Intramolecular Nucleophilic Substitution of Hydrogen in (Quinoxalinyl‐2)aminovinyl Derivatives as a New Approach to Pyrrolo‐ and Indolo[2,3‐b]quinoxalines

2004 ◽  
Vol 34 (14) ◽  
pp. 2531-2537 ◽  
Author(s):  
S. K. Kotovskaya ◽  
V. N. Charushin ◽  
N. M. Perova ◽  
M. I. Kodess ◽  
O. N. Chupakhin
Keyword(s):  
Nucleophilic Substitution ◽  
Nucleophilic Substitution Of Hydrogen ◽  
New Approach ◽  
Intramolecular Nucleophilic Substitution

scholarly journals Synthesis of Carbohydrate Based Macrolactones and Their Applications as Receptors for Ion Recognition and Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3394
Author(s):  
Surya B. Adhikari ◽  
Anji Chen ◽  
Guijun Wang
Keyword(s):  
Nucleophilic Substitution ◽  
Supramolecular Chemistry ◽  
Copper Sulfate ◽  
Substitution Reaction ◽  
Biological Properties ◽  
Anion Binding ◽  
Nucleophilic Substitution Reaction ◽  
Binding Properties ◽  
Intramolecular Nucleophilic Substitution ◽  
Leaving Groups

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Synthesis of functionalised bipyridines by sequential nucleophilic substitution of hydrogen and cycloaddition in 1,2,4-triazine rings

2002 ◽  
Vol 12 (1) ◽  
pp. 30-31 ◽  
Author(s):  
Dmitry N. Kozhevnikov ◽  
Valery N. Kozhevnikov ◽  
Tatiana V. Nikitina ◽  
Vladimir L. Rusinov ◽  
Oleg N. Chupakhin ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nucleophilic Substitution Of Hydrogen
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