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

作者：Szabo Jan; Karger Kerstin; Bucher Nicolas; Maas Gerhard^*

来源：Beilstein Journal of Organic Chemistry, 2014, 10: 2255-2262.

DOI：10.3762/bjoc.10.234

• aryl isocyanate
• aryl isothiocyanate
• carbamoylation
• sulfonyl isocyanate
• triaminoguanidinium salt
• 1H-1,2,4-triazole-5(4H)-thione

1,2,3-Triaminoguanidinium chloride was combined with benzaldehyde and hydratropic aldehyde to furnish the corresponding tris(imines), which were converted into 1,2,3-tris(benzylamino) guanidinium salts by catalytic hydrogenation in the former, and by borane reduction in the latter case. The resulting alkyl-substituted 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.

• 出版日期2014-9-24