One-pot cascade trifluoromethylation/cyclization of imides: synthesis of α-trifluoromethylated amine derivatives.
Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the α-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.
Department of Chemistry, Indian Institute of Technology Madras , Chennai - 600036, India.
Vinay Kumar
VK
Pandey
Pazhamalai
P
Anbarasan
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007094:Imides / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure
D000588:Amines; D007094:Imides