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Pi-conjugated polycyclic amino isoquinoline compound, and synthesis method and application thereof

A technology of polycyclic aminoisoquinolines and compounds, applied in the fields of organic chemistry and materials science, to achieve the effects of long photoluminescence lifetime, good reaction step economy, and strong fluorescence quantum yield

Active Publication Date: 2021-06-29
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, oxidative [4+2] cyclizations using these electron-deficient internal alkenes are very challenging because the two coupling reagents prefer aza-Michael addition reactions

Method used

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  • Pi-conjugated polycyclic amino isoquinoline compound, and synthesis method and application thereof
  • Pi-conjugated polycyclic amino isoquinoline compound, and synthesis method and application thereof
  • Pi-conjugated polycyclic amino isoquinoline compound, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The synthesis of embodiment 1π conjugated polycyclic aminoisoquinoline compounds

[0047] (1) Compound 3 was synthesized by oxidative amination reaction: the weighed arylamidine 1 (0.25mmol, 1.0 equivalent), maleimide 2 (0.50mmol, 2.0 equivalent), Cu(OAc) 2 (9.0mg, 20.0mol%) and 2,2'-bipyridine (11.7mg, 30.0mol) were placed in a dry reaction tube, and after vacuum-oxygen replacement (three times) was carried out through a double row tube, anhydrous DCE (1.0 mL), stirred at 120 °C for 12 h under an atmosphere of oxygen (1 atm). The solvent was evaporated in vacuo at room temperature, and the remaining residue was purified by column chromatography on silica gel (n-Hexane / EtOAc as eluent) to afford starting material 3.

[0048] (2) Synthetic compound 4: Place the weighed raw material 3 (0.15mmol, 1.0 equivalent), TEMPO (0.03mmol, 20mol%) in a dry reaction tube, and carry out vacuum-oxygen replacement (three times) by double row tubes ), isopropanol (3.0 mL) was added, an...

Embodiment 2

[0265] Example 2 explores the influence of solvent selection on the synthesis of intermediate compounds in the process of oxidative amination reaction

[0266] With reference to the preparation process of Example 1, when the conditions shown in Table 1 were selected for each reaction condition, the results of the corresponding synthetic intermediate compound 3-a were as shown in Table 1:

[0267] Table 1 The results of the synthesis of intermediate compound 3-a in different oxidative amination reaction solvent systems

[0268]

Embodiment 3

[0269] Example 3 explores the influence of catalyst selection on the synthesis of intermediate compounds in the process of oxidative amination reaction

[0270] With reference to the preparation process of Example 1, when the conditions shown in Table 2 were selected for each reaction condition, the results of the corresponding synthetic intermediate compound 3-a were as shown in Table 2:

[0271] Table 2 The results of the synthesis of intermediate compound 3-a by different oxidative amination reaction catalytic systems

[0272]

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Abstract

The invention discloses a pi-conjugated polycyclic amino isoquinoline compound, and a synthesis method and application thereof, and belongs to the field of organic chemistry and material science. The provided method for synthesizing the novel pi-conjugated polycyclic amino isoquinoline compound has good atom and reaction step economy, high efficiency and greenness, and the structure of the synthesized novel pi-conjugated polycyclic amino isoquinoline compound has higher fluorescence quantum yield and longer photoluminescence life, can be used in the fields of small-molecule fluorescent markers, novel photoelectric materials and the like, and has a good application prospect.

Description

technical field [0001] The invention relates to a π-conjugated polycyclic aminoisoquinoline compound and its synthesis method and application, belonging to the fields of organic chemistry and materials science. Background technique [0002] Fused N-containing heterocyclic rings have become important structural units in materials science applications due to their various special optoelectronic and electromagnetic properties. Under such circumstances, there is a continuous and strong demand for the design and efficient synthesis of novel N-containing heterocycles. Among many synthetic approaches, transition metal-catalyzed activation of carbon-hydrogen bonds has recently been reconstituted as an increasingly viable tool for the preparation of fused N-containing heterocycles with extended π-conjugated systems. Despite the considerable progress, the use of transition metal catalysts, especially the use of noble metals Ru-, Rh-, Pd-, and Ir-complexes, makes this strategy still s...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06
CPCC07D471/04C09K11/06C09K2211/1044C09K2211/1007
Inventor 刘蕾李杰王大伟张钊
Owner JIANGNAN UNIV
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