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Beilstein J. Org. Chem. 2014, 10, 2255–2262, doi:10.3762/bjoc.10.234
Graphical Abstract
Scheme 1: Conditions: a) benzaldehyde, ethanol/water, reflux, 1 h, 96% yield; b) H2, Pd/C (10%), MeOH, rt, 48...
Scheme 2: Carbamoylation of 1,2,3-tris(benzylamino)guanidinium salts 3 and 5-OTs.
Figure 1: Solid-state structure of 7a·3CH3CN. Left: Molecular structure with numbering of atoms. Right: N–H··...
Scheme 3: Deprotonation of 7a to yield the neutral guanidine derivative 8.
Figure 2: Solid-state structure of 8. Thermal displacement ellipsoids are drawn at the 20% probability level....
Scheme 4: Sulfonylcarbamoylation of salt 3.
Figure 3: Hydrogen-bonded one-dimensional network of guanidine 8 in the solid state. The intramolecular N9···...
Scheme 5: Reaction of 1,2,3-trisbenzylaminoguanidinium chloride (3) with aryl isothiocyanates.
Figure 4: Solid-state structure of 10b. Thermal displacement ellipsoids are drawn at the 30% probability leve...
Scheme 6: Proposed mechanism of the formation of 10 and 11.