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Synthesis and Crystal Structure Determination of Hydantoin-l-Proline

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Abstract

The title compound, hydantoin-l-proline, C6H8N2O2, crystallize in the orthorhombic system with space group P212121 (N°19), Z = 4, and unit cell parameters a = 7.136(1) Å, b = 8.009(2) Å, c = 11.378(2) Å. The molecular structure shows a hydantoin and pyrrolidine ring coupling forming a bicyclohydantoin. The crystal packing is governed by N–H···O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains.

Graphical Abstract

In the crystal structure of hydantoin-l-proline, a bicyclohydantoin, the molecules are linked by N–H···O hydrogen bonds, forming infinite one-dimensional zigzag chains, running along [010] plane, with a C(4) graph-set motif.

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References

  1. López CA, Trigo GG (1985) Adv Heterocycl Chem 38:177

    Article  Google Scholar 

  2. Meusel M, Gütschow M (2004) Org Prep Proced Int 36:391

    Article  CAS  Google Scholar 

  3. Park KH, Ehrler J, Spoerri H, Kurth MJ (2001) J Comb Chem 3:171

    Article  CAS  Google Scholar 

  4. Lin MJ, Sun CM (2003) Tetrahedron Lett 44:8739

    Article  CAS  Google Scholar 

  5. Zhang W, Lu YM, Chen CHT, Zeng L, Kassel DB (2006) J Comb Chem 8:687

    Article  CAS  Google Scholar 

  6. Mutschler E, Derendorf H (1995) Drug actions, basic principles and therapeutic aspects. Medpharm Scientific Publishers, Stuttgart

    Google Scholar 

  7. Dylag T, Zygmunt M, Maciag D, Handzlik J, Bednarski M, Filipek B, Kiec-Kononowicz K (2004) Eur J Med Chem 39:1013

    Article  CAS  Google Scholar 

  8. Opacic N, Barbaric M, Zorc B, Cetina M, Nagy A, Frkovic D, Kralj M, Pavelic K, Balzarini J, Andrei G, Snoeck R, Declercq E, Raic-Malic S, Mintas M (2005) J Med Chem 48:475

    Article  CAS  Google Scholar 

  9. Lattmann E, Ayuko WO, Kinchinaton D, Langley CA, Singh H, Karimi L, Tisdale MJ (2003) J Pharm Pharmacol 55:1259

    Article  CAS  Google Scholar 

  10. Carmi C, Cavazzoni A, Zuliani V, Lodola A, Bordi F, Plazzi PV, Alfieri RR, Petronini PG, Mor M (2006) Bioorg Med Chem Lett 16:4021

    Article  CAS  Google Scholar 

  11. Singh G, Driever PH, Sander JW (2005) Brain 128:7

    Article  Google Scholar 

  12. Merrit HH, Putnam TJ (1938) Schweiz Arch Neurol Psychiatr 39:1003

    Google Scholar 

  13. Shiozaki M (2002) Carbohydr Res 337:2077

    Article  CAS  Google Scholar 

  14. Marton J, Enisz J, Hosztafi S, Timár T (1993) J Agric Food Chem 41:148

    Article  CAS  Google Scholar 

  15. Wilms B, Wiese A, Syldatk C, Mattes R, Altenbuchner J (2001) J Biotechnol 86:19

    Article  CAS  Google Scholar 

  16. Burton SG, Dorrington RA (2004) Tetrahedron Asymmetry 15:2737

    Article  CAS  Google Scholar 

  17. Kleinpeter E (1997) Struct Chem 2:161

    Article  Google Scholar 

  18. Ganesan A (2003) Methods Enzymol 369:415

    Article  CAS  Google Scholar 

  19. Vázquez J, Royo M, Albericio F (2004) Lett Org Chem 1:224

    Article  Google Scholar 

  20. Alsina J, Scott WL, O’Donnell MJ (2005) Tetrahedron Lett 46:3131

    Article  CAS  Google Scholar 

  21. Kumar V, Rana H, Sankolli R, Kaushik MP (2011) Tetrahedron Lett 52:6148

    Article  CAS  Google Scholar 

  22. Seijas LE, Delgado GE, Mora AJ, Bahsas A, Uzcategui J (2006) Av Quím 1:3

    Google Scholar 

  23. Seijas LE, Delgado GE, Mora AJ, Bahsas A, Briceño A (2007) Acta Cryst C63:o303

    CAS  Google Scholar 

  24. Delgado GE, Mora AJ, Uzcátegui J, Bahsas A, Briceño A (2007) Acta Cryst C63:o448

    CAS  Google Scholar 

  25. Seijas LE, Mora AJ, Delgado GE, Brunelli M, Fitch AN (2010) Powder Diffr 25:342

    Article  CAS  Google Scholar 

  26. Delgado GE, Seijas LE, Mora AJ, González T, Briceño A (2012) J Chem Crystallogr 42:388

    Article  CAS  Google Scholar 

  27. Rigaku (2002) CrystalClear. Rigaku Corporation, Tokyo

    Google Scholar 

  28. Rigaku MSC (2004) Crystal structure. Rigaku/MSC, The Woodlands

    Google Scholar 

  29. Sheldrick GM (2008) Acta Cryst A64:112

    CAS  Google Scholar 

  30. Flack HD (1983) Acta Cryst A39:876

    CAS  Google Scholar 

  31. Brandenburg K (1998) DIAMOND. Crystal Impact GbR, Bonn

    Google Scholar 

  32. Yu FL, Schwalbe CH, Watkin DJ (2004) Acta Cryst C60:o714

    CAS  Google Scholar 

  33. Allen FH (2002) Acta Cryst B58:380

    CAS  Google Scholar 

  34. Arte E, Tinant B, Declercq J, Germain G, van Meerssche M (1980) Bull Soc Chim Belg 89:379

    Article  CAS  Google Scholar 

  35. Griffin JF, Duax W, Weeks M (1984) Atlas of steroid structure. Plenum Publishing Corporation, New York

    Book  Google Scholar 

  36. Etter MC (1990) Acc Chem Res 23:120

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by CDCHT-ULA (Grant C-1755-11-08-B) and FONACIT (Grant LAB-97000821). The authors also thank to MSc. Teresa González and Dr. A. Briceño, IVIC, Venezuela, for data collection.

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Authors and Affiliations

  1. Laboratorio de Cristalografía, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes, Mérida, 5101, Venezuela

    Gerzon E. Delgado, Luis E. Seijas & Asiloé J. Mora

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  1. Gerzon E. Delgado
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  2. Luis E. Seijas
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  3. Asiloé J. Mora
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Correspondence to Gerzon E. Delgado.

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Delgado, G.E., Seijas, L.E. & Mora, A.J. Synthesis and Crystal Structure Determination of Hydantoin-l-Proline. J Chem Crystallogr 42, 968–971 (2012). https://doi.org/10.1007/s10870-012-0344-3

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  • DOI: https://doi.org/10.1007/s10870-012-0344-3

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