25370-96-1Relevant academic research and scientific papers
Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles
Paudyal, Mahesh P.,Wang, Mingliang,Siitonen, Juha H.,Hu, Yimin,Yousufuddin, Muhammed,Shen, Hong C.,Falck, John R.,Kürti, László
supporting information, p. 557 - 560 (2021/02/06)
A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va
Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination
Falk, Eric,Gasser, Valentina C. M.,Morandi, Bill
, p. 1422 - 1426 (2021/03/08)
We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.
Direct α-oxytosylation of carbonyl compounds: One-pot synthesis of heterocycles
John, Oliver R. S.,Killeen, Niall M.,Knowles, Deborah A.,Yau, Sze Chak,Bagley, Mark C.,Tomkinson, Nicholas C. O.
, p. 4009 - 4012 (2008/02/11)
N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct α-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.
O-Arenesulfonyl-N-alkylhydroxylamines as Aminating Reagents
Tamura, Yasumitsu,Ikeda, Hiroyuki,Morita, Iwao,Tsubouchi, Hidetsugu,Ikeda, Masazumi
, p. 1221 - 1224 (2007/10/02)
O-(p-Toluenesulfonyl)-N-methyl-, -N-ethyl-, and -N-isopropil-hydroxylamines and O-mesitylenesulfonyl-N-methylhydroxylamine were prepared.The N-methyl and N-ethyl derivatives were found to react with tertiary amines and triphenylphosphine to give the corresponding N-(alkylamino)ammonium salts and P-(alkylamino)phosphonium salts, but the N-isopropyl derivative was less reactive, probably due to steric effects.These reagents also reacted with tri-n-butylborane to give the corresponding alkyl-n-butylamines.Keywords-- electrophilic aminating reagent; tert-butoxycarbonylation; di-tert-butyl dicarbonate; N-(methylamino)ammonium salts; P-(methylamino)triphenylphosphonium salt; N-(methylamino)pyridinium salt; secondary amines
