Direct Functionalization of C–H Fragments in Nitroarenes as a Synthetic Pathway to Condensed N-Heterocycles

Шевелев, С. А.; Старосотников, А. М.

doi:10.1007/7081_2013_112

Cited by 6 publications

(2 citation statements)

References 137 publications

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“…Recently, aromatic substrates (including heterocycles) have been reported to undergo [3+2]-cycloaddition by C=C bonds as dipolarophiles with azomethine ylides providing annulation of the pyrrolidine, pyrroline or pyrrole rings. [7][8][9][10] The present work extends our ongoing research [11][12][13][14][15][16] on the application of the dearomatization methodology to the synthesis of novel nitrogen-oxygen systems 17,18 -potential NO donors containing two or more pharmacophoric fragments. Since the 1980s, when the unique role of NO in the regulation of numerous physiological and pathophysiological processes was discovered, this small molecule has been of exceptional interest.…”

Section: Introductionsupporting

confidence: 53%

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

Bastrakov¹,

Kucherova²,

Fedorenko³

et al. 2017

Arkivoc

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An efficient and convenient one-step method for the synthesis of decahydrodipyrrolo [3,4-b:3',4'-d]pyridine derivatives was developed on the basis of 1,3-dipolar cycloaddition of unstabilized N-methyl azomethine ylide with 2-substituted 3,5-dinitropyridines. This novel heterocyclic system contains two 3-nitropyrrolidine fragments fused to a partially saturated pyridine ring. Such types of compound, as follows from the literature, can be considered as potential nitric oxide donors.

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Section: Introductionsupporting

confidence: 53%

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

Bastrakov¹,

Kucherova²,

Fedorenko³

et al. 2017

Arkivoc

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“…These carbazoles were obtained in a fully regioselective fashion via a three-component reaction that generates four new bonds and two rings from 2-nitrochalcones 1 , primary amines 2 and β-dicarbonyl compounds 3 (Scheme b). Besides being, to our knowledge, the first multicomponent synthesis of carbazole derivatives, the method includes the functionalization of a C–H group by direct attack onto a nitrogen function, a transformation that is very rare in contrast to the direct functionalization of C–H fragments in the ortho -position relative to the nitro group of nitroarenes …”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Functionalized Carbazoles via a CAN-Catalyzed Multicomponent Process Comprising a C–H Activation Step

et al. 2017

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The microwave-promoted three-component reaction between o-nitrochalcones, primary amines and β-dicarbonyl compounds in the presence of Ce(IV) ammonium nitrate constitutes the first example of a multicomponent carbazole synthesis. This reaction furnishes highly substituted and functionalized carbazole derivatives via a double annulation process that generates two C-C and two C-N bonds, with water as the only side product. Mechanistically, this transformation has some unusual features that include an intramolecular coupled hydrogenation-dehydrogenation process, the functionalization of a C-H group by direct attack onto a nitrogen function and a CAN-catalyzed reduction via hydride transfer from ethanol. The mechanisms of these reactions were studied with the aid of computational techniques.

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Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines

et al. 2019

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Facile and efficient protocols for the synthesis of 2- R-6,8-dinitro [1,2,4]triazolo[1,5-a]pyridines from commercially available starting materials have been developed. The reactions proceed via cyclization of corresponding 3,5-dinitropyridine-2-yl hydrazides or aldehyde 3,5-dinitropyridine-2-yl hydrazones followed by in situ Dimroth rearrangement to provide these triazole fused bicyclic heterocycles in good yields under mild conditions. Another synthetic route to target N-bridged dinitro [1,2,4] triazolo [1,5-a]pyridines includes arylation of 5-aryltetrazoles with 2-chloro-3,5-dinitropyridine and subsequent thermal decomposition/cyclization.

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Direct Functionalization of C–H Fragments in Nitroarenes as a Synthetic Pathway to Condensed N-Heterocycles

Cited by 6 publications

References 137 publications

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

Dearomatization of 3,5-dinitropyridines – an atom-efficient approach to fused 3-nitropyrrolidines

One-Pot Synthesis of Functionalized Carbazoles via a CAN-Catalyzed Multicomponent Process Comprising a C–H Activation Step

Synthesis of N‐Bridged 6,8‐Dinitrotriazolo[1,5‐a]pyridines

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