Recognition of a Single Guanine Bulge by 2-Acylamino-1,8-naphthyridine [J. Am. Chem. Soc. 2000, 122, 2172−2177].

Nakatani, Kazuhiko; Sando, Shinsuke; Saito, Isao

doi:10.1021/ja004667x

Cited by 22 publications

(31 citation statements)

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“…Quinolines and pyridines are an important class of heterocycles found in pharmaceuticals, agrochemicals and functional materials . Numerous synthetic protocols for the quinoline nucleus have been reported, including the Skraup, Comps, Conrad‐Limpach, Gould‐Jacobs, Doebner‐von Miller and Povarov reactions .…”

Section: Introductionmentioning

confidence: 99%

Phosphine Ligand‐Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

Guo

et al. 2019

ChemCatChem

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A series of phosphine‐free Ru(III)/Ru(II) complexes of NH functionalized N˄N˄N pincer ligands exhibit excellent activity for acceptorless dehydrogenative coupling (ADC) of secondary alcohols with 2‐aminobenzyl or γ‐amino alcohols to quinolines and pyridines. Ru(III) complexes [LRuCl3] (L=6‐(3‐R1,5‐R2‐1H‐pyrazol‐1‐yl)‐N‐(pyridin‐2‐yl)pyridin‐2‐amine; 1 a: R1=R2=H (L1); 1 b: R1=R2=Me (L2); 1 c: R1=H, R2=CF3 (L3); 1 d: R1=H, R2=Ph (L4); 1bMe: L=6‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐N‐methyl‐N‐(pyridin‐2‐yl)pyridin‐2‐amine (L2Me)) were obtained by refluxing RuCl3 ⋅ xH2O with the corresponding ligand in EtOH. Five Ru(II) complexes [LRu(DMSO‐κS)Cl2] (2 a: L=L1; 2 b: L=L2; 2 c: L=L3; 2 d: L=L4; 2bMe: L=L2Me) were formed by reducing the corresponding Ru(III) complex in refluxing EtOH. The latter complexes could also be prepared directly by refluxing Ru(DMSO)4Cl2 with the corresponding ligand in EtOH. These Ru(III) and Ru(II) complexes, especially 1 b/2 b, exhibited high catalytic efficiency and broad functional group tolerance in ADC reactions of secondary alcohols with 2‐aminobenzyl or γ‐amino alcohols to quinolines and pyridines. A detail mechanistic study indicated the Ru(III) complex was reduced into the Ru(II) species, which is the active catalytic center for ADC via a Ru−H/N−H bifunctional outer‐sphere mechanism. This protocol provides a reliable, atom‐economical and environmentally benign procedure for C−N and C−C bond formation.

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Section: Introductionmentioning

confidence: 99%

Phosphine Ligand‐Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

Guo

et al. 2019

ChemCatChem

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“…Naturally occurring nucleotides recognize their complementary nucleotide by forming multiple hydrogen bonds. Many synthetic molecules have been developed which use the similar recognition phenomenon to recognize nucleotides with higher selectivity ,. We have previously reported 2‐acylamino‐1,8‐naphthyridine derivatives which recognize oligonucleotide sequences containing guanine mismatches and bulges.…”

Section: Introductionmentioning

confidence: 99%

“…We have previously reported 2‐acylamino‐1,8‐naphthyridine derivatives which recognize oligonucleotide sequences containing guanine mismatches and bulges. Recognition was achieved through the complementary hydrogen bonding with unpaired guanine . There are previous reports for electrical detection of oligonucleotides containing G−G mismatched sequences in duplex or hairpin oligonucleotides using 2‐acylamino‐1,8‐naphthyridine dimers …”

Section: Introductionmentioning

confidence: 99%

Electrical Nucleotide Sensor Based on Synthetic Guanine‐Receptor‐Modified Electrodes

et al. 2018

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Methyl 2‐carbamate‐1,8‐naphthyridine thiophenolate derivative (NCTP) has been designed and synthesized, which can selectively bind to guanine derivatives. We immobilized NCTP on gold electrode and performed cyclic voltammetry analysis for guanosine sensing. The current blockage data obtained from these NCTP immobilized electrodes suggest that electrodes have higher selectivity for 2’‐deoxyguanosine monophosphate (dGMP) than 2’‐deoxythymidine monophosphate (dTMP), 2’‐deoxycytidine monophosphate (dCMP), and 2’‐deoxyadenosine monophophate (dAMP). Thus, synthetic reader molecule NCTP, which has complementary hydrogen bonding surface for guanine derivatives, could be useful for the sensing of guanosine mononucleotides and polynucleotides.

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“…As early as 1962, Eley and Spivey1 suggested that the unique DNA π stack may serve as a medium for charge transfer in this fundamental biopolymer. Currently, this remarkable DNA feature seems to be well documented through many experiments, which range from time‐resolved spectroscopic measurements2–4 to biochemical assays 5–8. The vital consequences of this phenomenon for biology and nanotechnology have not yet been completely comprehended, and current studies focus on these aspects rather than on acquiring further evidence for its existence.…”

Section: Introductionmentioning

confidence: 99%

Reduced Graphene Oxide as a Metal‐Free Carbocatalyst for Polymerization of 1‐Naphthylamine

et al. 2014

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Recognition of a Single Guanine Bulge by 2-Acylamino-1,8-naphthyridine [J. Am. Chem. Soc. 2000, 122, 2172−2177].

Cited by 22 publications

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Phosphine Ligand‐Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

Phosphine Ligand‐Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions

Electrical Nucleotide Sensor Based on Synthetic Guanine‐Receptor‐Modified Electrodes

Reduced Graphene Oxide as a Metal‐Free Carbocatalyst for Polymerization of 1‐Naphthylamine

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