5866-28-4Relevant academic research and scientific papers
Toluene and its Derivatives as Atom-Efficient Benzylating Agents for Secondary Amines
Sch?nbauer, David,Lukas, Florian,Schnürch, Michael
, p. 94 - 98 (2019/01/04)
Toluene as a replacement for common N -benzylating agents, such as benzyl bromide, can be an atom-efficient alternative reagent. Under nickel catalysis and mildly oxidative conditions, it is possible to activate toluene efficiently and use it directly for the benzylation of different 2-aminopyridines. The transformation is not restricted to simple toluene, but also substituted derivatives give the desired product in good yields. Effective cleavage of the pyridine moiety is presented.
Copper-catalyzed intramolecular dehydrogenative aminooxygenation: Direct access to formyl-substituted aromatic N-heterocycles
Wang, Honggen,Wang, Yong,Liang, Dongdong,Liu, Lanying,Zhang, Jiancun,Zhu, Qiang
supporting information; experimental part, p. 5678 - 5681 (2011/08/02)
A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper-mediated oxygen activation process via a peroxy-copper(III) intermediate. Copyright
General and mild preparation of 2-aminopyridines
Londregan, Allyn T.,Jennings, Sandra,Wei, Liuqing
supporting information; experimental part, p. 5254 - 5257 (2011/02/24)
A general and facile one-pot amination procedure for the synthesis of 2-aminopyridines from the corresponding pyridine-N-oxides is presented as a mild alternative to SNAr chemistry. A variety of amines and heterocyclic-N-oxides participate effectively in this transformation which uses the phosphonium salt, PyBroP, as a means of substrate activation.
Preparation of the maleic anhydride nucleus from dichloro γ-lactams: Focus on the role of the N-substituent in the functional rearrangement and in the hydrolytic steps
Ghelfi, Franco,Pattarozzi, Mariella,Roncaglia, Fabrizio,Parsons, Andrew F.,Felluga, Fulvia,Pagnoni, Ugo M.,Valentin, Ennio,Mucci, Adele,Bellesia, Franco
experimental part, p. 3131 - 3141 (2009/04/06)
The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro γ-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide. Georg Thieme Verlag Stuttgart.
A mild, catalyst-free synthesis of 2-aminopyridines
Poola, Bhaskar,Choung, Wonken,Nantz, Michael H.
, p. 10798 - 10801 (2008/12/23)
Alkylation of 2-mercaptopyridine with 1,2-dibromoethane affords a cyclic dihydrothiazolopyridinium salt that can serve as a precursor of 2-aminopyridines. Its reaction with primary or secondary amines, either neat or in DMSO, under mild conditions gives the title compounds.
New efficient RCM-mediated synthesis of pyrrolidine derivatives
Majumdar, Krishna C.,Chakravorty, Santanu,Taher, Abu
, p. 3159 - 3169 (2008/12/22)
Fast and effective ring-closing olefin metathesis (RCM) of diallyamine derivatives of coumarin, quinolone, pyridine, and substituted benzene, using first-generation RCM ruthenium-based catalyst, leads to corresponding pyrrolidine derivatives in 70-95% yie
Synthesis of a β-strand mimetic based on a pyridine scaffold
Blomberg, David,Brickmann, Kay,Kihlberg, Jan
, p. 10937 - 10944 (2007/10/03)
A synthetic route to a 2,4-disubstituted pyridine as a potential β-strand mimetic has been developed and applied in the synthesis of a tripeptidomimetic of Leu-Gly-Gly. The pyridine scaffold replaces the central glycine, and is substituted with analogues
Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines
Jaime-Figueroa, Saul,Liu, Yanzhou,Muchowski, Joseph M.,Putman, David G.
, p. 1313 - 1316 (2007/10/03)
A series of anilines and heteroarylamines were synthesized in moderate to excellent yields by palladium catalyzed cross coupling reaction of aryl or heteroaryl halides with allyl- or N,N-diallylamine followed by deallylation.
