1345015-07-7Relevant 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.
, p. 6663 - 6667 (2018)
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.
Nickel-catalyzed dehydrogenative [4 + 2] cycloaddition of 1,3-dienes with nitriles
Ohashi, Masato,Takeda, Ippei,Ikawa, Masashi,Ogoshi, Sensuke
, p. 18018 - 18021 (2011/12/13)
Pyridines, which comprise one of the most important classes of the six-membered heterocyclic compounds, are widely distributed in nature, and the transition-metal-catalyzed [2 + 2 + 2] cycloaddition reaction of two alkynes and a nitrile is one of the most powerful methods for preparing versatile, highly substituted pyridine derivatives. However, the lack of chemo- and regioselectivity is still a crucial issue associated with fully intermolecular [2 + 2 + 2] cycloaddition. The present study developed the Ni(0)-catalyzed intermolecular dehydrogenative [4 + 2] cycloaddition reaction of 1,3-butadienes with nitriles to give a variety of pyridines regioselectively.
