Journal ArticleDOI
Syntheses, with the aid of (4-pyridyl)-magnesium chloride, of 4-lithiopyridine and of 3-lithioquinoline
J. P. Wibaut,L. G. Heeringa +1 more
TLDR
In this paper, 4-Chloropyridine can be converted for about 70% into a complex magnesium compound, which reacts in the manner of a Grignard compound with aldehydes or ketones, forming (4-pyridyl)-carbinols.Abstract:
4-Chloropyridine can be converted for about 70% into a complex magnesium compound, which reacts in the manner of a Grignard compound with aldehydes or ketones, forming (4-pyridyl)-carbinols; with orthoformic ester, (4-pyridyl)-methanal-acetal is formed.
The reaction of 4-lithiopyridine with benzophenone and with ethyl benzoate respectively leads to the formation of (4-pyridyl)-diphenyl-carbinol and to bis-(4-pyridyl)-phenyl-carbinol respectively. With aromatic nitriles, (4-pyridyl)-aryl ketones are formed.
The reactions of 4-lithiopyridine with cyanopyridines or with pyridine-carboxylic esters lead to the formation of bis-pyridyl ketones, e.g., bis-(4-pyridyl) ketone.
Quinolyl ketones are obtained by starting from 3-lithioquinoline.read more
Citations
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Journal ArticleDOI
Nucleophilic dearomatizing (DNAr) reactions of aromatic C,H-systems. A mature paradigm in organic synthesis.
Fernando López Ortiz,María José Iglesias,Ignacio Fernández,Carmen M. Andujar Sanchez,Gloria Ruiz Gomez +4 more
Journal ArticleDOI
Pyridine elaboration through organometallic intermediates: regiochemical control and completeness
TL;DR: This approach relies on organometallic methods, which are both efficacious and extremely flexible as far as the substitution site and the product structure are concerned (86 references).
Journal ArticleDOI
Using long bis(4-pyridyl) ligands designed for the self-assembly of coordination frameworks and architectures
TL;DR: In this article, five long bis(4-pyridyl) ligands with different tether groups were synthesized and employed for the self-assembly of coordination polymers and architectures, with the aim of obtaining structural motifs characterized by long metal-metal separations.
Journal ArticleDOI
Flow microreactor synthesis of disubstituted pyridines from dibromopyridinesviaBr/Li exchange without using cryogenic conditions
Aiichiro Nagaki,Shigeyuki Yamada,Masatomo Doi,Yutaka Tomida,Naofumi Takabayashi,Jun-ichi Yoshida +5 more
TL;DR: A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed, and the cryogenic conditions required for conventional batch macro processes can be avoided.
Book ChapterDOI
Generation and Reactions of sp2-Carbanionic Centers in the Vicinity of Heterocyclic Nitrogen Atoms
TL;DR: In this paper, the authors discuss that the generation of a carbanionic center adjacent to a neutral heteroatom such as nitrogen is often a difficult proposition and this is a consequence of several factors, of which charge repulsion by the heteroatomic lone pair, low acidity of the hydrogen to be abstracted, and undesired reaction at other reactive sites in the molecule are all major deterents.
References
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Histamine antagonists; basically substituted pyridine derivatives.
Journal ArticleDOI
A Study of the Preparation of Alpha-Pyridyl Halides from Alpha-Aminopyridine by the Diazo Reaction
Journal ArticleDOI
Organometallic Derivatives of Carbazole and Quinoline. Amides of 3-Quinoline-carboxylic Acid
Henry Gilman,Sydney M. Spatz +1 more