scholarly journals Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

2019 ◽  
Vol 15 ◽  
pp. 1281-1288
Author(s):  
Maryna V Murlykina ◽  
Oleksandr V Kolomiets ◽  
Maryna M Kornet ◽  
Yana I Sakhno ◽  
Sergey M Desenko ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Carboxylic Acids ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Compound Library ◽  
Reaction Sequence ◽  
Scaffold Diversity ◽  
Substituted 1

Substituted 1H-pyrazolo[3,4-b]pyridine-4- and 1H-pyrazolo[3,4-b]pyridine-6-carboxamides have been synthetized through a Doebner–Ugi multicomponent reaction sequence in a convergent and versatile manner using diversity generation strategies: combination of two multicomponent reactions and conditions-based divergence strategy. The target products contain as pharmacophores pyrazolopyridine and peptidomimetic moieties with four points of diversity introduced from readily available starting materials including scaffold diversity. A small focused compound library of 23 Ugi products was created and screened for antibacterial activity.

ChemInform Abstract: Synthesis and Antibacterial Activity of New 5-Substituted 1- Cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-oxo-1,8-naphthyridine- 3-carboxylic Acids.

ChemInform ◽  
2010 ◽  
Vol 23 (50) ◽  
pp. no-no
Author(s):  
P. REMUZON ◽  
D. BOUZARD ◽  
P. DI CESARE ◽  
C. DUSSY ◽  
J.-P. JACQUET ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Carboxylic Acids ◽  
Substituted 1

scholarly journals Concise Synthesis of Macrocycles by Multicomponent Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1027-1038 ◽  
Author(s):  
Alexander Dömling ◽  
Eman Abdelraheem ◽  
Samad Khaksar
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Ring Opening ◽  
Multicomponent Reactions ◽  
Reaction Pathway ◽  
Ring Closure ◽  
Side Chains ◽  
Reaction Sequence ◽  
Cyclic Anhydride

A short reaction pathway was devised to synthesize a library of artificial 18–27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets.

Synthesis and antibacterial activity of new 5-substituted 1-cyclopropyl-6-fluoro-7-piperazinyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids

1992 ◽  
Vol 29 (4) ◽  
pp. 985-989 ◽  
Author(s):  
Philippe Remuzon ◽  
Daniel Bouzard ◽  
Pierre Di Cesare ◽  
Christian Dussy ◽  
Jean-Pierre Jacquet ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Carboxylic Acids ◽  
Substituted 1

scholarly journals A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction

2011 ◽  
Vol 7 ◽  
pp. 962-975 ◽  
Author(s):  
Christian Eidamshaus ◽  
Roopender Kumar ◽  
Mrinal K Bera ◽  
Hans-Ulrich Reissig
Keyword(s):  
Lactic Acid ◽  
Carboxylic Acids ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Practical Approach ◽  
Side Chains ◽  
Step Process ◽  
Step Procedure ◽  
Cyclocondensation Reaction

A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented.

scholarly journals An evaluation of credentials of a multicomponent reaction for the synthesis of isothioureas through the use of a holistic CHEM21 green metrics toolkit

2017 ◽  
Vol 19 (1) ◽  
pp. 249-258 ◽  
Author(s):  
S. Abou-Shehada ◽  
P. Mampuys ◽  
B. U. W. Maes ◽  
J. H. Clark ◽  
L. Summerton
Keyword(s):  
Organic Compounds ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Materials Used

Multicomponent reactions (MCRs) are considered green and material efficient methods for the synthesis of organic compounds, however very few studies have investigated the metrics of the upstream processes involved to achieve the starting materials used in these reactions.

Synthesis, Antibacterial Activity, and Toxicity of 7-(Isoindolin-5-yl)-4-oxoquinoline-3-carboxylic Acids

2011 ◽  
Vol 52 (12) ◽  
pp. 903-913 ◽  
Author(s):  
Kazuya Hayashi ◽  
Masahiro Takahata ◽  
Yasuhito Kawamura ◽  
Yozo Todo
Keyword(s):  
Antibacterial Activity ◽  
Carboxylic Acids

Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold

2016 ◽  
Vol 22 (1) ◽  
pp. 11-15 ◽  
Author(s):  
Michail N. Elinson ◽  
Fedor V. Ryzhkov ◽  
Victor A. Korolev ◽  
Mikhail P. Egorov
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Large Scale ◽  
Potassium Fluoride ◽  
Environmentally Benign ◽  
Anti Hiv

AbstractFast (3 min) pot, atom and step economics (PASE) potassium fluoride catalyzed multicomponent reaction of isatins, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one results in efficient formation of substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans in 92–96% yields. The developed ‘on-solvent’ approach to the substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans – the pharmacologically perspective substances with known antiviral, antileishmanial, anticonvulsant and anti-HIV activities – is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast and environmentally benign synthetic concept for the multicomponent reactions strategy.

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