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Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules.

ABSTRACT: A number of new 2-methyl- and 2-arylvinyl-3-nitropyridines were synthesized and their reactions with thiols were studied. It was found that 3-NO₂ tends to be selectively substituted under the action of sulfur nucleophiles in the presence of another nucleofuge in position 5. Correlations between the substitution pattern and regioselectivity as well as photophysical properties were established. Some synthesized compounds possessed a large Stokes shift.

SUBMITTER: Nikol'skiy VV

PROVIDER: S-EPMC9457606 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

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Nucleophilic Functionalization of 2-R-3-Nitropyridines as a Versatile Approach to Novel Fluorescent Molecules.

Nikol'skiy Vladislav V VV Minyaev Mikhail E ME Bastrakov Maxim A MA Starosotnikov Alexey M AM

Molecules (Basel, Switzerland) 20220903 17

A number of new 2-methyl- and 2-arylvinyl-3-nitropyridines were synthesized and their reactions with thiols were studied. It was found that 3-NO<sub>2</sub> tends to be selectively substituted under the action of sulfur nucleophiles in the presence of another nucleofuge in position 5. Correlations between the substitution pattern and regioselectivity as well as photophysical properties were established. Some synthesized compounds possessed a large Stokes shift. ...[more]

PMID: 36080461

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