107616-24-0Relevant academic research and scientific papers
Copper-promoted sandmeyer trifluoromethylation reaction
Dai, Jian-Jun,Fang, Chi,Xiao, Bin,Yi, Jun,Xu, Jun,Liu, Zhao-Jing,Lu, Xi,Liu, Lei,Fu, Yao
, p. 8436 - 8439 (2013/07/19)
A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.
Dihydrobenzoxazines and Tetrahydroquinoxalines by a Tandem Reduction-Reductive Amination Reaction
Bunce, Richard A.,Herron, Derrick M.,Hale, Lu Y.
, p. 1031 - 1039 (2007/10/03)
A tandem reduction-reductive amination reaction has been applied to the synthesis of 3,4-dihydro-2H-1,4-benzoxazines and 1-acetyl-1,2,3,4-tetrahydroquinoxalines. The nitroketones required for the benzoxazine ring closures were prepared by (A) alkylation of the anion derived from 2-nitrophenol with an allylic halide or (B) nucleophilic aromatic substitution of an allylic alkoxide on 2-fluoro-1-nitrobenzene followed by ozonolysis. Precursors for the quinoxalines were prepared by alkylation of the anion of 2-nitroacetanilide with an allylic halide followed by ozonolysis. Catalytic hydrogenation of the nitroketones using 5% palladium-on-carbon in methanol then gave the target heterocycles by a reduction-reductive amination sequence. The N-methyl derivatives for both ring systems were easily prepared by adding 5-10 equivalents of aqueous formaldehyde prior to the reduction. The dihydrobenzoxazines were isolated in high yield following purification by chromatographic methods; tetrahydroquinoxalines were isolated in a similar manner and possessed differentiated functionality on the two nitrogens.
Synthesis of functionalised indolines by radical-polar crossover reactions
Murphy, John A.,Rasheed, Faiza,Gastaldi, Stephane,Ravishanker,Lewis, Norman
, p. 1549 - 1558 (2007/10/03)
Functionalised indolines have been prepared by treating tetrathiafulvalene (TTF) with 2-(N-acyl-N-allylamino)benzenediazonium tetrafluoroborates. N-Benzoyl-protected substrates afford complex reaction mixtures due to competing radical cyclisation onto the benzoyl group. Acetamides react more efficiently affording good yields of product alcohols when the reactions are carried out in moist acetone.
Iododediazoniation of Arenediazonium Salts Accompanied by Aryl Radical Ring Closure
Beckwith, Athelstan L. J.,Meijs, Gordon F.
, p. 1922 - 1930 (2007/10/02)
Treatment of o-(allyloxy)benzenediazonium tetrafluoroborate (1a) with sodium iodide in acetone affords the cyclized iodide 2a in good yield by a mechanism involving the generation and exo cyclization of the aryl radical 6a.Other diazonium salts (1b-i) containing suitable unsaturated side chains behave similarly, but those (1l,1m) in which there is an N-allylsulfonamido group yield mainly products formed by endo cyclization.The diazonium salts 1j and 1k do not give cyclized products.Factors affecting the mechanism, rates, and regiochemistry of the reaction are discussed.
