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A microwave synthesis method of 1,2,3,5-tetrasubstituted azocene compounds

A compound and azecene technology, which is applied in the field of microwave synthesis of 1,2,3,5-tetra-substituted azecene compounds, can solve the problems of low reaction efficiency, low atom utilization, and inability to popularize and apply industrially.

Active Publication Date: 2021-04-23
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Aiming at the lack of microwave synthesis of a 1,2,3,5-tetrasubstituted azocene compound in the prior art, the few technologies still have the disadvantages of low atom utilization rate, low reaction efficiency, and inability to be popularized and applied in industry The object of the present invention is to provide a microwave synthesis method of a 1,2,3,5-tetrasubstituted azocene compound with a new reaction mechanism, aiming to provide a high atomic efficiency and high yield, Low cost, no need for chromatographic purification, and a new synthetic method that is conducive to industrial production applications

Method used

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  • A microwave synthesis method of 1,2,3,5-tetrasubstituted azocene compounds
  • A microwave synthesis method of 1,2,3,5-tetrasubstituted azocene compounds
  • A microwave synthesis method of 1,2,3,5-tetrasubstituted azocene compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1～4

[0056] Following examples 1~4 all react by following reaction equation:

[0057]

[0058] The specific operation steps are: in a 50mL round bottom flask, add alkynes (30mmol), trimethylcyanosilane (30mmol), formamides (30mmol) and ammonium iodide (3mmol) successively, and the resulting mixture is heated in a microwave 400W in the reactor, stirring and reacting for 10 minutes under the condition of temperature control of 100°C. After the reaction, 30 mL of ethyl acetate was used to dissolve the reactant, the solution was washed with saturated brine, the liquid was separated, the organic phase liquid was concentrated in vacuo, dried in vacuo to calculate the weight.

Embodiment 1

[0060] raw material: TMSCN,

[0061] Target product:

[0062] Yield: 94%.

[0063] 1-ethyl-5-methyl-3-phenyl-1H-pyrrole-2-carbonitrile

[0064] 1 H NMR (400MHz, CDCl 3 )δ7.69-7.62(m,2H),7.40(dd,J=15.9,8.1Hz,2H),7.29(t,J=7.4Hz,1H),6.17(s,1H),4.06(q,J =7.3Hz, 2H), 2.31(s, 3H), 1.42(t, J=7.3Hz, 3H).

[0065] 13 C NMR (100MHz, CDCl 3 )δ135.1, 134.6133.2, 128.9, 128.6, 128.5, 127.6, 126.6, 115.4, 107.8, 99.2, 40.9, 16.3, 12.4.

Embodiment 2

[0067] raw material: TMSCN,

[0068] Target product:

[0069] 5-ethyl-3-phenyl-1-propyl-1H-pyrrole-2-carbonitrile

[0070] Yield: 95%.

[0071] 1 H NMR (400MHz, CDCl 3 )δ7.67(dd, J=8.4,1.6Hz,2H),7.39(t,J=7.2Hz,2H),7.36(s,1H),6.20(s,1H),3.98(t,J=7.6 Hz, 2H), 2.55(t, J=7.2Hz, 2H), 1.77-1.70(m, 4H), 1.44-1.40(m, 2H), 1.04(t, J=7.6Hz, 3H), 0.98(t ,J=7.6Hz,3H);

[0072] 13 C NMR (100MHz, CDCl 3 )δ134.3, 133.1, 128.8, 128.4, 128.4, 127.4, 126.5, 115.4, 106.4, 99.4, 45.7, 33.2, 28.4, 21.7, 19.9, 13.9, 13.7.

[0073] HRMS (ESI) calcd for C 16 h 19 N 2 [M+H] + :239.1548, found 239.1550.

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Abstract

The invention discloses a microwave synthesis method for 1,2,3,5-tetrasubstituted azocene compounds, which comprises equimolar amounts of aromatic terminal alkynes, trimethylcyanosilane, formamide compounds, and catalysts Catalyzed reaction assisted by microwave to obtain 1,2,3,5-tetrasubstituted azocene compounds in one pot and one step. The method has good product selectivity, high yield, simple separation process, low catalyst cost, environmental friendliness, and is beneficial to industrial production and application.

Description

technical field [0001] The invention belongs to the technical field of organic intermediate synthesis, and in particular relates to a microwave synthesis method of 1,2,3,5-tetrasubstituted azocene compounds. Background technique [0002] Azacene compounds are an important class of five-membered nitrogen-containing heterocyclic compounds, and are commonly used pharmacophore in the field of drug research. The derivatives of the parent structure have various physiological and pharmacological activities, and are widely used as anticancer drugs, Antineoplastic drugs, antibacterial drugs, etc. are a class of potential multipurpose lead compounds with broad development and application prospects. [0003] It is possible to obtain drugs with better potential drug effects by modifying the group of the azacene ring. For example, the cyano group has special properties, and it is possible to obtain drug intermediates with various potential drug effects by modifying the cyano group to th...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07D471/04
CPCC07D207/34C07D471/04
Inventor 龚绍峰王靖婷彭莎丁满花
Owner HUNAN UNIV OF SCI & ENG
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