Beilstein J. Org. Chem.2014,10, 2255–2262, doi:10.3762/bjoc.10.234
triaminoguanidinium salts underwent a threefold carbamoylation with aryl isocyanates to furnish 1,2,3-tris(ureido)guanidinium salts, while p-toluenesulfonyl isocyanate led only to a mono-ureido guanidinium salt. With aryl isothiocyanates, 3-hydrazino-1H-1,2,4-triazole-5(4H)-thione derivatives were obtained. Compounds
7a and 8 show interesting solid-state structures with intra- and intermolecular hydrogen bonds.
Keywords: aryl isocyanate; aryl isothiocyanate; carbamoylation; sulfonyl isocyanate; triaminoguanidinium salt; 1H-1,2,4-triazole-5(4H)-thione; Introduction
The 1,2,3-triaminoguanidinium ion, [C(NHNH2)3
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Graphical Abstract
Scheme 1:
Conditions: a) benzaldehyde, ethanol/water, reflux, 1 h, 96% yield; b) H2, Pd/C (10%), MeOH, rt, 48...