19490-93-8Relevant academic research and scientific papers
Synthesis of Polyfunctionalized Triaryllanthanum Reagents by Using Ph3La and Related Species as Exchange Reagents
Benischke, Andreas D.,Anthore-Dalion, Lucile,Kohl, Fabien,Knochel, Paul
supporting information, p. 11103 - 11109 (2018/08/09)
Ph3La?5 LiCl and the related (m-xylyl)3La?5 LiCl were used as Hal/La exchange reagents (Hal=Br, I) for the preparation of various triaryl- and triheteroaryl-lanthanum derivatives. These new exchange reagents are compatible with isoquinolines and some functional groups such as a nitrile or an ester. The reactivity of the resulting lanthanum compounds towards electrophiles, such as ketones, aldehydes, N,N-dimethylamides, and primary alkyl halides was investigated. Additionally, a Pd-catalyzed cross-coupling procedure with aryl bromides was developed.
Naphthalene-catalysed lithiation of chlorinated nitrogenated aromatic heterocycles and reaction with electrophiles
Gómez, Inmaculada,Alonso, Emma,Ramón, Diego J.,Yus, Miguel
, p. 4043 - 4052 (2007/10/03)
Naphthalene catalysed reductive lithiation of various chloroazines (1, 7, 10, 13) in the presence of different electrophiles yields, after hydrolysis, the expected functionalised heterocycles with one (2, 8), two (11, 14a-d) and three nitrogen atoms in the ring (14e,f). This methodology allowed us to trap in situ the lithium imine derived from the reaction of 2- pyridyllithium with benzonitrile, by reaction with a Grignard reagent in the presence of titanium alkoxides. 2,4-Dimethoxypyrimidines (14a,c,d) are demethylated under acidic conditions to give the corresponding uracil derivatives 16. (C) 2000 Elsevier Science Ltd.
REACTIONS OF PYRIDYL AND QUINOLYL SULFOXIDES WITH GRIGNARD REAGENT : A CONVENIENT PREPARATION OF PYRIDYL AND QUINOLYL GRIGNARD REAGENTS
Furukawa, Naomichi,Shibutani, Tadao,Matsumura, Kazunori,Fujihara, Hisashi,Oae, Shigeru
, p. 3899 - 3902 (2007/10/02)
3-,4-Pyridyl and 4-quinolyl Grignard reagents were generated by the reaction of the corresponding phenyl sulfoxides with PhMgBr and give the adducts upon treatment with various aldehydes and ketones.The stereochemistry for the reaction was investigated.
Applications of Organolithium and Related Reagents in Synthesis. Part 3. A General Study of the Reaction of Lithium Alkyls with Pyridine Ketones
Epsztajn, Jan,Bieniek, Adam
, p. 213 - 220 (2007/10/02)
The reaction of MeLi and PhLi with acetylpyridines (1a-c) and their annelated derivatives (2a), (2b), (3), and (4) has been examined.The 3- and 4-pyridyl ketones (1b), (1c), (3), and (4) gave similar results to acetophenone and 3,4-dihydronaphthalen-1(2H)-one.In the case of the 2-pyridyl ketones (1a), (2a), and (2b) unexpectedly low yields of products resulted from the addition of RLi to the carbonyl group; the reaction was efficiently enhanced by initially adding an additional amount of LiBr.These results were accounted for by the chelation of RLi or LiBr by the 2-pyridyl ketones.
