Base catalysis of nucleophilic aromatic substitution. The reactions of primary and secondary amines with nitrophenyl phosphates

1970 ◽  
pp. 1187 ◽  
Author(s):  
A. J. Kirby ◽  
M. Younas
Keyword(s):  
Base Catalysis ◽  
Nucleophilic Aromatic Substitution ◽  
Secondary Amines ◽  
Aromatic Substitution ◽  
Primary And Secondary Amines

scholarly journals Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

2019 ◽  
Vol 15 ◽  
pp. 474-489 ◽  
Author(s):  
Andrejs Šišuļins ◽  
Jonas Bucevičius ◽  
Yu-Ting Tseng ◽  
Irina Novosjolova ◽  
Kaspars Traskovskis ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Secondary Amines ◽  
Acetonitrile Solution ◽  
Quantum Yields ◽  
Cell Labelling ◽  
Aromatic Substitution ◽  
Fluorescent Properties ◽  
Substitution Reactions ◽  
Low Cytotoxicity ◽  
Electron Donating Groups

The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future.

scholarly journals Base Catalysis and Element Effect in Nucleophilic Aromatic Substitution with p-Anisidine.

1973 ◽  
Vol 27 ◽  
pp. 191-196 ◽  
Author(s):  
Bo Lamm ◽  
Jörgen Lammert ◽  
Leif J. Sæthre ◽  
Steen Skaarup ◽  
Riitta Aaltonen ◽  
...  
Keyword(s):  
Base Catalysis ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution

Base catalysis in nucleophilic aromatic substitution

1968 ◽  
Vol 9 (45) ◽  
pp. 4699-4702 ◽  
Author(s):  
Sidney D. Ross ◽  
Raymond C. Petersen
Keyword(s):  
Base Catalysis ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution
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