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Preparation method of N-substituted-1H-pyrrole

A technology of C-140 and aromatic heterocycles, which is applied in the field of preparation of pyrrole derivatives, and can solve problems such as side reactions, unstable raw materials, and high prices

Inactive Publication Date: 2013-04-03
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] 1,4-bis-(dimethylamino)-1,3-butadiene, 1,4-dichloro-1,4-dimethoxybutane, 2-chlorocyclopropanaldehyde, 3 - Pyrroline, etc. are expensive and difficult to obtain, raw materials such as pyrrole and 3-pyrrole are unstable, and need to be reacted under inert conditions
[0019] Chinese invention patent (CN 102180824 A) discloses that an aromatic aldehyde and 4-hydroxy-L-proline are refluxed in N,N-dimethylformamide under the catalysis of benzoic acid to synthesize N-(arylmethyl ) pyrrole method, the yield is 84%, but the solubility of 4-hydroxy-L-proline in DMF is not high, and it is easy to produce side reactions due to excessive aldehydes, so it needs to be heated to 140 ° C, and aromatic aldehydes are slowly added dropwise. Response, cumbersome to operate

Method used

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  • Preparation method of N-substituted-1H-pyrrole
  • Preparation method of N-substituted-1H-pyrrole
  • Preparation method of N-substituted-1H-pyrrole

Examples

Experimental program
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Effect test

Embodiment 1

[0046] The preparation of embodiment 1 N-benzyl-1H-pyrrole

[0047]

[0048] FeSO 4 .7H 2 O (0.021g, 0.15mmol), N,N-dimethylethylenediamine (0.027g, 0.3mmol) were suspended in 10ml of toluene, stirred at room temperature for 10min, then added 4-(benzoyloxy)-1 -benzyl-pyrrolidine-2-carboxylic acid (0.33g, 1mmol), di-tert-butyl peroxide (0.2g, 1.4mmol), reflux reaction overnight, the reaction solution was decompressed to remove the solvent, silica gel column chromatography (washing Off-line (petroleum ether / ethyl acetate = 10:1 (v / v)) to obtain 0.10 g of N-benzyl-1H-pyrrole, a colorless liquid, with a yield of 64%; 1 HNMR (400MHz, CDCl 3 )δppm5.18(s, 2H), 6.36(t, J=2.01, 2.01Hz, 2H), 6.84(t, J=1.99, 1.99Hz, 2H), 7.26(d, J=7.08Hz, 2H), 7.45(m, 3H); 13 C NMR (101MHz, CDC1 3)δppm 53.43, 108.68, 121.30, 127.14, 127.77, 128.86, 138.371; MS, m / z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1 (7.7), 156.1 (8.3), 92.1 (6.5) .

Embodiment 2

[0049] The preparation of embodiment 2 N-benzyl-1H-pyrrole

[0050]

[0051] Except replacing FeSO with CuBr (0.022g, 0.15mmol) 4 .7H 2 Except for O (0.021g, 0.15mmol), the others were the same as in Example 1 to obtain 0.10g of N-benzyl-1H-pyrrole, a colorless liquid, with a yield of 62%; 1 H NMR (400MHz, CDC1 3 )δppm5.18(s, 2H), 6.36(t, J=2.01, 2.01Hz, 2H), 6.84(t, J=1.99, 1.99Hz, 2H), 7.26(d, J=7.08Hz, 2H), 7.45(m, 3H); 13 C NMR (101MHz, CDC1 3 )δppm 53.43, 108.68, 121.30, 127.14, 127.77, 128.86, 138.371; MS, m / z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1, 7.7), 156.1 (8.3), 92.1 (6.5) .

Embodiment 3

[0052] Example 3 Preparation of N-(4-trifluoromethyl-benzyl)-1H-pyrrole

[0053]

[0054] Except that 4-(benzoyloxy)-1-(4-(trifluoromethyl)-benzyl)pyrrolidine-2-carboxylic acid (0.39 g, 1 mmol) was used instead of 4-(benzoyloxy) -1-(4-benzyl)pyrrolidine-2-carboxylic acid (0.33g, 1mmol), the others are the same as in Example 1 to obtain N-(4-trifluoromethyl-benzyl)-1H-pyrrole 0.14 g, yellow liquid, yield 63%; 1 NMR (400MHz, CDCl 3 )δppm 5.19(s, 2H), 6.31(s, 2H), 6.76(s, 2H), 7.25(d, J=7.96Hz, 2H), 7.64(d, J=7.97Hz, 2H); 13 C NMR (101MHz, CDC1 3 ) δppm 52.80, 109.10, 121.24, 125.74 (q, J=3.77, 3.75, 3.75Hz, 1C), 127.10, 142.43; ESI for [M+H]: calculated, 226.0844; found, 226.0843.

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Abstract

The invention relates to a method for preparing N-substituted-1H-pyrrole. N-substituted- 4-benzoyloxyproline used as a raw material is subjected to oxidative decarboxylation aromatization under the action of an oxidizer in a system using metal as a catalyst and amine as a ligand, thereby generating the target compound N-substituted-1H-pyrrole. The method provided by the invention has the advantages of cheap and accessible raw material, novel method, high efficiency and the like.

Description

technical field [0001] The invention relates to a method for preparing pyrrole derivatives, in particular to a method for preparing N-substituted-1H-pyrrole derivatives. Background technique [0002] Pyrrole compounds have various biological activities such as antibacterial, antiviral, and antitumor, and toniporphine compounds, which are natural compounds with anticancer activity, are pyrrole derivatives. In recent years, it has been found that N-(arylmethyl)pyrrole compounds have an inhibitory effect on HIV-lgp41 (J.Med.Chem., 2008, 5:7843-7854; Bioorg.Med.Chem., 2008, 16:3039 -3048), this type of structure is also contained in many natural heterocyclic compounds and functional materials (JOrg. Chem., 2001, 66: 550-556; J. Org. Chem. 2001, 66: 4058-4061). [0003] The preparation of N-arylpyrrole is usually dehydrogenated by pyrrole in tetrahydrofuran or ionic liquid under the action of Na, K, or n-BuLi and reacting with equimolar halogenated hydrocarbons. [0004] [...

Claims

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Application Information

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IPC IPC(8): C07D207/323C07D207/325C07D207/327C07D405/06C07D409/06C07D401/06
Inventor 虞心红翟民杨丛斌朱虹刘霜
Owner EAST CHINA UNIV OF SCI & TECH
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