN103108875A provides a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using the compound. [0003] The traditional chemical synthesis methods of aromatic fused ring compounds, such as cyclodehydrogenation, cyclodehydrohalogenation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 郝新奇王炜刘文博时谈浩赵雪梅牛俊龙龚军芳宋毛平
Owner ZHENGZHOU UNIV
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