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Regio- and stereo-selective ring expansion of keto-aziridines to the corresponding thiomorpholines
Published in Journal of Sulfur Chemistry, 2021
Fatemeh Khodadadi, Heshmat Allah Samimi, Jalal Albadi, Ahmadreza Momeni
The earliest example of the synthesis of a 3-oxothiomporpholine and thiomorpholines were described by Karrer and Bestian respectively [1]. The 3-thiomorpholinone skeleton plays a significant role for biological activity, such as enhancement of brain noradrenaline and dopamine turnover [2], hypnotic activity [3], and antagonism on 5-HT1b [4], and EP4 receptors [5]. Thiomorpholines have also been found to exhibit antihypertensive [6] and antimycobacterial activities [7] as well as in the 1,4-benzothiazine calcium antagonist Semotiadil [8–10], pyrimidothiazine derivatives [11]. In addition, chiral thiomorpholines have been used as a chiral catalyst for sulfur ylide mediated symmetric epoxidation of aldehydes [12].