The structures of organo-selenium compounds are similar to those of organo-sulfur compounds, but they vary drastically in some of their properties. Because of the toxicity and enormously unpleasant odor of organo-selenium compounds, they have not been as well explored as could be justified. For example, organo-selenium compounds are reported as active antibacterial, antiviral, antifungal, anti-parastitic, anti-inflammatory and antihistamine agents. Recently, Liotta and his co-workers reported the use of phenyl selenide anion as the key reagent for the conversion of lactones to x-vinylcarboxylic acids. The choice of phenyl selenide anion as the ring-opening reagent seemed attractive for two reasons. First, a simple lactone possesses two sites which are potentially reactive to nucleophiles, the carbonyl carbon and the carbinolic carbon. Based on hard-soft acid-base theory, a soft nucleophile, such as phenyl selenide anion, should exhibit a preference for SN2-type attack at the carbinolic carbon and thus generate x-vinylcarboxylic acids. An ample variety of aromatic acids have been used as key intermediates for the synthesis of 1,3,4-oxadiazole rings, which occupy a key place in medicinal chemistry due to their significant biological properties, including antimicrobial, antituberculosis and anticancer activity. It is well-known that the combination of two or more types of heterocycles into one molecule may provide increased bioactivities due to the structural synergistic effect. The synthesis of 1,3,4-oxadiazoles bearing selenium requires aromatic acids containing selenium. These acids are difficult to synthesize. In the course of our current research, we developed a new process for the preparation of an aromatic acid containing selenium, namely 2-[(methylselenyl)methyl]benzoic acid, by the SN2type cleavage of 2-benzofuran-1(3H)-one with methyl selenide anion generated from dimethyl diselenide. We observed good yield and purity. Only two methods are reported for the synthesis of 2-[(methylselenyl)methyl]benzoic acid. But both the methods involved multistep protocols with expensive starting

中文翻译：

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一种简便实用的一锅法合成 2-[(甲基硒基)甲基]苯甲酸

有机硒化合物的结构与有机硫化合物的结构相似，但它们的某些性质差异很大。由于有机硒化合物的毒性和极其令人不快的气味，它们没有得到充分的探索。例如，有机硒化合物被报道为活性抗菌剂、抗病毒剂、抗真菌剂、抗寄生虫剂、抗炎剂和抗组胺剂。最近，Liotta 和他的同事报道了使用苯基硒阴离子作为将内酯转化为 x-乙烯基羧酸的关键试剂。选择苯基硒阴离子作为开环试剂似乎很有吸引力，原因有二。首先，简单的内酯具有两个可能与亲核试剂反应的位点，羰基碳和甲醇碳。基于硬-软酸碱理论，软亲核试剂，如苯基硒化物阴离子，应该表现出对甲醇碳的 SN2 型攻击的偏好，从而生成 x-乙烯基羧酸。多种芳香酸已被用作合成 1,3,4-恶二唑环的关键中间体，由于其显着的生物学特性，包括抗菌、抗结核和抗癌活性，它们在药物化学中占有重要地位。众所周知，由于结构协同效应，将两种或多种杂环组合成一个分子可以提供增加的生物活性。合成含硒的 1,3,4-恶二唑需要含硒的芳香酸。这些酸很难合成。在我们目前的研究过程中，我们开发了一种制备含硒芳香酸的新工艺，即 2-[(甲基硒基)甲基]苯甲酸，通过 2-苯并呋喃-1(3H)-one 与由二甲基二硒化物产生的甲基硒阴离子进行 SN2 型裂解. 我们观察到良好的产率和纯度。仅报道了两种合成 2-[(甲基硒基)甲基]苯甲酸的方法。但是这两种方法都涉及多步协议，启动成本高