Synthesis and Application of Thiosquaramides and Their Derivatives: A Review

  • Sándor Nagy Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary https://orcid.org/0000-0001-6251-5382
  • Péter Kisszékelyi Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary https://orcid.org/0000-0002-9529-0674
  • József Kupai Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary http://orcid.org/0000-0002-4212-4517

Abstract

Thiosquaramides are the thio analogues of squaramides that are widely applicable in the fields of asymmetric catalysis, pharmaceutical research, and chemical biology. Having four-membered ring system derived from squaric acid, thiosquaramides are feasible hydrogen bond donors and acceptors. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. In this review the structural properties, acidity, and lipophilicity of thiosquaramides and squaramides are compared. Different synthetic procedures starting from squarates, half-squaramides or squaramides are shown, and the main derivatization methods are outlined. Finally, the yet only few applications of this interesting family are reviewed. Considering their hydrogen bonding and aromatic switching, in combination with structural rigidity, they bear the possibility of becoming robust and tunable bifunctional organocatalysts for a range of synthetically useful transformations in the future.

Keywords: thiosquaramide, squaramide, hydrogen bond donors, organocatalysis, anion transport
Published online
2018-11-05
How to Cite
Nagy, S., Kisszékelyi, P. and Kupai, J. (2018) “Synthesis and Application of Thiosquaramides and Their Derivatives: A Review”, Periodica Polytechnica Chemical Engineering, 62(4), pp. 467–475. doi: https://doi.org/10.3311/PPch.12851.
Section
Articles