University of Vienna, Department of Pharmaceutical Chemistry, Althanstrasse, 14, 1090 Vienna, Austria.
Org Biomol Chem. 2019 Feb 13;17(7):1970-1978. doi: 10.1039/c8ob02312c.
Thioformamides are easily prepared - under full chemocontrol - through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.
硫代甲酰胺可通过原位生成的施瓦茨试剂对异硫氰酸酯进行部分还原来轻松制备 - 完全化学控制。起始材料的高亲电性使得氢化物离子的加成变得简单，从而为获得各种官能化的硫代甲酰胺提供了可靠且高产的方法。对还原条件敏感的化学基团，如硝基、酯、烯烃、偶氮、叠氮和酮基，不会干扰该过程的化学选择性。此外，起始材料中所包含的立体化学信息在最终产物中得到完全保留。还简要讨论了所选硫代甲酰胺模板的合成潜力。
