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US 11,548,862 B2Granted
Preparation method of selenium-containing heterocyclic compounds
AssigneeWenzhou University
InventorsMiaochang Liu, Liguo Lu, Chuanli Chen, Yunbing Zhou, Huayue Wu
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Abstract
A reaction of azacyclopropane derivative with elemental selenium and TMSCN to construct a selenium-containing heterocycle under metal-free and additive-free conditions is provided. The new strategy features no metal participation, no additive promotion, a wide substrate selection range and a good functional group compatibility, and provides an efficient and green approach to constructing a variety of selenium-containing heterocyclic compounds in a highly concise way.
Claims10
A preparation method of a selenium-containing heterocyclic compound, comprising the following steps:
- sequentially adding azacyclopropane derivative of formula I, selenium powder, trimethylsilyl cyanide (TMSCN) and an organic solvent to a reactor equipped with a magnetic stirrer,
- subsequently replacing atmosphere in the reactor with an inert atmosphere, heating and stirring for reaction to obtain a reaction mixture,
- diluting the reaction mixture with ethyl acetate after the reaction, and then filtering through a silica gel pad to obtain a filtrate,
- concentrating the filtrate under a reduced pressure to obtain a residue, and then purifying the residue by silica flash chromatography, thereby obtaining a selenium-containing heterocyclic compound of formula II;
- wherein a formula for the reaction is as follows:
- where n=2;
- where adjacent two R1/R2 substituent groups are connected to each other and form a benzene ring structure together with carbon atoms connecting the adjacent two R1/R2 substituent groups, and adjacent two R2/R3 substituent groups each are hydrogen group;
- wherein the organic solvent is one selected from alcoholic solvents.
5 more elements
Dependencies are inferred from the claim text.