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A preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives

A technology of 5-cd and derivatives, applied in organic chemistry and other fields, can solve the problems of difficult preparation of indazine derivatives, complex molecular structure and spatial configuration, etc., and achieve the effect of no by-products and high reaction yield

Active Publication Date: 2020-03-20
TAIYUAN UNIV OF TECH
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Problems solved by technology

[0005] The present invention aims at the problem that the molecular structure and spatial configuration of pyrrolo[2,1,5-cd]indazine derivatives are complex, which leads to the difficulty in the preparation of subsequent pyrrolo[2,1,5-cd]indazine derivatives, and provides A preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives

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  • A preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives
  • A preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives
  • A preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives

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Embodiment Construction

[0030] The present invention is further illustrated by examples.

[0031] The first step, the preparation of intermediate ether derivatives

[0032] (1) Put 416mg of pyrrolo[2,1,5-cd]indazine derivative in a 100mL round bottom flask, add 41mL of dichloromethane to dissolve it, add 300mg of silver perchlorate and 75μL of water to the solution, and stir at room temperature 12h, obtain reaction solution;

[0033] (2) The reaction solution was spin-dried, dissolved in dichloromethane, and purified by column chromatography using petroleum ether: ethyl acetate = 3:1 as the eluent to obtain a white solid product, namely the intermediate ether derivative.

[0034] The obtained intermediate ether derivative was 119 mg, and the yield was 35%.

[0035] Intermediate ether derivatives 1 H NMR, 13 C NMR, HRMS, and IR spectrum data are as follows:

[0036] 1 H NMR (400 MHz, CDCl 3 ): δ 7.56 - 6.80 (m, 20H), 5.25 (d, J = 2.0 Hz,1H), 4.87 (d, J = 3.8 Hz,1H), 4.84 (s, 1H), 4.47 (d, J = 4...

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Abstract

The invention provides a preparation method of a cyclopentyl[f]pyrrolo[2,1,5-cd]indolizine derivative and belongs to the technical field of organic synthesis chemistry, aiming at solving the problemsthat a molecular structure and a spatial configuration of a pyrrolo[2,1,5-cd]indolizine derivative are complicated so that the cyclopentyl[f]pyrrolo[2,1,5-cd]indolizine derivative is difficult to prepare. The cyclopentyl[f]pyrrolo[2,1,5-cd]indolizine derivative is prepared by taking the pyrrolo[2,1,5-cd]indolizine derivative containing iodine atoms and chlorine atoms as a raw material, convertingthe pyrrolo[2,1,5-cd]indolizine derivative into an ether derivative and further treating under a catalysis effect of ruthenium trichloride and silver trifluoromethanesulfonate. According to the preparation method provided by the invention, the cyclopentyl[f]pyrrolo[2,1,5-cd]indolizine derivative is efficiently and stereoselectively through two-step reaction; the reaction yield is high and no byproducts are generated.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and specifically relates to a preparation method of cyclopentyl[f]pyrrolo[2,1,5-cd]indazine derivatives. Background technique [0002] Pyrrolo[2,1,5-cd]indolizine derivatives are a very useful class of compounds. Certain pyrrolo[2,1,5-cd]indolizine derivatives exhibit pharmaceutical activity when bound to estrogen receptors. ((a) Kanstrup, A.; Thorpe, S. M.; Bain, S.; Naerum, L.; Wassermann, K. Bioorg. Med. Chem. Lett. 2000, 10, 399; (b) Jorgensen, A. S.; Jacobsen, P.; Christiansen, L.B.; Bury, P. S.; Kanstrup, A.; Thorpe, S. M.; Naerum, L.; Wassermann, K. Bioorg.Med. Chem. Lett. 2000, 10, 2383.) Some pyrrolo[2, 1,5-cd]indolizine derivatives are efficient fluorescent materials and can be used as light emitters. (Mitsumori, T.; Bendikov, M.; Dautel, O.; Wudl, F.; Shioya, T.; Sato, H.; Sato, Y. J.Am. Chem. Soc. 2004, 126, 16793.Shen, Y. M.; Grampp, G.; Leesakul, N.; Hu, H. W...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 崔培培杨岩
Owner TAIYUAN UNIV OF TECH
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