The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

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Intramolecular Aromatic Nucleophilic Substitution of the Benzimidazole-Activated Nitro Group.

ChemInform ◽

10.1002/chin.200416149 ◽

2004 ◽

Vol 35 (16) ◽

Author(s):

Tomasz Fekner ◽

Judith Gallucci ◽

Michael K. Chan

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group ◽

Aromatic Nucleophilic Substitution

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Nucleophilic substitution of the nitro group in 1-substituted 3-nitro-1H-1,2,4-triazoles in ethanolic potassium hydroxide

Chemistry of Heterocyclic Compounds ◽

10.1007/s10593-020-02780-8 ◽

2020 ◽

Vol 56 (8) ◽

pp. 1100-1102

Author(s):

Ani H. Hasratyan ◽

Astkhik А. Sukoyan ◽

Aleksan G. Shakhatuni ◽

Gevorg G. Danagulyan ◽

Hovhannes S. Attaryan

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group ◽

Potassium Hydroxide

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Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction

Synthesis ◽

10.1055/s-0040-1707230 ◽

2020 ◽

Vol 53 (01) ◽

pp. 175-181

Author(s):

Mieczysław Mąkosza ◽

Małgorzata Bechcicka ◽

Krzysztof Wojciechowski

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group ◽

Nitro Compounds ◽

Simple Synthesis ◽

Para Position ◽

Crucial Step ◽

Vicarious Nucleophilic Substitution ◽

Aromatic Nitro Compounds ◽

Leaving Group ◽

Aromatic Nitro

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.

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Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes

Synlett ◽

10.1055/s-0040-1705960 ◽

2020 ◽

Author(s):

Alexey M. Starosotnikov ◽

Maxim A. Bastrakov ◽

Vadim V. Kachala ◽

Ivan V. Fedyanin ◽

Tatyana A. Klimova ◽

...

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group ◽

Chlorine Atom ◽

Simple Synthesis ◽

Smiles Rearrangement ◽

One Pot

AbstractA convenient process is described for the synthesis of novel thiazolo[4,5-b]pyridines fused with triazole or pyrimidine rings. The base-promoted reactions of 2-chloro-3-nitropyridines with 1,3-(S,N)-binucleophiles (triazole-5-thiols, 4-oxopyrimidine-2-thiones) resulted in nucleophilic substitution of the chlorine atom and subsequent S–N-type Smiles rearrangement followed by nucleophilic substitution of the nitro group. Reactions with pyrimidine-2-thiones were carried out as one-pot processes while, in the case of triazole-5-thiols, isolation of intermediate substitution products was found to be preferable.

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ChemInform Abstract: Nitropyrazoles. Part 19. Selective Nucleophilic Substitution of a Nitro Group in 3,4-Dinitropyrazoles.

ChemInform ◽

10.1002/chin.201125116 ◽

2011 ◽

Vol 42 (25) ◽

pp. no-no

Author(s):

I. L. Dalinger ◽

I. A. Vatsadze ◽

T. K. Shkineva ◽

I. O. Kortusov ◽

G. P. Popova ◽

...

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group

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Tandem of Nucleophilic Substitution of Hydrogen and Cyclocondensation with Participation of the Nitro Group in the Synthesis of Fluorine-Containing 3-Amino-1,2,4-benzotriazines.

ChemInform ◽

10.1002/chin.200717158 ◽

2007 ◽

Vol 38 (17) ◽

Author(s):

G. A. Zhumabaeva ◽

S. K. Kotovskaya ◽

N. M. Perova ◽

V. N. Charushin ◽

O. N. Chupakhin

Keyword(s):

Nucleophilic Substitution ◽

Nitro Group ◽

Nucleophilic Substitution Of Hydrogen

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METAMECONINE AS A MODEL COMPOUND IN THE STUDY OF AROMATIC REACTIONS

Canadian Journal of Chemistry ◽

10.1139/v62-364 ◽

1962 ◽

Vol 40 (12) ◽

pp. 2402-2408 ◽

Cited By ~ 2

Author(s):

S. Safe ◽

Marjorie Allen ◽

R. Y. Moir

Keyword(s):

Physical Properties ◽

Nucleophilic Substitution ◽

Nitro Group ◽

Model Compound ◽

Substitution Reactions ◽

Main Interest ◽

Nucleophilic Substitution Reactions ◽

Special Character ◽

Methylene Group

Previous work had shown the somewhat unexpected course of nitration, bromination, and demethylation reactions of metameconine and its derivatives. The discovery that metameconine could easily be dinitrated enabled us to bring to light equally interesting results in the relative rates of reduction of the nitro groups, in the course of certain nucleophilic substitution reactions, in the activation of the methylene group, and in certain physical properties. Much of the work, past and present, now holds as its main interest the somewhat special character of a nitro group in the 7-position.

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