Synthesis method of isocoumarin compounds

A technology of isocoumarin and synthesis method, applied in chemical recovery, organic chemistry, etc.

Inactive Publication Date: 2019-06-21
XIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After painstaking research, the inventor proposes a novel method for preparing isocoumarin compounds using benzaldehyde as a weakly chelating carboxyl precursor in the present invention. As far as the inventor knows, such a method has not yet been seen in the prior art to report

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  • Synthesis method of isocoumarin compounds
  • Synthesis method of isocoumarin compounds
  • Synthesis method of isocoumarin compounds

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Experimental program
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Effect test

Embodiment 1-15

[0041] Embodiment 1-15 reaction condition optimization test

[0042] Using benzaldehyde shown in formula I-1 and diphenylacetylene shown in formula II-1 as templates, the influence of different reaction conditions on the optimization results of the synthesis process was discussed, and representative examples 1-15 were selected. . The results are shown in Table 1.

[0043]

[0044] Wherein the typical test operation of embodiment 1 is as follows:

[0045] In the 25mL Schlenk lock reactor, add benzaldehyde (0.6mmol) shown in formula I-1, diphenylacetylene (0.3mmol) shown in formula II, Cp*Co(CO)I successively 2 (10mol%), copper oxide (2equiv), molecular sieve (100mg), and then add PEG-400 (2g), under oxygen atmosphere (1atm), the oil bath is heated to 100 ℃, after the insulation reaction for 24 hours, by TLC or GC -MS detects that the reaction raw materials are completely consumed. After the reaction was complete, cool to room temperature, extract with diethyl ether (3×10...

Embodiment 34

[0059] Embodiment 34 Catalyst recycling test

[0060] Extracted with ether in Example 1 containing PEG-400, Cp*Co(CO)I 2 , the mixture of CuO and molecular sieves was concentrated in vacuo, added to the Schlenk reactor of 25 mL, and then added successively benzaldehyde (0.6 mmol) shown in formula I-1, diphenylacetylene (0.3 mmol) shown in formula II ), under an oxygen atmosphere (1atm), the oil bath was heated to 100° C., and after 24 hours of insulation reaction, the reaction raw materials were completely consumed by TLC or GC-MS detection. After the reaction was complete, cool to room temperature, extract with diethyl ether (3×10 mL), combine the diethyl ether phases and wash with saturated brine, anhydrous Na 2 SO 4 Dry and concentrate in vacuo to give a residue. Then, the residue was separated by silica gel column chromatography (the elution phase was n-hexane / ethyl acetate) to obtain isocoumarin compounds represented by formula III-1. Yield 82%. The distribution of r...

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Abstract

The invention discloses a synthesis method of isocoumarin compounds. According to the method, benzaldehyde compounds and alkyne compounds are taken as reaction materials, and the isocoumarin compoundsare prepared under the condition of a cobalt catalyst with PEG-400 as a reaction medium. The method has the advantages that the catalysis conditions are novel, the catalyst cost is low, the catalystand the reaction medium PEG-400 can be recycled, the application range of a reaction substrate is wide, the yield is high, and the method is environmentally friendly.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, in particular to a method for synthesizing isocoumarin compounds. Background technique [0002] Isocoumarins are a very important class of O-heterocyclic compounds, which widely exist in various natural products and medicines. Therefore, great attention has been paid to the development of novel, economically viable synthetic strategies for isocoumarinoids. Among these synthetic approaches, the cyclization of unsaturated hydrocarbons (including alkynes and alkenes) via weakly chelating-assisted C–H bond functionalization has shown particular appeal due to its high atom economy and facile process routes. Typically, these transformations have focused on the transition metal-catalyzed cyclization of aromatic acids and their derivatives with alkynes, where the carboxyl group acts as a weak chelating group to selectively functionalize its ortho C(sp2)–H bond, thereby Prepare isocoumarin (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/76C07D409/14
CPCY02P20/584
Inventor 陶李明李传华陈俊刘卉欧佳
Owner XIANGNAN UNIV
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