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Szabo J, Karger K, Bucher N, et al. Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates. Beilstein J Org Chem. 2014;10:2255-62doi: 10.3762/bjoc.10.234.
Szabo, J., Karger, K., Bucher, N., & Maas, G. (2014). Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates. Beilstein journal of organic chemistry, 102255-62. https://doi.org/10.3762/bjoc.10.234
Szabo, Jan, et al. "Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates." Beilstein journal of organic chemistry vol. 10 (2014): 2255-62. doi: https://doi.org/10.3762/bjoc.10.234
Szabo J, Karger K, Bucher N, Maas G. Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates. Beilstein J Org Chem. 2014 Sep 24;10:2255-62. doi: 10.3762/bjoc.10.234. eCollection 2014. PMID: 25298792; PMCID: PMC4187099.
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Beilstein J Org Chem. 2014 Sep 24;10:2255-62. doi: 10.3762/bjoc.10.234. eCollection 2014.

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

Beilstein journal of organic chemistry

Jan Szabo, Kerstin Karger, Nicolas Bucher, Gerhard Maas

Affiliations

  1. Institute of Organic Chemistry I, University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany.
  2. Institute of Organic Chemistry I, University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, Germany, ; (new address) TUM CREATE, Singapore 138602, Singapore.

PMID: 25298792 PMCID: PMC4187099 DOI: 10.3762/bjoc.10.234

Abstract

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.

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

References

  1. Chemistry. 2005 May 20;11(11):3318-24 - PubMed
  2. Angew Chem Int Ed Engl. 2011 Apr 26;50(18):4227-9 - PubMed
  3. Chem Asian J. 2012 Jan 2;7(1):214-24 - PubMed
  4. Pharmazie. 1977 Aug-Sep;32(8-9):458-60 - PubMed

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