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Preparation method of imidazo (1, 5-alpha) pyridine derivative DH2PIP and complex thereof

An imidazo and derivative technology is applied in the field of preparation of imidazo[1,5-α]pyridine derivatives DH2PIP and its complexes, which can solve the problems of harsh reaction conditions and high reaction cost, and achieves low cost and preparation method. Simple, wide-ranging effects

Inactive Publication Date: 2017-07-21
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the invention is to provide imidazo[1,5-α]pyridine derivatives DH 2 The preparation method of PIP and its complex solves the problems of harsh reaction conditions and high reaction cost

Method used

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  • Preparation method of imidazo (1, 5-alpha) pyridine derivative DH2PIP and complex thereof
  • Preparation method of imidazo (1, 5-alpha) pyridine derivative DH2PIP and complex thereof
  • Preparation method of imidazo (1, 5-alpha) pyridine derivative DH2PIP and complex thereof

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preparation example Construction

[0029] The invention provides imidazo[1,5-α]pyridine derivative DH 2 The preparation method of PIP, the method comprises the steps:

[0030] (1) Preparation of intermediate product M;

[0031] (2) Preparation of product DH 2 PIP.

[0032] In order to make the above objects, features and advantages of the present invention more comprehensible, the present invention will be further described in detail below in conjunction with specific embodiments.

[0033] Imidazo[1,5-α]pyridine derivative DH 2 The preparation method of PIP comprises:

[0034] Step 1: Weigh 2,6-pyridinedicarboxylic acid into a flask, add ethyl n-butyrate and stir to dissolve, slowly add 2-aminomethylpyridine while stirring, stir at room temperature for half an hour, then add tripropylene base phosphoric anhydride, and then put it into a 130°C oil bath and heat it to reflux for six hours. After cooling to room temperature, the reacted liquid is divided into upper and lower layers, and the lower layer is ret...

Embodiment 1

[0044] This implementation case shows the preparation method of imidazo[1,5-α]pyridine derivative DH2PIP (C19N5H13) according to the following steps:

[0045] Accurately weigh 2,6-pyridinedicarboxylic acid (20 mmol, 3.34 g) into a 250 mL round-bottomed flask, add 20 mL of ethyl n-butyrate and stir to dissolve, slowly add 2-aminomethylpyridine (40 mmol , 4.32 g), stirring while adding, after stirring at room temperature for half an hour, add 10 mL of tripropylphosphoric anhydride (T3P), put it in a 130 ℃ oil bath and heat to reflux for six hours, after cooling to room temperature, it can be It can be seen that the reacted liquid is divided into upper and lower layers, the upper layer is dark yellow clear liquid, and the lower layer is dark brown viscous. Post-treatment: use a straw to separate out the supernatant and discard it, keep the lower layer for use, add an appropriate amount of water to the lower layer, then adjust the pH with saturated sodium bicarbonate solution, sti...

Embodiment 2

[0049] This implementation case shows the preparation method of the complex [Cu(DH2PIP)Cl2] (C19H13N5Cl2Cu) of imidazo[1,5-α]pyridine derivative DH2PIP according to the following steps:

[0050] Accurately weigh the ligand DH2PIP (0.0397 g, 0.1 mmol) and copper chloride dihydrate (0.0171 g, 0.1 mmol), add them to the glass tube in turn, dissolve the mixture with 2 mL of absolute ethanol, put it in a constant temperature drying oven and heat up to 125 oC, under the action of autogenous pressure, keep the temperature at constant temperature for 2 days, turn off the oven, and let it cool down to room temperature naturally. Brownish yellow blocky crystals are formed. Filter, wash with absolute ethanol, and dry. Crystal yield: 70% (0.0310 g).

[0051] [Cu(DH2PIP)Cl2] (C19H13N5Cl2Cu) prepared in this example, the test results can be found in Figure 4 , Figure 4 It is the X-ray diffraction pattern of the complex [Cu(DH2PIP)Cl2] in the preparation method of the complex of imidazo[1...

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Abstract

The invention discloses a reparation method of imidazo (1, 5-alpha) pyridine derivative DH2PIP and a complex thereof. The method comprises the following steps: firstly weighing and putting 2, 6-pyridinedicarboxylic acid into a flask, adding ethyl butyrate, stirring and dissolving, dropwisely adding 2-picolylamine and stirring, adding tripropyl phosphoric anhydride, so as to obtain an intermediate product M, adding ethyl butyrate and the tripropyl phosphoric anhydride, obtaining a product DH2PIP after reaction, and then enabling the DH2PIP and metal chloride or metal bromide to be reacted, so as to obtain the DH2PIP complex. The DH2PIP and the complex thereof have the advantages that the preparation processes are simple and safe to operate, the raw materials are wide in source, and the cost is low.

Description

technical field [0001] The present invention relates to imidazo[1,5-α]pyridine derivatives DH 2 Preparation method of PIP and its complexes. Background technique [0002] Imidazo[1,5-α]pyridine belongs to nitrogen heterocyclic compounds. It is a large conjugated body with 9 centers and 10 electrons. Its 1 and 3 positions are relatively active and can be substituted by different substituents. The application value of its derivatives higher. [0003] The synthesis of transition metal complexes using imidazo[1,5-α]pyridine and its derivatives as ligands has aroused the interest of many chemical workers in the past two decades, mainly for the following important reasons: (1) as Photoelectric functional materials, etc., as organic thin-layer field-effect transistors (FETs), organic light-emitting diodes (OLEDs), etc.; (2) as nitrogen heterocyclic carbene precursors (NHCs), which are important in the synthesis of valuable transition metal catalysts Application; (3) Due to its b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D471/04C07F1/08C07F15/04C07F15/02C07F13/00
CPCC07D519/00C07B2200/13C07D471/04C07F1/005C07F13/005C07F15/025C07F15/045
Inventor 李亚红张瑾秦亚茹崔燕峰陆宁潘样丹姜志垒
Owner SUZHOU UNIV
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