2003
DOI: 10.1002/ejoc.200390147
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Bis‐Aminals of Linear Tetraamines: Kinetic and Thermodynamic Aspects of the Condensation Reaction

Abstract: The kinetic and thermodynamic aspects of the condensation reaction of dicarbonyl compounds with linear tetraamines were examined in the light of identification of intermediates and DFT calculations.

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Cited by 26 publications
(20 citation statements)
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“…The structures of novel compounds were characterized by a combination of 1 H NMR, 13 C NMR, IR, UV-vis, elemental analysis and MS spectral data. 3,3 0 -Piperazine-1,4-diyldipropan-1-amine 1 [25], 1,2-dichloro-4,5-dicyanobenzene 4 [26] were prepared according to the literatures (Fig. 1).…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…The structures of novel compounds were characterized by a combination of 1 H NMR, 13 C NMR, IR, UV-vis, elemental analysis and MS spectral data. 3,3 0 -Piperazine-1,4-diyldipropan-1-amine 1 [25], 1,2-dichloro-4,5-dicyanobenzene 4 [26] were prepared according to the literatures (Fig. 1).…”
Section: Resultsmentioning
confidence: 99%
“…3,3 0 -Piperazine-1,4-diyldipropan-1-amine 1 [25], 1,2-dichloro-4,5-dicyanobenzene 4 [26] were prepared according to the literatures. All reagents and solvents were of reagent grade quality and were obtained from commercial suppliers.…”
Section: Methodsmentioning
confidence: 99%
“…The 1 H NMR spectrum (Figure 1) has been recorded in the presence of two inequivalent protons at δ 6.63 and 6.75, corresponding to hydrogen born by the aromatic ring (positions 6 and 7). On the other hand, three broad singlets at δ 5.09, 5.32 and 7.65 are attributed to NH 2 and NH protons (positions 8, 9 and 2.25 and 4.16 correspond to the bridging propyl and ethyl moieties (positions 1 signal integration corresponding to two protons.A tentative mechanism of formation of compound 2 is proposed in aminals from glyoxal and polyamines [22,23]. Next, to assess the reactivity of the amine functions in compound 2, it was further condensed to p quinoxalinium derivative 3 with 90% yield (Scheme 4).…”
Section: Methodsmentioning
confidence: 99%
“…Therefore, an isomerization of the aminals derived from open-chain amines was carefully investigated [149][150][151][152]. An additional key reaction is deprotection.…”
Section: Synthesis Of Cyclenmentioning
confidence: 99%