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Indole derivative with pyrrolidone structure and preparation method thereof

A technology of indole derivatives and pyrrolidone, which is applied in the field of indole derivatives, can solve the problems of increasing production costs and infeasibility, and achieve the effects of avoiding subsequent processing, low price and high yield

Active Publication Date: 2012-04-11
苏州楚凯药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But, this method uses the iron catalyst of 5mol%~10mol%, can make there is metal residue in the product, and this is very unfavorable for the synthesis of oral medicine, because the removal of metal ion will increase production cost; R 2 Can only be a methyl group, if the requirement is an aryl group, this method is not feasible

Method used

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  • Indole derivative with pyrrolidone structure and preparation method thereof
  • Indole derivative with pyrrolidone structure and preparation method thereof
  • Indole derivative with pyrrolidone structure and preparation method thereof

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preparation example Construction

[0041] The present invention also provides a method for preparing an indole derivative containing a pyrrolidone structure, comprising the following steps:

[0042] The indole compound with the structure of formula (V) and the pyrrolidone compound with the structure of formula (VI) react in an organic solvent under the catalysis of elemental iodine to obtain the indole with the structure of pyrrolidone with the structure of formula (IV) derivative;

[0043]

[0044] Wherein, R is hydrogen, alkyl, alkoxy, nitro, halogen, cyano or methylsulfonyl; R 1 is methyl, ethyl, n-propyl or isopropyl; R 2is hydrogen, alkyl, aryl, nitro, halogen, alkoxy or benzyloxy.

[0045] In the present invention, the indole compound with the structure of formula (V) and the pyrrolidone compound with the structure of formula (VI) are used as raw materials, and elemental iodine is used as the catalyst, and the compound with the structure of formula (IV) can be obtained by one-step reaction in an orga...

Embodiment 1

[0074] In a 25mL round bottom flask, add 0.1056g (0.4mmol) 1-ethoxyl (4-nitrophenyl) methyl) pyrrolidin-2-one, 0.0702g (0.6mmol) indole, 0.0050g (0.02mmol ) iodine and 2mL dichloromethane, stirred and refluxed at 40°C, detected by TLC (thin plate chromatography), and stopped after the disappearance of the raw material 1-ethoxy (4-nitrophenyl) methyl) pyrroline-2-one For the reaction, the reaction product was subjected to column chromatography to obtain 120.6 mg of 1-((1H-indol-3-yl)(4-nitrophenyl)methyl)pyrrolin-2-one with a yield of 90%.

[0075] The 1-((1H-indol-3-yl)(4-nitrophenyl)methyl)pyrroline-2-one is carried out to nuclear magnetic resonance analysis, and the spectrogram data obtained are as follows: 1 H NMR (300MHz, CDCl 3 ): δ=8.36(s, 1H), 8.21(d, J=8.6Hz, 2H), 7.49(d, J=8.6Hz, 2H), 7.42(d, J=8.1Hz, 1H), 7.31-7.22 (m, 3H), 7.11-7.06(t, J=7.5Hz, 1H), 6.97(s, 1H), 6.92(s, 1H), 3.42-3.35(m, 1H), 3.16-3.07(m, 1H ), 2.56-2.45 (m, 2H), 2.09-1.95 (m, 2H) ppm. From the ...

Embodiment 2

[0077] Add 0.1056g (0.4mmol) 1-ethoxy (4-nitrophenyl) methyl) pyrroline-2-one, 0.0787g (0.6mmol) 2-methyl indole, 0.005 g (0.02mmol) iodine and 2mL dichloromethane, stirred and refluxed at 40°C, detected by TLC (thin plate chromatography), the raw material 1-ethoxy (4-nitrophenyl) methyl) pyrroline-2- After the disappearance of the ketone, the reaction was terminated, and the reaction product was subjected to column chromatography to obtain 138 mg of 1-((2-methyl-1 hydrogen-indol-3-yl)(4-nitrophenyl)methyl)pyrroline-2 - Ketone, yield 99%.

[0078] The 1-((2-methyl-1 hydrogen-indol-3-yl) (4-nitrophenyl) methyl) pyrroline-2-one is carried out nuclear magnetic resonance analysis, and the spectrogram data obtained are as follows : 1 H NMR (300MHz, CDCl 3): δ=8.18(d, J=7.6Hz, 2H), 8.09(s, 1H), 7.36(d, J=7.6Hz, 2H), 7.12(s, 1H), 6.94-6.90(m, 3H) , 6.80(s, 1H), 6.78(s, 1H), 3.53-3.48(m, 1H), 3.11-3.06(m, 1H), 2.47-2.45(m, 2H), 2.44(s, 3H), 2.09 -1.95 (m, 2H) ppm. From the above...

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Abstract

The invention provides indole derivatives with a pyrrolidone structure, which have a structure as shown in formula (IV), wherein R is hydrogen, alkyl, alkyloxy, nitro, halogen, cyan or sulfonyl; R2 is hydrogen, alkyl, aryl, nitro, halogen, alkyloxy or benzyloxy. The invention also provides a preparation method of the indole derivatives with a pyrrolidone structure, which comprises the following steps: allowing indole compounds with a structure shown in formula (V) to react with pyrrolidone compounds with a structure shown in formula (VI) with the catalysis of simple substance iodine so as to obtain the indole derivatives with a pyrrolidone structure which have a structure as shown in formula (IV). The invention adopts simple substance iodine as a catalyst, and no metal participates in thereaction process; therefore the obtained product has no metal residues, which thus avoids complicated subsequent processing of the reaction product.

Description

technical field [0001] The invention belongs to the technical field of indole derivatives, in particular to an indole derivative containing a pyrrolidone structure and a preparation method thereof. Background technique [0002] Indole is a compound of pyrrole and benzo in parallel, also known as benzopyrrole, which has the structure of formula (I): [0003] [0004] Indole and its homologues and derivatives are the most common heterocyclic rings in nature, mainly found in natural flower oils, such as jasmine, bitter orange, daffodil, and rosin, etc. Coal tar and feces contain indole or Its homologues and derivatives, urn dyes, tryptophan, alkaloids and auxins are all indole or its homologues and derivatives. Compounds containing indole rings have a wide range of biological activities, such as antifungal, antiviral, antitumor, and anxiolytic effects. Such as vinpocetin with formula (I-a), the drug is not only effective for the prevention and treatment of cerebral arterio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06
Inventor 刘现军纪顺俊姜冉许海燕徐小平
Owner 苏州楚凯药业有限公司
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