One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene.
Kamil ŚwiątekGreta Utecht-JarzyńskaMarcin PalusiakJun-An MaMarcin JasińskiPublished in: Organic letters (2023)
A synthetically useful approach for one-pot preparation of 1-aryl-3-trifluoromethylpyrazoles using in situ generated nitrile imines and mercaptoacetaldehyde applied as 1 equiv of acetylene is presented. This protocol comprises (3 + 3)-annulation of the mentioned reagents to form 5,6-dihydro-5-hydroxy-4 H -1,3,4-thiadiazine, followed by cascade dehydration/ring contraction reactions with p -TsCl. In addition, representative nonfluorinated analogues functionalized with Ph, Ac, and CO 2 Et groups at the C(3)-position of the pyrazole ring were also prepared by the devised method.