60721-36-0Relevant academic research and scientific papers
β,β,β-Trichloroethyl-NH-Enamine as Viable System for 5-Endo-trig Radical Cyclization via Multifaceted CuI?CuII Redox Catalysis: Single Step Synthesis of Multi-Functionalized NH-Pyrroles
Ram, Ram N.,Sadanandan, Sandhya,Kumar Gupta, Dharmendra
supporting information, p. 5661 - 5676 (2019/11/16)
Here we report a mild and regioselective copper-catalyzed direct synthesis of multi-substituted and functionalized NH-pyrroles in high yields from diverse β,β,β-trichloroethyl-NH-enamines via a novel 5-endo-trig radical cyclization mode, previously known to be unviable in the enamine system. An approach to transform a geometrically ‘disfavored to favored’ 5-endo-trig radical cyclization mode in NH-enamine systems via multifaceted CuI?CuII redox catalysis generating radicals, preventing dehalogenative reduction of radical precursors and dehydrohalogenating the 5-endo-trig cyclized products have been demonstrated experimentally. With wider substrate scope, this method incorporates halo-, NH- and carbonyl functionalities besides alkyl, aryl and heteroaryl substituents in the pyrrole unit easily. These difficult to prepare 3-halo-NH-pyrroles are potential sources for natural products, agrochemicals, pharmaceuticals and organometallic chemistry.
N-(2,2,2-trichloroethylidene)- and N-(1-hydroxy-2,2,2-trichloroethyl) amides in C-amidoalkylation reaction of functionally-substituted aromatic compounds
Aizina,Rozentsweig,Levkovskaya,Rozentsweig,Mirskova
, p. 235 - 238 (2007/10/03)
A reaction with phenol and pyrocatechol of N-(2,2,2-trichloroethylidene)arenesulfonyl-, ethoxycarbonylamides and 1-hydroxy-substituted N-(2,2,2-trichloroethyl)amides of arenesulfonic, carbamic, and acetic acids in the presence of oleum or in sulfuric acid provided the corresponding (1-amido-2,2,2-trichloroethyl)-substituted phenols. N-(2,2,2-Trichloroethylidene)-4-chlorobenzenesulfonamide reacted with salicylamide in the presence of oleum to afford 3-aminocarbonyl-4-[2,2,2-trichloro-1-(4-chlorobenzene-sulfonamido)ethyl]benzene whereas the 1-hydroxy-2,2,2-trichloroethylamides of the acetic, carbamic, and arenesulfonic acids did not enter into such reactions.
N-(1-ARYL-2,2,2-TRIHALOGENOETHYL)CARBOXAMIDES
Bal'on, Ya. G.,Smirnov, V. A.
, p. 2051 - 2054 (2007/10/02)
The readily obtained products from the condensation of trihalogenoacetaldehydes with carboxamides react with benzene and its homologs in the presence of concentrated sulfuric acid with the formation of N-(1-aryl-2,2,2-trihalogenoethyl)carboxamides.The latter were used for the production of 1-aryl-2,2,2-trihalogenoethylamines and 1-acylimino-1-aryl-2,2,2-trihalogenoethanes.
