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US 2022/0169623 A1Published application
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.
Claims12
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=0, 1, or 2;
- where R1, R2 and R3 represent substituent groups on a connected ring, which are independently selected from the groups consisting of hydrogen group, C1-20 alkyl group, C6-20 aryl group, C3-20 cycloalkyl group, and C6-20 aryl-group-C1-20 alkyl-group;
- or adjacent two of which being R1/R2, R2/R2, R2/R3 or R1/R3 substituent groups are connected to each other and form one of saturated or unsaturated five to seven membered carbon rings together with carbon atoms connecting the adjacent two substituent groups;
- wherein the organic solvent is one selected from alcoholic solvents.
6 more elements
Dependencies are inferred from the claim text.