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Polysubstituted carbazole compound, preparation method and application thereof

A compound and selected technology, applied in organic chemistry, drug combination, pharmaceutical formulation, etc., can solve the problems of large substrate limitations, high reagent toxicity, cumbersome operation, etc., and achieve easy purification, simple operation, and promising application prospects Effect

Inactive Publication Date: 2015-07-01
RENMIN UNIVERSITY OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(Graebe, C.; Ullmann, F.Ann. 1896, 291, 16; Preston, R.W.G.; Tucker, S.H.; Cameron, G.M.L.J. Chem. Soc. C 1942, 500; Bucherer, H.T.J. Prakt. Chem. 1904, 69, 49; Drechsel, E.; J.Prakt.Chem.1858, 38, 69; Borsche, W.; Feise, M.Ber.Dtsch.Chem.Ges.1904, 20, 378.) These methods are cumbersome to operate and have large substrate limitations. Many substrates have to be pre-synthesized, and some methods use highly toxic reagents
These defects limit the use of existing methods in the synthesis of carbazole compounds

Method used

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  • Polysubstituted carbazole compound, preparation method and application thereof
  • Polysubstituted carbazole compound, preparation method and application thereof
  • Polysubstituted carbazole compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1, compound 1-phenyl-2-benzoylcarbazole shown in preparation formula I

[0032]

[0033] Add 6 mmol of compound indole shown in formula II to the dry Schlenk reaction tube of 100 mL at room temperature, then the reaction system is evacuated with a vacuum pump, and nitrogen is charged into the reaction system, and 5 mmol of compound 2-(2 -(tert-butoxy)-2-phenylethyl)-1,3-diphenylpropane-1,3-dione, 50 mL of dry acetonitrile and 2.5 mmol of accelerator trifluoromethanesulfonic acid HOTf were injected into the reaction in sequence system. Heat the above mixed solution at 85°C and continue to stir to carry out the rearrangement and cyclization reaction for 2 hours to complete the reaction to obtain a brown reaction mixed solution, then concentrate the mixed solution by rotary evaporation, and then separate it with an acidic silica gel column (silica gel: 200-300 purpose, the eluent is a mixed solution of ethyl acetate and petroleum ether with a volume ratio of...

Embodiment 2

[0041] Embodiment 2: Compound 1-phenyl-2-benzoyl-6-methylcarbazole shown in preparation formula I

[0042]

[0043]According to the steps of Example 1, only the indole used is replaced by the compound 5-methylindole 2.4mmol shown in the formula II, the amount of the compound shown in the formula III1 is replaced by 2.0mmol, and the amount of trifluoromethanesulfonic acid HOTf is replaced by 1mmol, the amount of solvent was replaced by 20mL to obtain 1-phenyl-2-benzoyl-6-methylcarbazole with a yield of 70%.

[0044] The NMR and mass spectrometry data of this compound are as follows:

[0045] 1 H NMR (400MHz, CDCl3) δ8.09(d, J=8.0Hz, 1H), 8.07(br, 1H), 7.95(s, 1H), 7.71-7.69(m, 2H), 7.43-7.39(m, 4H),7.36-7.32(m,2H),7.31-7.27(m,5H),2.55(s,3H);

[0046] 13 C NMR (100MHz, DMSO-d6) δ198.5, 139.8, 138.2, 138.1, 136.7, 135.9, 133.2, 130.2, 130.0, 128.9, 128.7, 128.3, 127.9, 124.5, 124.3, 122.6, 120.6, 119.3, 112

[0047] HRMS calcd for C 26 h 20 NO(M+H) + :362.1542;found:36...

Embodiment 3

[0049] Embodiment 3: Compound 1-phenyl-2-benzoyl-6-hydroxycarbazole shown in preparation formula I

[0050]

[0051] According to the steps of Example 1, only 6 mmol of compound indole shown in formula II was replaced by 10 mmol of compound 5-oxindole shown in formula II, and the resulting product was a yellow powder pure product 1-phenyl-2-benzoyl- 6-Hydroxycarbazole in 64% yield.

[0052] The NMR and mass spectrometry data of this compound are as follows:

[0053] 1 H NMR(400MHz,DMSO-d6)δ10.66(br,1H),9.05(s,1H),8.11(d,J=8.0Hz,1H),7.59-7.57(m,2H),7.52(J= 2.2Hz,1H),7.47(t,J=7.4Hz,1H),7.37-7.30(m,7H),7.27-7.22(m,1H),7.17(d,J=8.0Hz,1H),6.95( dd,J=8.3Hz,2.4Hz,1H);

[0054] 13 C NMR(100MHz,DMSO-d6)δ198.6,151.3,138.5,138.2,136.8,135.7,133.2,130.2,129.9,128.6,127.8,124.5,124.2,123.1,119.4,118.8,116.7,112.37,105

[0055] HRMS calcd for C 25 h 18 NO 2 (M+H) + :364.1335;found:364.1332.

[0056] As can be seen from above, this product structure is correct, is the target co...

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Abstract

The invention discloses a polysubstituted carbazole compound and its derivative, a preparation method and application thereof. The compound has a structural general formula shown as formula I. The preparation method comprises: in a nitrogen atmosphere, mixing a compound shown as formula II, a compound shown as formula III and an accelerator evenly in organic solvent to carry out rearrangement cyclization reaction to obtain the compound shown as formula I. The method provided by the invention directly uses the industrial raw material indole and its derivative to construct the multi-functionalized carbazole compound. The method is easy to operate, can efficiently synthesize the multi-functionalized carbazole compound by one-step reaction directly, and the product is easy to separate and purify. Being pioneering, the method has optimistic application prospects in medicines, pesticides, materials and other fields. (formula I, formula II and formula III).

Description

technical field [0001] The invention relates to a multi-substituted carbazole compound and its preparation method and application. Background technique [0002] Carbazole, English carbazole, is an important class of nitrogen-containing heterocyclic compounds and an intermediate of many fine chemicals, which can be used in the synthesis of plastics, pesticides, insecticides, medicines, and new polymer materials. In the field of organic chemistry and polymer chemistry, the field of materials chemistry has a wide range of applications. Many drugs contain carbazole structures in their molecular skeletons, such as Carbazomycin B (1), which has anti-influenza effects. Ellipticine (2), is an antineoplastic agent. Rimcazole (3), has a good effect on the treatment of neurological diseases. [0003] [0004] The synthetic method of traditional carbazole compounds such as figure 1 As shown, there are mainly: (1) Graebe-Ullmann reaction. (2) Bucherer carbazole synthesis. (3) Bo...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88A61K31/403A61P35/00
CPCC07D209/86C07D209/88
Inventor 李志平郑晓建
Owner RENMIN UNIVERSITY OF CHINA
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