- Design and synthesis of some novel 7-substituted thiosemicarbazinyl-quinolines via Ullmann coupling reaction and examination of their antimicrobial activities
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Abstract: The present work demonstrates functionalization of 4,7-dichloro quinoline via a modified Ullmann coupling reaction concept of varying oxidation state and reaction conditions. Based on these conditions, novel 2-(4-morpholino quinolin-7-yl)-N-substituted phenyl hydrazinyl carbothioamide derivatives have been synthesized. Structures of the final synthesized compounds including intermediates were confirmed by IR, 1H NMR and 13C NMR spectral studies. Examination of biological profiles was carried out against various strains of micro-organisms. SAR and HOMO–LUMO calculations were carried out for judicious design. Graphical Abstract: [Figure not available: see fulltext.].
- Patel, Jankiben J.,Patel, Anuj P.,Chikhalia, Kishor H.
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- Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates
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Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.
- Staderini, Matteo,Bolognesi, Maria Laura,Menndez, J. Carlos
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supporting information
p. 185 - 195
(2015/01/30)
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- Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
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Focused microwave irradiation of equimolecular mixtures of 9-chloroacridines, 4-chloroquinolines and 4-chloroquinazolines with amines in the presence of 2 equiv of phenol allows the general, fast and high-yielding synthesis of aminated heterocycles, with a very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic problem of achieving a practical and efficient method for the amination of π-deficient nitrogen heterocycles for medicinal chemistry applications.
- Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menéndez, J. Carlos
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p. 1024 - 1030
(2013/02/23)
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- Microwave-accelerated solvent- and catalyst-free synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles
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An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equiv.) was separately treated with 2-aminophenol (2 equiv.) and 4-aminophenol (2 equiv.), 4-(2'-hydroxyphenyl)-7-chloroquinoline and 4-(4'-hydroxyphenyl)-7-chloroquinoline, respectively, were formed. CSIRO 2007.
- Motiwala, Hashim F.,Kumar, Raj,Chakraborti, Asit K.
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p. 369 - 374
(2008/02/11)
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- A convenient synthesis of nitrogen-containing heterocycles bearing amino substituents from heteroaryl triflates
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Nitrogen-containing heterocycles bearing amino substituents were prepared by the reaction of the corresponding nitrogen-containing heteroaryl triflates with amines. The reaction affords good results with primary and secondary amines, and with aliphatic and aromatic amines. The whole triflation/amination process can also be conducted as a one-pot operation.
- Cacchi, Sandro,Carangio, Antonella,Fabrizi, Giancarlo,Moro, Leonardo,Pace, Paola
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p. 1400 - 1402
(2007/10/03)
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- Antimalarial 6-aminoquinolines. XV. 6- and 4-Aminoquinolines with tertiary basic alkylated amino-group
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Antimalarial 6-aminoquinolines were acylated and alkylated at the secondary aromatic 6-amino group with the aim of studying the influence of a tertiary aromatic 6-amino group on antimalarial activity and toxicity. Four derivatives of 4-amino-7-chloroquinoline with a tertiary aromatic 4-amino group were synthesized to study the influence of such a variation on the biological activity of the 4-aminoquinolines. The N-alkylated derivatives were active against malaria (P. vinckei/mice).
- Dann,Steuding,Lisson,Seidel,Fink,Nickel
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p. 1219 - 1223
(2007/10/02)
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