17408-47-8Relevant academic research and scientific papers
Benzoyl peroxide promoted radical ortho-alkylation of nitrogen heteroaromatics with simple alkanes and alcohols
Fang, Lei,Chen, Liangshun,Yu, Jianjun,Wang, Limin
supporting information, p. 1910 - 1914 (2015/03/18)
A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols leads to the corresponding 2-alkylpyridines with high regioselectivity in moderate to good yields without an additional reduction step to remove the activated group. A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols has been developed. The strategy allowed convenient access to various 2-alkylpyridines in moderate to good yields without an additional reduction step to remove the activated group.
Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes
Mousseau, James J.,Bull, James A.,Ladd, Carolyn L.,Fortier, Angelique,Sustac Roman, Daniela,Charette, Andre B.
, p. 8243 - 8261 (2012/01/03)
Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.
Catalytic asymmetric hydrogenation of N-iminopyridinium ylides: Expedient approach to enantioenriched substituted piperidine derivatives
Legault, Claude Y.,Charette, Andre B.
, p. 8966 - 8967 (2007/10/03)
We have developed an efficient catalytic enantioselective hydrogenation of pyridine derivatives. Enhanced reactivity was possible by an optimization of the electronic properties of the catalyst through ligand modification. This methodology shows the parti
Highly efficient synthesis of o-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides
Legault, Claude,Charette, Andre B.
, p. 7119 - 7122 (2007/10/03)
An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.
Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines
Legault, Claude,Charette, Andre B.
, p. 6360 - 6361 (2007/10/03)
Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, sho
Chemospecificity and Regioselectivity during Cycloaddition Reactions of Diazoalkanes with 1H-1,2-Diazepines
Gesche, Paul,Klinger, Francois,Mueller, Wolfgang,Streith, Jacques,Strub, Henri,Sustmann, Reiner
, p. 4682 - 4706 (2007/10/02)
1H-1,2-Diazepines 1 react in a chemospecific way, but only regioselectively, at the 4-double bond with diazoalkanes to form "direct" and "inverse" pyrazolinodiazepines (3, 4, 6-21).A dramatic rate increase is observed when going from diazomethane to diazo
