Synthesis of 2-Methyl-3-nitropyridines, 2-Styryl-3-nitropyridines and Their Reactions with S-Nucleophiles

Synthesis of 2-Methyl-3-nitropyridines, 2-Styryl-3-nitropyridines and Their Reactions with S-Nucleophiles Full article

Journal

Chemistry proceedings
ISSN: 2673-4583

Output data

Year: 2021, Volume: 3, Number: 1, Article number : 144, Pages count : DOI: 10.3390/ecsoc-24-08324

Authors

Nikol’skiy Vladislav ^1,2 , Starosotnikov Alexey ² , Bastrakov Maxim ²

Affiliations

1	Chemistry Department, Lomonosov Moscow State University, Leninskie Gory, 1/3, 119991 Moscow, Russia
2	N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia

One of the most important and flexible tools for nitroarenes functionalization is nucleophilic aromatic substitution (SNAr). This reaction generally requires a number of conjugated electron-withdrawing groups and SNAr of non-activated nitro groups is rather uncommon. Most of these examples were obtained on polynitrobenzenes, but little is known about reactions of non-activated 3-nitropyridines. Here we report the synthesis of several 2-methyl-3-nitropyridines and their reactions with various aromatic aldehydes, leading to corresponding 2-styrylpyridines under mild conditions. Both 2-methyl- and 2-styryl-3-nitropyridines readily react with thiolate-anions and give substitution products in good yields. Chemoselectivity and regioselectivity is discussed, while some 2-styrylpyridines also showed remarkable fluorescent properties.

Nikol’skiy V. , Starosotnikov A. , Bastrakov M.
Synthesis of 2-Methyl-3-nitropyridines, 2-Styryl-3-nitropyridines and Their Reactions with S-Nucleophiles
Chemistry proceedings. 2021. V.3. N1. 144 . DOI: 10.3390/ecsoc-24-08324 OpenAlex

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