Electrochemical Oxidation of 2-Substituted 3-N-(Arylamino)-4,4,4-trifluoro-2-butenoate. An Access to 3-Substituted 2-(Trifluoromethyl)-3H-indoles

Trifluoroacetimidoyl halides: a potent synthetic origin

“…Uneyama and co-workers developed an electrochemical oxidation of 2-substituted 3-(N-arylamino)-4,4,4-trifluoro-2butenoate for the production of 2-(trifluoromethyl)-indoles (Scheme 61). 79 The butanoate derivatives 61-A could be readily prepared by the nucleophilic reaction of active methylene compounds with trifluoroacetimidoyl chlorides. The 61-A underwent a sequential reaction of single-electron-oxidation, deprotonation, a further single-electron-oxidation, addition of water and demethoxylation process to afford the p-benzoquinone imines 61-B.…”

Iodine-Mediated Synthesis of 3H-Indoles via Intramolecular Cyclization of Enamines

“…3 H -Indole is one of the most important structural units found in nature and has been utilized as a key scaffold to construct various indoline alkaloids . Although there are a variety of methods to synthesize 1 H -indole derivatives, the methodologies for the synthesis of 3 H -indole derivatives are very limited . Therefore, a general and efficient method for the synthesis of 3 H -indole derivatives is an attractive and formidable challenge in synthetic chemistry …”

Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel–Crafts Reaction

“…13 Trifluoroacetimidoyl chlorides were described for the first time in 1994 and were applied in the electrochemically performed synthesis of 2-(trifluoromethyl)-3H-indole derivatives. 14 In recent decades, research efforts on trifluoroacetimidoyl chlorides have led to the synthesis of different trifluoromethylated heterocycles. [15][16][17] Earlier, we have reported the synthesis of trifluoromethylated tetrazoles and pyrroles by using trifluoroacetimidoyl chlorides.…”