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Polysubstituted indazine derivative and preparation method thereof

A multi-substitution and derivative technology, applied in the direction of organic chemistry, can solve the problems of cumbersome operation, and achieve the effects of simple operation, easy mass preparation, and no metal pollution.

Inactive Publication Date: 2020-07-24
SHENZHEN POLYTECHNIC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2016, Hu Huayou's research group used pyridine, α-halogenated carbonyl compounds and electron-deficient olefins to synthesize multi-substituted inzine derivatives in one pot. During the reaction process, an additional oxidant TEMPO needs to be added, and the operation is cumbersome (Transition-Metal-FreeSynthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant, Fei Shi, Y. Zhang, Z. Lu, X. Zhu, W. Kanb, X. Wang, H. Hu, Synthesis, 2016, 48, 413–420 )

Method used

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  • Polysubstituted indazine derivative and preparation method thereof
  • Polysubstituted indazine derivative and preparation method thereof
  • Polysubstituted indazine derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0023] The reaction formula of Example 1, the specifically used compound III-1 and compound II-1 and the structure of the product I-1 are shown in the following formula. Experiment shows that the present invention uses salt of wormwood and triethylamine as mixed base, and preferred organic solvent is methylene dichloride, and the highest yield of its reaction product is 68%, and the best raw material molar ratio is compound III: compound II: potassium carbonate : Triethylamine=1.0:4.0:2.0:2.0, wherein compound III is an equivalent value, and compound II needs to be in excess to ensure that compound III can react completely, and the optimal concentration of the solution is 0.1M.

[0024]

[0025] The specific experimental steps are: dissolve 127mg (0.50mmol, 1.0 equivalent) of compound III-1 and 168mg (2.0mmol, 4.0 equivalent) of compound II-1 in 5mL of dichloromethane, add 138mg (1.0mmol, 2.0 equivalent) ) of potassium carbonate, 101mg (1.0mmol, 2.0 equivalents) of triethyl...

Embodiment 2

[0029] The specific experimental steps for the preparation of compound I-2 to compound I-11 are the same as those for the preparation of compound I-1, and the structures of the raw materials used are as follows:

[0030]

[0031] The resulting product structure and data are characterized as follows:

[0032]

[0033] Product Ⅰ-2 is a yellow solid with a yield of 64%; melting point: 46-47°C. 1 H NMR (300MHz, CDCl 3)δ9.32(d, J=7.2Hz, 1H), 7.51(d, J=9.2Hz, 1H), 7.04(ddd, J=9.2Hz, 6.8Hz, 1.2Hz, 1H), 6.84(td, J =7.0,1.6Hz,1H),4.10(q,J=7.2Hz,2H),3.92(s,3H),3.86(s,3H),3.78(s,2H),1.20(t,J=6.8Hz ,3H); 13 C NMR (75MHz, CDCl 3 )δ169.9, 165.5, 160.0, 134.2, 126.1, 126.0, 121.6, 116.7, 113.5, 110.4, 106.4, 60.2, 51.5, 50.8, 29.3, 13.5; ESI-HRMS m / z calcd for C 16 h 18 NO 6 [M+H] + 320.1129,found 320.1123.

[0034] Product Ⅰ-3 was a yellow oily liquid with a yield of 60%. 1 H NMR (400MHz, CDCl 3 )δ9.33(d, J=6.8Hz, 1H), 7.53(d, J=8.8Hz, 1H), 7.06(t, J=7.4Hz, 1H), 6.84(t, J=...

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Abstract

The invention mainly aims to provide a polysubstituted indazine derivative and a preparation method thereof. The method realizes one-step simple and efficient synthesis of indazine derivatives from propiolate compounds and pyridine sulfur-containing ylide salt at 30 DEG C by using triethylamine and potassium carbonate as a mixed alkali and using common solvent dichloromethane as a solvent. The method has the advantages of simple reaction operation, mild conditions, no metal pollution, and easy realization of large-scale preparation; and a new method for synthesizing indazine without transitionmetal catalysis is developed.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to multi-substituted inzine derivatives and a preparation method thereof. Background technique [0002] Nitrogen exists widely in nature and organisms, and the representative nitrogen-containing compounds are natural organic alkaloids, which play an extremely important role in the field of medicine. As an important branch of nitrogen-containing aromatic heterocyclic compounds, indazine has potential biological activity and has become the core structural unit of many drug molecules. Therefore, its synthesis and derivation research has attracted extensive attention from organic chemists and medicinal chemists, and its development is highly efficient. The new method of synthesizing inzine compounds has important academic significance and potential application prospects. In recent years, the synthesis of indolizines has attracted extensive attention from chemists. In 2016, Hu Huayou'...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 程斌
Owner SHENZHEN POLYTECHNIC
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