86194-06-1Relevant academic research and scientific papers
Indolizines. 3. Oxidation Products of Indolizinols: Radicals, Ions, and Oxidized Dimers
Wadsworth, Donald H.,Weidner, Charles H.,Bender, Steven L.,Nuttall, Robert H.,Luss, Henry R.
, p. 3652 - 3660 (2007/10/02)
The oxidation products of 1- and 3-indolizinols have been investigated and characterized.A variety of stabilized indolizinols form stable, crystalline free radicals by one-electron oxidations.Both 7-H and 7-CH3 substituted indolizinols, when subjected to the exhaustive aerial or benzoquinone oxidation, from the oxidatively coupled 1,1'- or 3,3'-dioxo-7,7'-bisindolizines.Two-electron oxidation of indolizinols formed oxoindolizinium ions.
Enamines from Iodine Oxidation of Trialkylamines. 1. Electrophilic Capture by Cationic Heterocyclic Rings
Wadsworth, Donald H.,Detty, Michael R.,Murray, Bruce J.,Weidner, Charles H.,Haley, Neil F.
, p. 2676 - 2681 (2007/10/02)
Simple enamines derived from acetaldehyde, acetone, and propionaldehyde were generated in situ by iodine oxidation of triethylamine, N,N-diisopropylmethylamine, and tri-n-propylamine, respectively.The enamines were captured by a variety of cationic substrates including trityl, indolizinium, dithiolium, pyrylium, thiapyrylium, selenapyrylium, and tellapyrylium cations.The use of a second equivalent of iodine (or excess) oxidized the initial products of enamine capture to various iminium dyes.These dyes were easily hydrolyzed to heterocyclylidene aldehydes and ketones.Cyclic amines such as N-methylpyrrolidine gave enamines derived from ring oxidation. 2-Cyano-N,N-dimethylethylamine generated a cyano-substituted enamine under the reaction conditions.
