Download PDF
Synthesis 2003(18): 2851-2857  
DOI: 10.1055/s-2003-42458
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue

Aleksandr V. Golovchenkoa, Stepan G. Pilyoa, Vladimir S. Brovarets*a, Alexander N. Chernegab, Boris S. Dracha
a Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska str. 1, Kyiv-94, 02094, Ukraine
Fax: +380(44)5732561; e-Mail: Drach@bpci.kiev.ua;
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska str. 5, Kyiv-94, 02094, Ukraine
Fax: +380(44)5732643;
Further Information

Publication History

Received 23 July 2003
Publication Date:
04 November 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

The adducts formed by 4-functionally-substituted 2-aryl-5-hydrazino-1,3-oxazoles and aryl isothiocyanates recyclize on heating to produce the hitherto unknown derivatives of (1,3,4-thiadiazol-2-yl)glycine and its phosphonyl analogue.

Key words

α-aminocarboxylic acids - α-aminoalkylphosphonic acids - (1,3,4-thiadiazol-2-yl)glycine - 1,3-oxazoles - 3,3-dichloroacrylates - 2,2,2-trichloroethylphosphonates - aryl isothiocyanates

    References

  • 1 Adlington RM. Baldwin JE. Catteric D. Pritchard GJ. J. Chem. Soc., Perkin Trans. 1  1999,  855 
    CrossrefGoogle Scholar
  • 2 Adlington RM. Baldwin JE. Catteric D. Pritchard GJ. J. Chem. Soc., Perkin Trans. 1  2000,  299 
    CrossrefGoogle Scholar
  • 3 Jones RCF. Berthelot DJC. Iley JN. Chem. Commun.  2000,  2131 
    CrossrefGoogle Scholar
  • 4 Adlington RM. Baldwin JE. Catteric D. Pritchard GJ. Tang LT. J. Chem. Soc., Perkin Trans. 1  2000,  2311 
    CrossrefGoogle Scholar
  • 5 Adlington RM. Baldwin JE. Catteric D. Pritchard GJ. J. Chem. Soc., Perkin Trans. 1  2001,  668 
    CrossrefGoogle Scholar
  • 6 Stensbol TB. Uhlmann P. Morel S. Eriksen BL. Felding J. Kromann H. Hermit MB. Greenwood TR. Bräuner-Osborne H. Madsen U. Junager F. Krogsgaard-Larsen P. Begtrup M. Vedso P. J. Med. Chem.  2002,  45:  19 
    CrossrefGoogle Scholar
  • 7 Myers AG. Gleason JL. J. Org. Chem.  1996,  61:  813 
    CrossrefGoogle Scholar
  • 8 Whitlock BJ. Lipton SH. Strong FM. J. Org. Chem.  1965,  30:  115 
    CrossrefGoogle Scholar
  • 9 Eugster H. Müller GFR. Good R. Tetrahedron Lett.  1965,  1813 
    CrossrefGoogle Scholar
  • 10 Matzen L. Engesgaard A. Ebert B. Didriksen M. Frolund B. Krogsgaard-Larsen P. Jaroszewski JW. J. Med. Chem.  1997,  40:  520 
    CrossrefGoogle Scholar
  • 11a Lunn WHW. Schoepp DD. Lodge D. True RA. Millar JD. Book of Abstracts, 12th International Symposium on Medicinal Chemistry, Basel, Switzerland, September 13-17, 1992   Swiss Chemical Society; Basel: 1992.  p.P-041 
    Google Scholar
  • 11b Lunn WHW. Schoepp DD. Lodge D. True RA. Millar JD. Book of Abstracts, 12th International Symposium on Medicinal Chemistry, Basel, Switzerland, September 13-17, 1992   Swiss Chemical Society; Basel: 1992.  p.A-040 
    Google Scholar
  • 12 Drach BS. Miskevich GN. Zh. Org. Khim.  1974,  10:  2315 ; Chem. Abstr. 1975, 82, 72843
    Google Scholar
  • 13 Matsumura K. Saraie T. Hashimoto N. Chem. Pharm. Bull.  1976,  24:  924 
    CrossrefGoogle Scholar
  • 14 Pilyo SG. Brovarets VS. Vinogradova TK. Chernega AN. Drach BS. Zh. Obshch. Khim.  2001,  71:  310 
    Google Scholar
  • 15 Boulton AJ. Katritzky AR. Hamid AM. J. Chem. Soc. C  1967,  2005 
    CrossrefGoogle Scholar
  • 16 Brovarets VS. Vydzhak RN. Pilyo SG. Zyuz KV. Drach BS. Zh. Obshch. Khim.  2001,  71:  1822 
    Google Scholar
  • 17 Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity   Kukhar VP. Hudson HR. Wiley; Chichester: 2000. 
    Google Scholar
  • 18 Boduszek B. Phosphorus, Sulfur Silicon Relat. Elem.  1995,  104:  63 
    CrossrefGoogle Scholar
  • 19 Boduszek B. Phosphorus, Sulfur Silicon Relat. Elem.  1996,  113:  209 
    CrossrefGoogle Scholar
  • 20 Boduszek B. Tetrahedron  1996,  52:  12483 
    CrossrefGoogle Scholar
  • 21 Cottier L. Descotes G. Gonera G. Grabowski G. Levkowski J. Skowronski R. Phosphorus, Sulfur Silicon Relat. Elem.  1996,  118:  181 
    CrossrefGoogle Scholar
  • 22 Journet M. Cai D. Larson RD. Reider PJ. Tetrahedron Lett.  1998,  39:  1717 
    CrossrefGoogle Scholar
  • 23 North ACT. Phillips DC. Mathews FS. Acta Crystallogr., Sect. A  1968,  24:  351 
    CrossrefGoogle Scholar
  • 24 Watkin DJ. Prout CK. Carruthers JR. Betteridge PW. CRYSTALS   Issue 10:  Chemical Crystallography Laboratory, University of Oxford; Oxford: 1996. 
    Google Scholar
  • 25 Carruthers JR. Watkin DJ. Acta Crystallogr., Sect. A  1979,  35:  698 
    CrossrefGoogle Scholar
26

Full crystallographic details have been deposited at Cambridge Crystallographic Data Centre (CCDC). Any request to the CCDC for this material, should quote the full literature citation and reference number CCDC 215589.