Synthesis of ferrocenyl quinolines…

In summary, we have developed a highly versatile, high yielding and easy to perform one-pot synthesis of highly substituted 2-aminoquinolines and heterocyclic derivatives. Key features include broadly available stating materials, convenient product separation and purification by precipitation and diverse product structures. Our procedure will be of general use due to the privileged structure character of the 2-aminoquinoline.

InCl3-Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope ..

Polysubstituted quinolines are synthesized through an unprecedented cascade annulation of ω-azido-1-alkynes with diaryliodonium salts, which serve as C2-building blocks. The reaction proceeds smoothly and is catalyzed by Cu(I) catalysts to give various quinolines in good isolated yields with simple operation under mild conditions.


Quinoline - Infogalactic: the planetary knowledge core

Quinolines are often synthesized from simple anilines using a number of named reactions

The intramolecular hydrogen bridge in 2-aminoquinoline-3-carboxamides is an important observation as it can reduce the hydrophilic character of the compounds in a biological setting and can potentially facilitate transmembrane transport. Adjacent hydrogen bond donor and acceptor moieties in a molecule can lead to the temporary formation of ring systems and open conformations with differential exposure of the polar groups to the solvent. The formation of an intramolecular hydrogen bond mediated ring should effectively remove one donor and one acceptor function from the surface of a molecule and thus result in increased lipophilicity leading to an increase of membrane permeability and a reduction of aqueous solubility. In fact multiple measurements of the passive permeability, the octanol/water partition coefficient and kinetic solubility in related systems support this hypothesis. Recently we observed similar intramolecular hydrogen bridges during our synthesis of 2-aminothiophene-3-carboxamides.,


Niementowski quinazoline synthesis; Niementowski quinoline synthesis;

Quinoline was first extracted from in 1834 by . Coaltar remains the principal source of commercial quinoline. It can besynthesized using various methods:

Chapter 7 Quinolines and Isoquinolines

The direct condensation of 2-aminobenzaldehyde (4) with cyanoacetamide (11) is rarely reported and the scope and limitations are not described. Based on the recently described facile and convenient access to multiple cyanoacetamides as starting materials for an interesting group of multicomponent and other reactions we herein would like to report a more convenient method to prepare 2-aminoquinoline-3-carboxamides (8) from aminobenzaldehydes and cyanoacetamides.-

Niementowski quinoline synthesis ..

Quinoline is mainly used as a building block to other specialtychemicals. Approximately 4 are produced annually according to areport published in 2005. Its principal use is as a precursor to , which is a versatilechelating agent and precursor to pesticides. Its and derivatives areprecursors to . Oxidation of quinolineaffords (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide soldunder the name "Assert".

quinolines ( 4 ) via a Schiff base ..

All compounds precipitated while the reaction cooled down. As a result, the purification was as easy as simply collecting the solid after filtration. All products indicate excellent purity by NMR and LC-MS (). We were able to grow several single crystals suitable for X-ray structure determination. shows the identity and orientation of 8{7,24} and 19a in the crystalline state. It is noteworthy that the 2- aminoquinoline substructure makes extensive hydrogen bonding contacts via the amidine substructure. The phenyl substructure of the 2-aminoquinoline on the other hand makes multiple intra and intermolecular hydrophobic contacts (). The carbonyl oxygen of the 3-carboxamide forms a 6-membered ring involving an intramolecular hydrogen bridge in both structures.