35876-70-1Relevant articles and documents
Synthesis method for preparing benzoxazole compound from catechol compound and amine compound
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Paragraph 0078-0080, (2021/08/19)
The invention provides a method for preparing a benzoxazole compound from a catechol compound and an amine compound. The method has the characteristics of cheap and easily available raw materials, wide substrate range, simple reaction system, easy separation of the obtained target product, simple reaction operation, safety, reliability and the like. Compared with a transition metal catalyzed synthesis method, the system does not need expensive metal catalysts and ligands, so that the economic cost is reduced, and the problems of environmental pollution caused by heavy metals and metal residues in products are avoided. The reaction functional group has higher tolerance, can be used for synthesizing a series of 2-aryl, trifluoromethyl, ester group, halogen, 2-alkenyl, 2-alkynyl and 2-alkyl substituted benzoxazole derivatives, can be used for benzoxazole compounds containing various special functional group structures, and has higher application value.
One-pot multicomponent reaction of catechols, ammonium acetate, and aldehydes for the synthesis of benzoxazole derivatives using the fe(iii)-salen complex
Sharghi, Hashem,Aboonajmi, Jasem,Aberi, Mahdi
, p. 6567 - 6577 (2020/06/08)
The Fe(III)-salen complex has been applied successfully as a catalyst for the novel, simple, efficient, and one-pot multicomponent synthesis of benzoxazole derivatives from catechols, ammonium acetate as the nitrogen source, and aldehydes (nontoxic and cheap alternatives of amines) for the first time. Using this procedure, a wide range of benzoxazoles was successfully synthesized in the presence of a catalyst in EtOH under mild conditions, and all products were obtained in excellent yields. To the best of our knowledge, this method is the first example of the multicomponent synthesis of benzoxazole derivatives using these starting materials. The notable features such as the use of air that is considered as a benign oxidant and EtOH as a green solvent, ease of product separation, readily available and inexpensive aldehydes, and mild conditions make our procedure more efficient and practical for organic synthesis. Moreover, the current protocol is successfully applied to synthesize desirable products on a large scale.
Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols
Oshimoto, Kohei,Tsuji, Hiroaki,Kawatsura, Motoi
, p. 4225 - 4229 (2019/05/10)
We describe herein the synthetic method to benzoxazole derivatives via the copper-catalyzed hydroamination of alkynones with 2-aminophenols. The method produced a wide variety of functionalized benzoxazole derivatives in good yields. Preliminary mechanistic experiments revealed that the reaction would proceed through the copper-catalyzed hydroamination of alkynones and the sequential intramolecular cyclization of β-iminoketones/elimination of acetophenone promoted by the copper catalyst.