121998-66-1Relevant academic research and scientific papers
ACCESS TO AMINOPHENYLCARBENES VIA DIAZIRINE EXCHANGE REACTIONS
Moss, Robert A.,Cox, D. Phillip,Tomioka, Hideo
, p. 1023 - 1026 (1984)
Phenylbromodiazirine (1) reacts with a variety of primary and secondary amines affording a series of aminophenylcarbenes.
Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
Borys, Andryj M.,Gil-Negrete, Jose M.,Hevia, Eva
supporting information, p. 8905 - 8908 (2021/09/10)
Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.
Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives
Sakai, Norio,Hori, Hiroaki,Yoshida, Yoshihiro,Konakahara, Takeo,Ogiwara, Yohei
, p. 4722 - 4729 (2015/07/27)
We demonstrated a copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals leading to the synthesis of α-aryl glycines and diarylmethylamines. Under an ambient atmosphere, this catalytic system could be applied to the activation of a C(sp3)-O bond of N,O-acetals with an ester and an aryl group, or without a coordinating substituent, as well as to a C(sp3)-N bond of N,N-aminals.
Electrooxidative cyclization of hydroxyamino compounds possessing a benzyl group
Okimoto, Mitsuhiro,Ohashi, Kousuke,Yamamori, Haruki,Nishikawa, Shinnosuke,Hoshi, Masayuki,Yoshida, Takashi
experimental part, p. 1315 - 1322 (2012/06/30)
Several novel 2-aryl-1,3-oxazinane and 2-aryl-1,3-oxazolidine derivatives were synthesized from N-benzyl-2-piperidineethanols and N-benzyl-2- piperidinemethanols, respectively, by using electrooxidative methods in methanol. For these reactions, the yields of the corresponding cyclized compounds were significantly increased by using catalytic amounts of iodide ions. In contrast, 3-dialkylamino-1-phenylpropanols afforded the expected cyclic 6-phenyl-1,3-oxazinane derivatives using only a small excess of base. Georg Thieme Verlag Stuttgart · New York.
Synthesis of N-(dialkylaminoalkyl)alcohols by homogeneously catalyzed hydrogenolysis of cyclic N,O-acetals
Tararov, Vitali I.,Kadyrov, Renat,Riermeier, Thomas H.,B?rner, Armin
, p. 375 - 380 (2007/10/03)
The homogeneously catalyzed hydrogenation of 1,3-oxazolidines affording unsymmetrically substituted 2-N-(dialkylamino)ethanols is reported showing for the first time that Rh(I) catalysts based on chelating diphosphines can be advantageous for this reaction.
Heterogeneous rhodium-catalyzed hydrogenation conditions for the highly effective synthesis of 1,3-oxazolidines from 1,2-amino alcohols and nitriles
Letinois, Stephane,Dumur, Jean-Christophe,Henin, Francoise,Muzart, Jacques
, p. 2327 - 2330 (2007/10/03)
A procedure easily to carried out for the synthesis of 1,3-oxazolidines in high yields using 1,2-amino alcohols, nitriles, an atmospheric pressure of hydrogen and catalytic quantities of rhodium on carbon powder is presented. This reaction probably involves the semi-hydrogenation of the nitrile followed by condensation with the amine alcohol. The process may constitute the key step in a two-step sequence for reducing a nitrile into the corresponding aldehyde.
Formation of azomethine ylids by thermolysis of oxazolidines. Study of the reaction in solution and in the gaseous phase
Bureau, R.,Mortier, J.,Joucla, M.
, p. 584 - 596 (2007/10/02)
Thermolysis of oxazolidines leads to azomethine ylids via cycloreversion.In the liquid phase, these intermediates then give 1-3 dipolar cycloaddition; in the gaseous phase, they lead to aziridines.With an alkyl group in position 2, we observed also the formation of enamines.The effect of substituents on both the cycloreversion reaction and the evolution of azomethine ylids was studied.The mechanism of the process tautomerism aziridine -> azomethine ylid -> enamine is discussed.Keywords - azomethine ylids / oxazolidines / cycloreversion / aziridines / enamines / tautomerism
Reductive Cleavage of N-Substituted 2-Aryl-1,3-oxazolidines: Generation of α-Amino-Substituted Carbanions
Azzena, Ugo,Melloni, Giovanni,Nigra, Cristina
, p. 6707 - 6711 (2007/10/02)
The behavior of several N-substituted 2-aryl-1,3-oxazolidines has been investigated under conditions of electron transfer from alkali metals in aprotic solvents.The reduction led to the regioselective cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted benzylamino alcohols in good yields.Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of α-tertiary amino-substituted carbanions.
Thermal Rearrangement of some Oxazolidine N-Oxides. 2-Alkyl-6-aryl-3,4-dihydro-2H-1,5,2-dioxazines
Saba, Shahrokh,Domkowski, Patrick W.,Firooznia, Fariborz
, p. 921 - 923 (2007/10/02)
3-Alkyl-2-aryloxazolidines are oxidized with 3-chloroperoxybenzoic acid to produce the corresponding oxazolidine N-oxides.These N-oxides undergo thermal rearrangement to give 2-alkyl-6-aryl-3,4-dihydro-2H-1,5,2-dioxazines in 55-85 percent yield.
FLASH VACUUM THERMOLYSIS OF OXAZOLIDINES : A NEW WAY TO REACTIVE AZOMETHINE YLIDES. RING CLOSURE TO AZIRIDINES.
Joucla, Marc,Mortier, Jacques,Bureau, Ronan
, p. 2975 - 2976 (2007/10/02)
Flash vacuum thermolysis of oxazolidines leads to azomethine ylides which undergo ring closure to aziridines.
