vicarious nucleophilic substitution
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Synlett ◽  
2021 ◽  
Author(s):  
RuShuang Zhou ◽  
Chun Cai

This manuscript describes the C-H amination of a variety of nitro aza-heterocyclic compounds by Vicarious Nucleophilic Substitution (VNS) methodology with 4-amino-1,2,4-triazole (ATA). The aminated products were characterized by NMR, MS and single-crystal X-ray diffraction. Among the substrates examined, moderate to excellent yield (30-88%) and good regioselectivity (ortho/para position of the nitro) are exhibited. This protocol offers the advantages of mild conditions, short reaction time (only 2-4 h) with inexpensive, commercially available and less toxic amination reagent, no additional catalysts or reagents needed. Possible reaction mechanism was also discussed.


Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 1857
Author(s):  
Jakub Wantulok ◽  
Daniel Swoboda ◽  
Jacek E. Nycz ◽  
Maria Książek ◽  
Joachim Kusz ◽  
...  

The vicarious nucleophilic substitution of hydrogen (VNS) reaction in electron-deficient nitroquinolines was studied. Properties of all new products have been characterized by several techniques: MS, HRMS, FTIR, GC-MS, electronic absorption spectroscopy, and multinuclear NMR. The structures of 4-chloro-8-nitroquinoline, 8-(tert-butyl)-2-methyl-5-nitroquinoline, 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one were determined by single-crystal X-ray diffraction measurements. The 9-(8-nitroquinolin-7-yl)-9H-carbazole and (Z)-7-(9H-carbazol-9-yl)-8-(hydroxyimino)quinolin-5(8H)-one illustrate the nitro/nitroso conversion within VNS reaction. Additionally, 9-(8-isopropyl-2-((8-isopropyl-2-methyl-5-nitroquinolin-6-yl)methyl)-5-nitrosoquinolin-6-yl)-9H-carbazole is presented as a double VNS product. It is postulated that the potassium counterion interacts with the oxygen on the nitro group, which could influence nucleophile attack in that way.


Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 175-181
Author(s):  
Mieczysław Mąkosza ◽  
Małgorzata Bechcicka ◽  
Krzysztof Wojciechowski

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.


Synlett ◽  
2020 ◽  
Vol 31 (11) ◽  
pp. 1094-1096
Author(s):  
Michael F. Greaney ◽  
Fayez Y. Al-Mkhaizim

A highly selective C–H functionalization of nitrobenzenes and nitropyridines is reported using tandem vicarious nucleophilic substitution (VNS) chemistry with electrophilic fluorination using Selectfluor®. The process generates tertiary benzylic fluorides in good yield under simple, mild conditions and short reaction times.


2019 ◽  
Vol 38 (10) ◽  
pp. 2278-2279 ◽  
Author(s):  
Markus Jochriem ◽  
Dominik Bosch ◽  
Holger Kopacka ◽  
Benno Bildstein

2019 ◽  
Vol 43 (36) ◽  
pp. 14355-14367 ◽  
Author(s):  
Mohammed Eddahmi ◽  
Nuno M. M. Moura ◽  
Latifa Bouissane ◽  
Ahmed Gamouh ◽  
Maria A. F. Faustino ◽  
...  

Efficient synthesis of new N-methylnitroindazolylacetonitriles and their ability to switch between tautomeric forms in the presence of anionic species.


Synlett ◽  
2018 ◽  
Vol 29 (14) ◽  
pp. 1842-1846 ◽  
Author(s):  
Lamouri Hammal ◽  
Laurent El Kaïm ◽  
Samira Baaziz ◽  
Mansour Kerim ◽  
Marie Cordier

A two-step isoindolone synthesis has been achieved by using an Ugi/oxidative vicarious nucleophilic substitution sequence starting from 3-nitrobenzoic acid and aromatic aldehydes. Loss of the amido group was observed as well as a further oxidative process towards hydroxyisoindolone derivatives after prolonged stirring open to the atmosphere.


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