Elsevier

Tetrahedron Letters

Volume 53, Issue 41, 10 October 2012, Pages 5523-5527
Tetrahedron Letters

1,3-Phenyl linked urea-based receptors for anions and the facile cyclization to imidazolidinedione

https://doi.org/10.1016/j.tetlet.2012.08.001Get rights and content

Abstract

Amino acid-based molecules containing a bis-urea moiety have been synthesized and demonstrated for their anion binding affinities. Compound 1c binds phosphate and sulfate with binding constants of 3.6 × 103 M−1 and 4.3 × 103 M−1, respectively. These molecules undergo proton transfer upon treatment with fluoride, resulting in the formation of imidazolidinediones. The crystal structure of one such diimidazolidinedione displays self-assembly through nonconventional hydrogen bonding interactions.

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Acknowledgments

We thank the Department of Science and Technology (DST), New Delhi for the financial assistance. DST-FIST and IIT Delhi for the HRMS facilities. CDRI, Lucknow for the mass spectrometric analysis. IIT Delhi and IIT Bombay for single crystal XRD.

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