Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction

Synlett DOI: 10.1055/s-0043-1763751 Herein, we report the novel strategy for the synthesis of 4-enamino-5-phenyl-2,3-dihydroisothiazole 1-oxides (in other words α-phenyl β-enamino γ-sultims) based on the CSIC reaction. Particularly, readily available α-amino nitriles (the Strecker products) reacted with benzyl sulfinyl chloride to give the corresponding sulfinamides, which upon treatment with excess of LiHMDS converted into the target α-phenyl β-enamino γ-sultims. The method works well and tolerates strained 3- and 4-membered spirocyclic substituents. A preliminary in silico study indicated that the γ-sultim scaffold can be considered a promising pharmacophore template. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  open access Full text

Source: Synlett - April 15, 2024 Category: Chemistry Authors: Chuchvera, Yaroslav O. Tararina, Valentyna Chuchvera, Inna Ostapchuk, Eugeniy N. Popova, Maria V. Shishkina, Svitlana V. Volovenko, Yulian M. Dobrydnev, Alexey V. Tags: letter Source Type: research