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2 article(s) from Szabo, Jan

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

Jan Szabo,
Julian Greiner and
Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

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Scheme 1: Reactions of aminoguanidines with carboxylic acids and acid chlorides. The structural formulae show...

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Scheme 2: Threefold N-acylation of triaminoguanidinium chloride (1) with acyl chloride 2b.

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Scheme 3: Reaction of 1,2,3-tris(benzylamino)guanidinium salts 4 and 5 with acyl chlorides to give 1,2,3-tris...

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Figure 1: Molecular structure of 6b·2C₂H₅OH in the solid state, with numbering of atoms (ORTEP plot). Selecte...

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Scheme 4: Protonation and methylation of 1,2,4-triazolium-3-aminides 7b,c.

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Scheme 5: Catalytic hydrogenation/debenzylation of betaines 7.

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Figure 2: Left: molecular structure of 8b in the solid state (OLEX2 plot). Right: crystal structure viewed al...

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Figure 3: Left: solid-state structure of 9b·H₂O (ORTEP plot). Right: centrosymmetric hydrogen-bonded dimer of...

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Figure 4: Solid-state structure of mesoionic compound 7a (ORTEP plot); thermal displacement ellipsoids are dr...

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Figure 5: UV–vis spectra of 7a–d in chloroform (c = 0.04 mmol L⁻¹); λ_max [nm] (ε [L mol⁻¹ cm⁻¹]): 7a: 350 (47...

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Published 22 Mar 2017

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Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates

Jan Szabo,
Kerstin Karger,
Nicolas Bucher and
Gerhard Maas

Beilstein J. Org. Chem. 2014, 10, 2255–2262, doi:10.3762/bjoc.10.234

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Scheme 1: Conditions: a) benzaldehyde, ethanol/water, reflux, 1 h, 96% yield; b) H₂, Pd/C (10%), MeOH, rt, 48...

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Scheme 2: Carbamoylation of 1,2,3-tris(benzylamino)guanidinium salts 3 and 5-OTs.

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Figure 1: Solid-state structure of 7a·3CH₃CN. Left: Molecular structure with numbering of atoms. Right: N–H··...

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Scheme 3: Deprotonation of 7a to yield the neutral guanidine derivative 8.

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Figure 2: Solid-state structure of 8. Thermal displacement ellipsoids are drawn at the 20% probability level....

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Scheme 4: Sulfonylcarbamoylation of salt 3.

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Figure 3: Hydrogen-bonded one-dimensional network of guanidine 8 in the solid state. The intramolecular N9···...

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Scheme 5: Reaction of 1,2,3-trisbenzylaminoguanidinium chloride (3) with aryl isothiocyanates.

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Figure 4: Solid-state structure of 10b. Thermal displacement ellipsoids are drawn at the 30% probability leve...

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Scheme 6: Proposed mechanism of the formation of 10 and 11.

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Published 24 Sep 2014

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