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Polycyclic heterocyclic compound synthesized with water as medium, preparation method and application thereof

A technology of heterocycles and compounds, applied in the field of chemical synthesis, to achieve the effects of environmental friendliness, good compatibility, and easy-to-obtain raw material synthesis

Active Publication Date: 2021-06-04
遵义医药高等专科学校
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the possibility of electron-deficient nitroheteroaromatics as substrates participating in aqueous reactions remains to be explored

Method used

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  • Polycyclic heterocyclic compound synthesized with water as medium, preparation method and application thereof
  • Polycyclic heterocyclic compound synthesized with water as medium, preparation method and application thereof
  • Polycyclic heterocyclic compound synthesized with water as medium, preparation method and application thereof

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Embodiment 1

[0032] In the reaction tube, add benzo six-membered ring dicyanoalkene 1a (0.10mmol), 2-nitrobenzofuran 2a (0.12mmol) successively, add Cs 2 CO 3 (1eq, 0.1mmol), hexadecyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL water, stirred at room temperature for 24h, TLC detected that the basic reaction was complete, and the reaction solution was filtered to obtain a filter cake. After dissolving dichloromethane, the sample was purified by column chromatography (eluent: V (petroleum ether): V (ethyl acetate) = 5:1) to obtain compound 4aa, a white solid, melting point: 182.3-183.1 °C; yield 90%. NMR (such as figure 1 and 2 Shown) and results such as high-resolution mass spectrometry test are as follows: 1 HNMR (300MHz, DMSO-d6) δ8.20(d, J=7.7Hz, 1H), 8.07(d, J=7.5Hz, 1H), 7.75(d, J=8.3Hz, 1H), 7.60(t, J=7.8Hz,1H),7.49-7.41(m,1H),7.41-7.29(m,3H),6.36(s,2H),3.17-3.06(m,2H),2.89-2.78(m,2H) ; 13 C NMR (75MHz, DMSO-d6) δ156.2, 142.0, 138.5, 138.0, 132.1, 131.2, 128.5,...

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Abstract

The invention discloses a class of polycyclic heterocyclic compounds synthesized with water as a medium, which belongs to the technical field of chemical synthesis and has a structure as shown in the general formula (I): (I) In the general formula (I), X is selected from O, S, N-R, Y is selected from H, CH 2 , OCH 2 , (CH 2 ) 2 , (CH 2 ) 3 , Ar is selected from alkyl or halogen or aryl substituted benzene ring, furan ring, thiophene ring, R 1 Selected from H, alkyl, halogen, aryl; the present invention uses various substituted dicyanoalkene synthons and various substituted 2-nitroheteroarenes or 3-nitroheteroarenes as raw materials, in water as medium Alkali-promoted [4+2] alkenyl cyclization reaction occurs under certain conditions; this type of compound has important application value for the screening of drugs and the pharmaceutical industry; and the application in photoluminescent materials is also of great value; the operation of the present invention It is simple and easy to operate, the raw materials are cheap and easy to obtain, and it is carried out under the condition of water as the medium, which is friendly to the environment, has good air stability, wide applicability, and has good compatibility with various substituents.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a class of polycyclic heterocyclic compounds synthesized using water as a medium, a preparation method and application thereof. Background technique [0002] As we all know, water resources in nature are abundant, environmentally friendly and inexpensive. However, the poor solubility of most organic compounds in water limits their application in organic synthesis. Organic reactions in aqueous media have gained widespread attention since the concept of green chemistry was proposed. [0003] (1) Dibenzofuran, dibenzopyran, and dibenzopyrrole skeletons are widely found in many natural products and drugs with important biological activities, and exhibit anticancer, antibacterial, antimalarial, antiallergic and antiallergic effects. The inflammatory activity makes its synthesis have potential application prospects. (2) Electron-deficient nitroheteroaromatic compounds suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/77C07D307/91C07D333/76C07D333/50C07D495/04C07D333/78C07D333/80C09K11/06
CPCC07D307/77C07D307/91C07D333/50C07D333/76C07D333/78C07D333/80C07D495/04C09K11/06C09K2211/1088C09K2211/1092
Inventor 卓俊睿袁伟成赵建强全保学杜安妮王可可
Owner 遵义医药高等专科学校
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