Tiwari Shubham, Chandrashekharappa Sandeep, Gururaja Guddeangadi N
School of Chemical Sciences, Central University of Gujarat, Gandhinagar 382030, India.
Department of Medicinal Chemistry, NIPER-R, Lucknow 226002, India.
Org Biomol Chem. 2023 Nov 1;21(42):8563-8572. doi: 10.1039/d3ob01416a.
A mild, catalyst and oxidant-free efficient protocol for synthesizing α-ketothioamides is reported with a broad substrate scope. The presented protocol demonstrates the confined reactivity of amines. The polysulfide derived from elemental sulfur and amines in an aqueous medium drives the pathway toward diverse α-ketothioamides over thioamides. Substrates with different substituent groups were compatible with the presented protocol, and the respective ketothioamides were separated in good to excellent yields. The ketothioamides, known to exhibit anti-cancer properties, were synthesized by the proposed protocol. Furthermore, the synthetic utility was explored with the typical synthesis of ketoamides.
报道了一种温和、无催化剂和氧化剂的高效合成α-酮硫酰胺的方法，该方法具有广泛的底物范围。所提出的方法证明了胺的受限反应性。在水性介质中由元素硫和胺衍生的多硫化物驱动生成多种α-酮硫酰胺而非硫酰胺的反应途径。具有不同取代基的底物与所提出的方法兼容，相应的酮硫酰胺以良好至优异的产率分离出来。已知具有抗癌特性的酮硫酰胺通过所提出的方法合成。此外，还通过典型的酮酰胺合成对该合成方法的实用性进行了探索。
