Synthesis of glycofurano[2,1-d]imidazolidin-2-ones

Gonzalez, Martin Avalos; Moreno, P. C.; Monterrey, Isabel M. Gomez; Requejo, Jose L. Jimenez; Albarran, Juan C. Palacios; Vicente, F. Rebolledo; Mota, J. Fuentes

doi:10.1016/0008-6215(89)80051-5

Cited by 15 publications

(2 citation statements)

References 24 publications

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“…Also after 6 h, carbon signals between δ= 160 and 166.2 ppm were likewise visible and persisted over time. These can be assigned to isoureido groups present in heterocycles, as depicted in Schemes , , , and , and are consistent with related structures reported previously and observed in both D 2 O and organic solvents . It should be noted that C‐2 in d ‐ ribo ‐aminoxazoline 19 gives a 13 C NMR signal at δ= 166.0 ppm, whereas that of the C‐2 atom in diazaspiro‐bis‐oxazoline 20 appears at δ= 163.2 ppm .…”

Section: Resultssupporting

confidence: 88%

“…A distinctive feature from the other molar ratios is that signals attributable to glyoxal (between δ= 91 and 107 ppm) rapidly disappeared, including the intense one at δ= 93.2 ppm. Only a low intensity peak at δ= 102.9 ppm could be detected after 3 d. Four resonances in the range δ= 79–91 ppm, with the most intense peak at δ= 87.8 ppm as in the 1:1 mixture, were indicative of O−CHR−N fragments . It is noteworthy that, even working with excess cyanamide, a resonance unequivocally attributable to N−CHR−N bonds seldom emerged.…”

Section: Resultsmentioning

confidence: 94%

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Formation of Cyanamide–Glyoxal Oligomers in Aqueous Environments Relevant to Primeval and Astrochemical Scenarios: A Spectroscopic and Theoretical Study

Lavado¹,

Concepción²,

Babiano³

et al. 2018

Chemistry A European J

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The condensation of cyanamide and glyoxal, two well-known prebiotic monomers, in an aqueous phase has been investigated in great detail, demonstrating the formation of oligomeric species of varied structure, though consistent with generalizable patterns. This chemistry involving structurally simple substances also illustrates the possibility of building molecular complexity under prebiotically plausible conditions, not only on Earth, but also in extraterrestrial scenarios. We show that cyanamide-glyoxal reactions in water lead to mixtures comprising both acyclic and cyclic fragments, largely based on fused five- and six-membered rings, which can be predicted by computation. Remarkably, such a mixture could be identified using high-resolution electrospray ionization (ESI) mass spectrometry and spectroscopic methods. A few mechanistic pathways can be postulated, most involving the intermediacy of glyoxal cyanoimine and further chain growth, thus increasing the diversity of the observed products. This rationale is supported by theoretical analyses with clear-cut identification of all of the stationary points and transition-state structures. The properties and structural differences of oligomers obtained under thermodynamic conditions in water as opposed to those isolated by precipitation from organic media are also discussed.

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Section: Resultssupporting

confidence: 88%

Section: Resultsmentioning

confidence: 94%