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Method for synthesizing bicycle aza ring fluorescent or phosphorescent compound

A synthesis method and compound technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve problems such as low efficiency, difficult synthesis, and many synthesis steps, and achieve mild reaction conditions, fewer reaction steps, and excellent yields Effect

Inactive Publication Date: 2008-01-30
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

This kind of skeleton structure is often difficult to synthesize by traditional methods or there are many synthesis steps and low efficiency.

Method used

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  • Method for synthesizing bicycle aza ring fluorescent or phosphorescent compound
  • Method for synthesizing bicycle aza ring fluorescent or phosphorescent compound
  • Method for synthesizing bicycle aza ring fluorescent or phosphorescent compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the synthesis of bicyclic nitrogen heterocyclic carbene compound 3a and 4a

[0050] Put Fischer carbene compound 1a (1.0 mmol), 3-methyl-2-pyrazolin-5-one 2a (1.0 mmol) into a 5 ml reaction flask, and add 3 ml of tetrahydrofuran (THF). The whole reaction device was stirred in a 50° C. oil bath for 30 minutes. After the reaction was completed, the reaction mixture could be separated and purified by column chromatography. The chromatographic column was a silica gel column. When the eluent was petroleum ether (30~60° C.) / dichloromethane ( The yield of purple fraction 3a was 35.1% when v / v, 4:1); the blue fraction was collected when the eluent was petroleum ether (30-60°C) / dichloromethane (v / v, 2:1) Fraction 4a yield was 23.4%.

Embodiment 2

[0051] Embodiment 2: the synthesis of bicyclic nitrogen heterocyclic carbene compound 3b and 4b

[0052] Put Fischer carbene compound 1b (1.0 mmol), 3-methyl-2-pyrazolin-5-one 2a (1.0 mmol) into a 5 ml reaction flask, and add 3 ml of tetrahydrofuran (THF). The whole reaction device was stirred in a 50° C. oil bath for 30 minutes. After the reaction was completed, the reaction mixture could be separated and purified by column chromatography. The chromatographic column was a silica gel column. When the eluent was petroleum ether (30~60° C.) / dichloromethane ( The yield of purple fraction 3b was 46.4% when v / v, 4:1); the blue fraction was collected when the eluent was petroleum ether (30~60°C) / dichloromethane (v / v, 2:1) The yield of fraction 4b was 23.0%,

Embodiment 3

[0053] Embodiment 3: the synthesis of bicyclic nitrogen heterocyclic carbene compound 3c and 4c

[0054] Put Fischer carbene compound 1a (1.0 mmol), 3-propyl-2-pyrazolin-5-one 2b (1.0 mmol) into a 5 ml reaction flask, and add 3 ml of tetrahydrofuran (THF). The whole reaction device was stirred in a 50° C. oil bath for 30 minutes. After the reaction was completed, the reaction mixture could be separated and purified by column chromatography. The chromatographic column was a silica gel column. When the eluent was petroleum ether (30~60° C.) / dichloromethane ( The yield of purple fraction 3c was 46.7% when v / v, 4:1); the blue fraction was collected when the eluent was petroleum ether (30-60°C) / dichloromethane (v / v, 2:1) The yield of fraction 4c was 16.0%.

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Abstract

The invention relates to a synthetic method of a dicyclic azacyclo fluorescence or phosphorescent compounds: a metal carbene compound with a dicyclic azacyclo structure skeleton is produced from a carbene compound and 2-pyrazoline-5-ketone through a cycloaddition reaction in an organic solvent, and cis- and trans- dicyclic azacyclo organic compounds are respectively prepared after oxidation and demetalization; wherein, the cis-dicyclic azacyclo compounds have strong fluorescence performance, which can be uses as a small molecule probe compound for the analysis and checking of protein and cell; trans-dicyclic azacyclo compound is a non-fluorescent compound and may has phosphorescence; the oxidant used is inorganic or organic oxidant, and the reaction solvent is polar or non-polar organic solvent. The invention is of simple operation, with material easy to be acquired, a few reaction steps, better efficiency and selectiveness than traditional method; in particularly, compared with traditional synthesis method, the invention can more easily synthesize asymmetrical dicyclic azocyclo bimane compound.

Description

technical field [0001] The invention relates to a method for synthesizing a bicyclic nitrogen heterocyclic compound with fluorescent or phosphorescent properties. technical background [0002] Such compounds with bicyclic nitrogen heterocyclic structures as shown in formula I were developed by Kosower et al. First synthesis (Kosower, E.M.; Pazhenchevsky, B.; Hershkowitz, H.J.Am.Chem.Soc. 1978, 102, 4983-4993). The method used is to first use CH on the β-position of ethyl acetoacetate. 3 Alkylation with Br, etc., followed by reaction with hydrazine to form 3-methyl-4-alkyl-2-pyrazolin-5-one, followed by chlorination of the 4-position of this pyrazolone with chlorine, and finally in Removal of HCl / N under alkaline conditions 2 Cyclization produces this bicyclic nitrogen heterocyclic compound. [0003] Formula I [0004] According to the structural characteristics of this compound, Kosower et al. called this compound 9,10-dioxabimane (abbreviated as bimane). Among them,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06
Inventor 余正坤郑兆艳韩秀文
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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