Synthesis method of selenium-containing isochroman compound

Abstract

The invention discloses a synthesis method of a selenium-containing isochroman compound. The synthesis method comprises the following steps: under the protection of nitrogen, adding N-phenylseleno saccharin (NPSSac) into a reactor, then adding dichloromethane to completely dissolve the N-phenylseleno saccharin, adding a 1-[(cinnamoxy) methyl]-3, 4, 5-trimethoxy benzene compound and boron trifluoride diethyl etherate after the N-phenylseleno saccharin is completely dissolved, stirring at 20-60 DEG C for 2-6 hours until the reaction is complete, and after the reaction is finished, quenching, extracting, combining organic phases, drying, concentrating, separating and purifying to obtain the selenium-containing isochroman compound. The synthesis method disclosed by the invention is relatively easy to operate, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a selenium-containing isochroman compound. Background technique [0002] Isochroman belongs to the heterocyclic compound of isobenzopyran. The levobacterium citrinin that was first discovered was a compound with isochroman structure. They were isolated from bacteria such as Aspergillus terreus and Aspergillus candida. of. With the passage of time, scientists engaged in phytochemical separation have discovered that many natural products have the structure of heterochroman. Therefore, the synthesis of compounds with the isochroman structure has also aroused great interest of chemists, and the synthesis of such compounds has been deeply studied. Since Normant carried out the artificial synthesis of isochroman rings, scientists have just The chroman changed the structure of the parent ring to find compounds with good drug activity. Later, the bio...

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Problems solved by technology

[0004] However, as can be seen from the above, initially by β-phenylethyl alcohol and paraformaldehyde as reaction substrates, hydrogen chloride is used to catalyze the synthesis of isochroman compounds. This method has defects such as serious environmental pollution, low yield and long reaction time. Later, In succession, zinc trichloride and p-toluenesulfonic acid were used instead of hydrogen chloride to catalyze, thereby reducing environmental pollution.

With the development of science, there have been many routes for synthesizing isochromans, but there are no reports on the use of organoselenium reagents to participate in the reaction to form carbon-carbon bonds to synthesize isochromans.