15082-42-5Relevant articles and documents
Developing Lithium Chemistry of 1,2-Dihydropyridines: From Kinetic Intermediates to Isolable Characterized Compounds
Armstrong, David R.,Harris, Catriona M. M.,Kennedy, Alan R.,Liggat, John J.,McLellan, Ross,Mulvey, Robert E.,Urquhart, Matthew D. T.,Robertson, Stuart D.
, p. 14410 - 14420 (2015)
Generally considered kinetic intermediates in addition reactions of alkyllithiums to pyridine1-lithio-2-alkyl-1,2-dihydropyridines have been rarely isolated or characterized. This study develops their "isolated" chemistry. By a unique stoichiometric (that is1:1alkyllithium/pyridine ratios) synthetic approach using tridentate donors we show it is possible to stabilize and hence crystallize monomeric complexes where alkyl is tert-butyl. Theoretical calculations probing the donor-free parent tert-butyl species reveal 12 energetically similar stereoisomers in two distinct cyclotrimeric (LiN)3 conformations. NMR spectroscopy studies (including DOSY spectra) and thermal volatility analysis compare new sec-butyl and iso-butyl isomers showing the former is a hexane soluble efficient hydrolithiation agent converting benzophenone to lithium diphenylmethoxide. Emphasizing the criticalness of stoichiometryreaction of nBuLi/Me6TREN with two equivalents of pyridine results in non-alkylated 1-lithio-1,4-dihydropyridine·Me6TREN and 2-n-butylpyridineimplying mechanistically the kinetic 1,2-n-butyl intermediate hydrolithiates the second pyridine.
Experimental and computational studies of borohydride catalyzed hydrosilylation of a variety of C=O and C=N functionalities including esters, amides and heteroarenes
Manas, Michael G.,Sharninghausen, Liam S.,Balcells, David,Crabtree, Robert H.
supporting information, p. 1694 - 1700 (2014/05/06)
Sodium borohydride and a series of related borohydrides catalyze a transition metal-free hydrosilylation of a variety of C=O and C=N functionalities under mild conditions. Importantly, many of these reactions are possible using the cheap and environmentally benign hydrosilane polymethylhydrosiloxane. A mechanism is proposed based on experimental and computational results.
NAPHTHYRIDINES WHICH AFFECT IL-4 AND G-CSF
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Page 32, (2010/02/07)
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