Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole

2008 ◽  
Vol 86 (7) ◽  
pp. 682-685 ◽  
Author(s):  
Barbara Szpakiewicz ◽  
Maria Grzegożek
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Para Position ◽  
Basic Medium ◽  
Ortho Position ◽  
Vicarious Nucleophilic Substitution

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 175-181
Author(s):  
Mieczysław Mąkosza ◽  
Małgorzata Bechcicka ◽  
Krzysztof Wojciechowski
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Nitro Compounds ◽  
Simple Synthesis ◽  
Para Position ◽  
Crucial Step ◽  
Vicarious Nucleophilic Substitution ◽  
Aromatic Nitro Compounds ◽  
Leaving Group ◽  
Aromatic Nitro

Acetals of dimethyl phenyl- and heteroaryl-α-hydroxymethanephosphonates were deprotonated to generate carbanions, which enter the vicarious nucleophilic substitution (VNS) of hydrogen in aromatic nitro compounds to form 4-nitrobenzhydrylphosphonates and α-heteroaryl-4-nitrobenzylphosphonates. Similarly acetals of cyano­hydrins of heteroaromatic aldehydes (furfural and 2-formylthiophene) react to form heteroaryl 4-nitroarylacetonitriles. The anion of the hemiacetal of acetaldehyde is an efficient leaving group in the base-induced β-elimination step – the crucial step in the VNS reaction. The reaction selectively occurred at the para-position to the nitro group.

scholarly journals Design, synthesis, characterization and in vivo studies of some hydroxylated chalcone derivatives as hypoglycemic agents

2020 ◽  
Vol 1 (1) ◽  
pp. 10-14
Author(s):  
Animeshchandra G. M. Haldar ◽  
Santosh Subhash Chhajed ◽  
Akanksha Ravindra Ugale ◽  
Sanjay J. Kshirsagar ◽  
Kanhaiya Murlidhar Dadure ◽  
...  
Keyword(s):  
Blood Glucose ◽  
Blood Glucose Level ◽  
Glucose Level ◽  
Para Position ◽  
In Vivo Studies ◽  
Hypoglycemic Agents ◽  
Basic Medium ◽  
Diabetic Rat ◽  
Ortho Position ◽  
Chalcone Derivatives

Introduction: Low molecular weight ligands (LMWL) have a citadel reputation in the modulation of numerous therapeutic targets as a result of their smart uniqueness. The hydroxylated chalcone derivatives have been reported to be therapeutic agents owing to their capability to demonstrate multifarious pharmacological activities, however, their potential in lowering blood glucose levels is not yet explored fully. Methods: Corresponding aldehydes and acetophenones were made to react in an alcoholic basic medium to produce the desired chalcone scaffolds. The anti-hyperglycemic potentials of the derivatives were studied using the streptozotocin-induced diabetic rat model. Compounds 3d, 3f, 3g, 3h, and 3j demonstrated excellent anti-hyperglycemic activity. Results: Chalcone 3d, having an ortho-methoxy substituent in B-ring, displayed the highest hypoglycemic potential with a 26.9% lowering of blood glucose level compared to standard acarbose which exhibited a 34.7% reduction. Compounds 3a, 3c, and 3e showed the lowest activity. Discussion: The study revealed the potential of chalcone scaffolds in lessening the blood glucose level by 7.1% to 26.9%. The ortho-position was observed to be high opportunistic for inducing the hypoglycemia activity as compared to para-position and para-position is, in turn, advantageous to the meta-position. Conclusions: The role of various substituents in modulating this enzyme function was studied. The electron-donating groups were found to be effectual for modulation of the anti-diabetic target compared to electron-withdrawing groups.

ChemInform Abstract: Asymmetric Aromatic Vicarious Nucleophilic Substitution of Hydrogen.

ChemInform ◽  
2010 ◽  
Vol 28 (23) ◽  
pp. no-no
Author(s):  
M. D. DREW ◽  
D. A. JACKSON ◽  
N. J. LAWRENCE ◽  
J. LIDDLE ◽  
R. G. PRITCHARD
Keyword(s):  
Nucleophilic Substitution ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Vicarious Nucleophilic Substitution
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