Silver-catalyzed synthesis of bis-heterocyclic molecules and bis-heterocyclic molecules with fluorescence activity

A biheterocyclic and molecular technology, applied in the field of new structure biheterocyclic fluorescent molecules, can solve the problem of high synthesis cost and achieve the effect of high cross-coupling selectivity and high yield

Inactive Publication Date: 2013-05-08
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Owing to having used the palladium catalyst of 10mol% in the reaction, the AgF of 200mol% and the Cu(OAc) of 200mol% 2 As an additive, so the synthesis cost is high

Method used

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  • Silver-catalyzed synthesis of bis-heterocyclic molecules and bis-heterocyclic molecules with fluorescence activity
  • Silver-catalyzed synthesis of bis-heterocyclic molecules and bis-heterocyclic molecules with fluorescence activity
  • Silver-catalyzed synthesis of bis-heterocyclic molecules and bis-heterocyclic molecules with fluorescence activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 25mL reaction flask, add AgF (5mg, 0.04mmol), Cu(OAc) 2 (73mg, 0.4mmol), CsF (91mg, 0.6mmol), 2a (53mg, 0.3mmol), after replacing the reaction gas atmosphere with oxygen, add 1a (27mg, 0.2mmol) and 2 ml of DMSO, and stir at room temperature for 2 minutes Afterwards, it was placed in an oil bath at 130°C to start the reaction, and the reaction was tracked by TLC. After the reaction was completed (about 24h), silica gel column chromatography was carried out for separation and purification, and the eluent was petroleum ether (60-90C) / ethyl acetate / triethylamine (v / v / v, 100:10:1) to obtain the target Product 10a (49 mg, 80% yield).

[0029] Formulate compound 10a into 5 × 10 -6 moles / liter of chloroform solution. This solution emits a dazzling blue luster under 365nm ultraviolet light irradiation, and has fluorescence activity.

[0030]Referring to the ATCC cell culture method, in DMEM (Dublecco's Minimum Essential Medium) medium (containing 1% dimethylmethylene L...

Embodiment 2

[0032] The reaction steps were the same as in Example 1, except that 2b (59 mg, 0.3 mmol) was used instead of 2a to obtain the target product 10b (41 mg, yield 63%).

Embodiment 3

[0034] The reaction steps were the same as in Example 1, except that 2c (64 mg, 0.3 mmol) was used instead of 2a to obtain the target product 10c (62 mg, yield 89%).

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Abstract

The invention discloses a synthesis method of bis-heterocyclic molecules and a series of fluorescence functional molecules with a novel bis-heterocyclic structure. Under the action of a catalyst silver fluoride, an additive copper acetate and an additive silver fluoride, oxazole, thiazole, imidazole, or a derivative of them can undergo a cross-coupling reaction so as to obtain new bis-heterocyclic molecules. The compounds have significant fluorescence activity. The synthesis reaction involved in the invention has the characteristics of easily available raw materials, and simple and efficient operation.

Description

technical field [0001] The invention relates to a synthesis method of a biheterocyclic molecule and a novel structural biheterocyclic fluorescent molecule. Background technique [0002] Organic biheterocyclic molecules, especially oxazole, thiazole, and imidazole compounds and their derivatives are widely used in the field of medicine and photoelectric functional materials. The traditional method of synthesizing such compounds is to prepare one heterocyclic molecule as its halide, prepare the other heterocyclic molecule as the corresponding organometallic compound, and then obtain the corresponding biheterocyclic compound by transition metal-catalyzed cross-coupling. This method requires pre-conversion of heterocyclic molecules into corresponding active species, such as halides and organometallic compounds, and the experimental operation is tedious. In recent years, it has been reported in the literature that the C-H bond of two heterocyclic molecules can be directly activa...

Claims

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Application Information

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IPC IPC(8): C07D417/04C07D277/62C09K11/06
Inventor 许兆青余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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