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Nitrogen and oxa polycyclic aromatic hydrocarbon and synthesis method thereof

A technology of a hetero-fused ring aromatic hydrocarbon and a synthesis method, which is applied in the field of organic synthetic chemistry, can solve the problems of complex substrate synthesis, limited product structure, single synthesis method, etc., and achieves the effects of economical steps, good yield and simple operation.

Inactive Publication Date: 2022-07-08
HENAN AGRICULTURAL UNIVERSITY
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Problems solved by technology

[0005] Aiming at technical problems such as the single synthesis method of existing fused heterocyclic aromatic hydrocarbons, complicated substrate synthesis and limited product structure, the present invention proposes a nitrogen and oxygen heterocondensed aromatic hydrocarbon and a synthesis method thereof. The synthesis provides a simple and effective synthetic method, and the method has the characteristics of mild reaction conditions, simple operation, atom economy, step economy, strong functional group tolerance and good yield.

Method used

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  • Nitrogen and oxa polycyclic aromatic hydrocarbon and synthesis method thereof
  • Nitrogen and oxa polycyclic aromatic hydrocarbon and synthesis method thereof
  • Nitrogen and oxa polycyclic aromatic hydrocarbon and synthesis method thereof

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Embodiment 1

[0043]

[0044] Under nitrogen, 3-arylbenzoxazine compound 1a (0.20 mmol), diazo compound 2a (0.44 mmol), [Cp*RhCl 2 ] 2 (4mol%), AgSbF 6 (16 mol%), MesCOOH (0.4 mmol) and solvent DCE (2.0 mL) were added to a 10 mL sealed tube, and reacted in a reaction module of 80 degrees for 10 h. After the reaction was completed, the solvent was removed under reduced pressure, and the target product 5 was obtained by separation with a silica gel column. ,12-Dimethylisoquinoline[2,1,8-mna]phenoxazine-4,13-dicarboxylate (3aa), all eluents were petroleum ether ethyl acetate and dichloromethane It is formulated according to the ratio of 30:1:1. Product data characterization: tan liquid, 78% yield. The NMR spectrum of the product is figure 1 and 2 shown, 1 H NMR (400MHz, CDCl 3 )δ7.23(d,J=8.6Hz,1H),7.11(t,J=8.0Hz,1H),7.03–6.97(m,1H),6.94(t,J=7.6Hz,1H),6.89( d, J=7.7Hz, 1H), 6.82 (d, J=7.9Hz, 1H), 6.77 (d, J=7.3Hz, 1H), 4.49–4.38 (m, 4H), 2.33 (s, 6H), 1.45–1.40(m,6H). 13 CNMR (101...

Embodiment 2

[0046]

[0047] Under nitrogen, 3-arylbenzoxazine compound 1b (0.20 mmol), diazo compound 2a (0.44 mmol), [Cp*RhCl 2 ] 2 (4mol%), AgSbF 6 (16 mol%), MesCOOH (0.4 mmol) and solvent DCE (2.0 mL) were added to a 10 mL sealed tube, and reacted in a reaction module at 80 degrees for 10 h. After the reaction was completed, the solvent was removed under reduced pressure, and the target product 7 was obtained by separation with a silica gel column. -Bromo-5,12-dimethylisoquinoline[2,1,8-mna]phenoxazine-4,13-dicarboxylate diethyl ester (3ba), all eluents were petroleum ether ethyl acetate and dichloromethane in a ratio of 30:1:1. Characterization of product data: tan solid, 98% yield, melting range: 119-120°C. The NMR spectrum of the product is image 3 and 4 shown, 1 H NMR (400MHz, CDCl 3 )δ7.26(t,J=8.3Hz,2H),7.14(t,J=8.0Hz,1H),6.86(t,J=8.0Hz,1H),6.79(dd,J=7.5,4.6Hz, 2H), 4.49–4.39(m, 4H), 2.44(s, 3H), 2.33(s, 3H), 1.45–1.40(m, 6H). 13 C NMR (101MHz, CDCl 3 )δ168.6,167.6,...

Embodiment 3

[0049]

[0050] Under nitrogen, 3-arylbenzoxazine compound 1c (0.20 mmol), diazo compound 2a (0.44 mmol), [Cp*RhCl 2 ] 2 (4mol%), AgSbF 6 (16mol%), MesCOOH (0.4mmol) and solvent DCE (2.0mL) were added to a 10mL sealed tube, and the reaction was carried out in a reaction module at 80 degrees for 10h. After the reaction was completed, the solvent was removed under reduced pressure, and the target product 8 was obtained by separation with a silica gel column. - Diethyl fluoro-5,12-dimethylisoquinoline[2,1,8-mna]phenoxazine-4,13-dicarboxylate (3ca), all eluents were petroleum ether ethyl acetate and dichloromethane in a ratio of 30:1:1. Product Data Characterization: Yellow solid, 89% yield, melting range: 104-105°C. The NMR spectrum of the product is Figure 5 and 6 shown, 1 H NMR (400MHz, CDCl 3 )δ7.26(t,J=8.3Hz,2H),7.14(t,J=8.0Hz,1H),6.86(t,J=8.0Hz,1H),6.79(dd,J=7.5,4.6Hz, 2H), 4.49–4.39(m, 4H), 2.44(s, 3H), 2.33(s, 3H), 1.45–1.40(m, 6H). 13 C NMR (101MHz, CDCl 3 )...

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Abstract

The invention provides nitrogen and oxa polycyclic aromatic hydrocarbon and a synthesis method thereof, which are used for solving the technical problems of single synthesis method, complex substrate synthesis, limited product structure and the like in the existing polycyclic aromatic hydrocarbon synthesis method. The synthesis method comprises the following steps: adding an oxazine compound 1, a diazo compound 2, a catalyst and an additive into a solvent in an inert atmosphere, and reacting in the inert atmosphere to obtain the polycyclic aromatic hydrocarbon compound 3 after the reaction is finished. The invention provides a simple and effective synthesis method for synthesis of polycyclic aromatic hydrocarbon containing multiple heteroatoms, and the method has the characteristics of mild reaction conditions, simple operation, atom economy, economical steps, strong functional group tolerance, good yield and the like. The obtained product has a wide industrial application prospect, and meanwhile, a new thought and a new method are provided for the fields of medicines, natural product synthesis, luminescent materials and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthetic chemistry, and in particular relates to a nitrogen, oxygen heterocyclic aromatic hydrocarbon and a synthesis method thereof. Background technique [0002] Polycyclic aromatic hydrocarbons refer to polycyclic aromatic hydrocarbon compounds composed of two or more aromatic hydrocarbons, which are widely used in pharmaceuticals, dyes and other industries. There are π-π interactions in the crystal arrangement of fused ring aromatic hydrocarbons, and an ordered stacking is formed between the molecules, which is used in organic optoelectronic devices (including organic field-effect transistors (Organic Field-Effect Transistor, OFET), organic solar cells (Organic Solar Cell, OSC) and organic light-emitting diodes (Organic Light-Emitting Diode, OLED, etc.), organic semiconductor materials and other fields have broad application prospects (Chem. Rev., 2007, 107, 926; Chem. Soc. Rev., 2010, 39, 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06
CPCC07D498/06C09K11/06G01N21/6428C09K2211/1033Y02E10/549
Inventor 樊良鑫张静静杨西发刘向阳
Owner HENAN AGRICULTURAL UNIVERSITY