90554-53-3Relevant academic research and scientific papers
N-Silylenamines as Reactive Intermediates: Hydroamination for the Modular Synthesis of Selectively Substituted Pyridines
Lui, Erica K. J.,Hergesell, Daniel,Schafer, Laurel L.
supporting information, p. 6663 - 6667 (2018/11/21)
A modular and selective synthesis of mono-, di-, tri-, tetra-, and pentasubstituted pyridines is reported. Hydroamination of alkynes with N-silylamine using a bis(amidate)bis(amido)titanium(IV) precatalyst furnishes the regioselective formation of N-silylenamines. Addition of α,β-unsaturated carbonyls to the crude mixtures followed by oxidation affords 47 examples of pyridines in yields of up to 96%. This synthetic route allows for the synthesis of diverse pyridines containing variable substitution patterns, including pharmaceutically relevant 2,4,5-trisubstituted pyridines, using this one-pot protocol.
Ruthenium-catalyzed decarboxylative and dehydrogenative formation of highly substituted pyridines from alkene-tethered isoxazol-5(4H)-ones
Okamoto, Kazuhiro,Sasakura, Kohei,Shimbayashi, Takuya,Ohe, Kouichi
supporting information, p. 988 - 990 (2016/08/13)
A ruthenium-catalyzed reaction of alkene-tethered isoxazol-5(4H)-ones affording pyridines has been developed. Di-, tri-, and tetrasubstituted pyridines were obtained from various isoxazolones in good yields.
Cross Mannich Reaction of Aldehydes; Efficient Synthesis of Substituted Pyridines
Winter, Andreas,Risch, Nikolaus
, p. 2667 - 2670 (2007/10/03)
Symmetrically and unsymmetrically substituted pyridines were obtained in highly efficient one-pot procedures starting from α-unbranched aldehydes and iminium salts.
Novel Synthesis of 3,5-Disubstituted Pyridines by 1,4-Cycloaddition of 1-Aza-1,3-butadienes with Enamines
Komatsu, Mitsuo,Takamatsu, Shigeki,Uesaka, Masatoshi,Yamamoto, Shinji,Ohshiro, Yoshiki,Agawa, Toshio
, p. 2691 - 2699 (2007/10/02)
A new method for the synthesis of 3,5-disubstituted pyridines is described.Reactions of the N-substituted methanimines 1 with the β-substituted enamines 2 give 1-aza-1,3-butadienes 3a-3i and/or symmetrically 3,5-disubstituted pyridines 4a-c,e-h in moderate to good yields.At reaction temperatures of 150 deg C the azadienes 3 are the predominant products, and the reaction provides a good route to 1-azadienes with no substituent at the 4-position.At reaction temperatures of 200 deg C, and particularly using N-tert-butylmethanimine 1a and p-toluenesulfonic acid catalyst, the principal products are symmetrically 3,5-disubstituted pyridines.The cycloaddition was shown to proceed via the azabutadiene intermediate 3.Reactions of 3 with the enamines 2 lead to unsymmetrically 3,5-disubstituted pyridines.The mechanisms of these cycloadditions are discussed.
