184157-16-2

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 184157-07-1 6-Trifluoromethyl-3,4-dihydro-1H-pyridin-2-one 
• 1027194-65-5 6,6,6-Trifluoro-5-oxo-hexanoyl chloride 
• 184157-09-3 6,6,6-trifluoro-5-oxohexanoic acid 

Relevant academic research and scientific papers

Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones

Staudinger/aza-Wittig reaction of 6,6,6-trifluoro-5-oxohexanoyl azide with PPha or PBua was examined. A reactive intermediate acyl imine 1 was trapped by methanol. Without nucleophile, isomerized enamide form 3 was obtained. W-Iodobenzoylation and 2V-haloalkylation of 3 and following radical cyclization via the 5-exo or 6-exo mode gave benzoindolizidinone, indolizidinone, and quinolizidinone derivatives 10-14, which have a trifluoromethyl group at the bridgehead position adjacent to nitrogen. Although LiAlH4 reduction of 10 and 11 gave a mixture of saturated benzoindolizidine 15 and amino alcohol 16, reduction with BH3/THF selectively gave the desired 15 and indolizidine 17 from 13.