Photochemistry of N-acylimino-isoquinolinium and -quinolinium betaines

Tamura, Yasumitsu; Matsugashita, Saeko; Ishibashi, Hiroki; Ikeda, Masazumi

doi:10.1016/s0040-4020(01)93363-0

Cited by 29 publications

(15 citation statements)

References 23 publications

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“…Salts VIIIa-VIIIc, VIIIe-VIIIi, IX-XII, and XIV were reported previously [21][22][23][24][25][26][27][28][29][30][31]. The structure of salts VIIId, VIIIj, and XIII was confirmed by comparing their 1 H and 13 C NMR spectra with those of structurally related compounds [13,[21][22][23][24].…”

Section: Methodssupporting

confidence: 55%

Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds

2011

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Relative rates of the amination of 3-X-and 4-X-substituted pyridines (X = H, 3-Me, 4-Me, 3-F 3 C, 3-CN, 4-CN, 3-Cl, 3-Br, 4-MeO, 4-Me 2 N), pyrazine, quinoline, isoquinoline, 2,2′-and 4,4′-bipyridines, and 1,10-phenanthroline with O-mesitylenesulfonylhydroxylamine were estimated by NMR spectroscopy. Correlations were found between logarithms of the relative amination rate constants and substituent constants σ or σ I and σ R for X-substituted pyridines. A wide series of nitrogen-containing heterocyclic compounds turned out to fit correlations between logarithms of the relative amination rate constants, on the one hand, and relative stabilities of N-aminoazinium cations, energies of activation of the amination process, and gas-phase proton affinities, calculated by the DFT/PBE/3z and DFT/B3LYP/L2 methods, on the other.

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Section: Methodssupporting

confidence: 55%

Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds

2011

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“…and MSH (1 equiv.) at 0 °C afforded the N-aminated salt 4f [32][33][34] as a precipitate in 82% yield. The long reaction time (3 h) was attributed to the low basicity of 3f (pK aH in MeCN: 12.0).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of <i>N</i>-Aminated Salts of Aliphatic <i>tert</i>-Amines, (Trialkyl)amidines, and (Pentaalkyl)guanidines by Electrophilic Amination in an Ethereal Solvent

Fujita

Arai

Kunishima

2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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The electrophilic amination of nitrogen-based nucleophiles, including strong organic bases, was conducted in an Et 2 O solvent using O-(mesitylenesulfonyl)hydroxylamine. Aliphatic tert-amines and N,N,N′-(trialkyl) amidines rapidly formed precipitates of the corresponding aminated salts in high yields. The amination of the highly basic and sterically hindered N,N,N′,N′,N″-(pentaalkyl)guanidines was achieved under modified conditions, although the yields were moderate because of a competing side reaction caused by the acid-base equilibrium.

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“…The 1-aminopyridinium salts (41) required for this reaction were prepared by treating a pyridine with either hydroxylamine-O-sulfonic acid (90), hydroxylamine-O-mesitylenesulfonate (160,164), or hydroxylamine-0-2,4-dinitrophenyl ether (121). This amination occurred with other nitrogen heterocycles (166) such as isoquinoline (161), quinoline, phenanthridine (7,61), acridines (6), and pyridazine (86) and also with aliphatic tertiary amines and alkaloids (165). The use of A^-tosylhydroxylamine in the presence of phosphorus pentoxide converted pyridine directly to pyridine-l-tosylamine (127).…”

Section: Introductionmentioning

confidence: 99%

Chemistry of Aminimides

Wawzonek¹

1980

Ind. Eng. Chem. Prod. Res. Dev.

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The period 1972-1979 saw considerable activity in research of the chemistry and utilization of aminimides. Studies have extended investigation to aminimides in which the acyl group is derived from imino acids, cyanuric acid, phosphonic acids, and picric acid and to vinylogues of aminimides. Work continued with aminimides derived from nitrogen heterocycles and their conversion to diazepines and bridged nitrogen bicyclic compounds. Commercial utilization of aminimides based on 1,1dimethylhydrazine has been hampered in this country by the loss of the sole commercial source of this compound.

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Photochemistry of N-acylimino-isoquinolinium and -quinolinium betaines

Cited by 29 publications

References 23 publications

Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds

Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds

Synthesis of <i>N</i>-Aminated Salts of Aliphatic <i>tert</i>-Amines, (Trialkyl)amidines, and (Pentaalkyl)guanidines by Electrophilic Amination in an Ethereal Solvent

Chemistry of Aminimides

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