PDF icon PDF herunterladen
Synthesis 2012(4): 547-550  
DOI: 10.1055/s-0031-1289673
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Benzoxazines, Quinazolines and 4H-Benzo[e][1,3]thiazine by ANRORC Rearrangements of 1,2,4-Oxadiazoles

Bogdan Draghicia, Bahaa El-Dien M. El-Gendya,b, Alan R. Katritzky*a,c
a Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
b Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt
c Department of Chemistry, King Abdulaziz University, Jeddah 21589, Saudi Arabia
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
Weitere Informationen

Publikationsverlauf

Received 20 October 2011
Publikationsdatum:
23. Januar 2012 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

1,2,4-Oxadiazoles undergo ANRORC (addition of nucleophile, ring-opening and ring-closure) rearrangements upon reaction with excess of n-butyllithium to give benzoxazines, benzothiazines, and quinazolines in good yields under mild conditions.

Key words

N,O-heterocycles - rearrangements - benzoxazines - quinazolines - benzothiazines

    References

  • 1a Bird CW. Tetrahedron  1985,  41:  1409 
    Suche in Google Scholar
  • 1b Bird CW. Tetrahedron  1992,  48:  335 
    Suche in Google Scholar
  • 2a Macor JE. Ordway T. Smith RL. Verhoest PR. Mack RA. J. Org. Chem.  1996,  61:  3228 
    Suche in Google Scholar
  • 2b Angelini F. inventors; PCT GB  924608.  ; Chem. Abstr. 1963, 59, 35652
  • 2c Ledniczky L, and Seres I. inventors; PCT Int. Appl. WO  199904822.  ; Chem. Abstr. 1999, 130, 172993
  • 2d Pibiri I. Pace A. Palumbo Piccionello A. Pierro P. Buscemi S. Heterocycles  2006,  68:  2653 
    Suche in Google Scholar
  • 2e Torgova SI. Karamysheva LA. Geivandova TA. Strigazzi A. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A  2001,  365:  99 
    Suche in Google Scholar
  • 2f Taguchi T. inventors; Jpn. Kokai Tokkyo Koho;  US6451457. 
  • 3a Boulton AJ. Katritzky AR. Hamid AM. J. Chem. Soc. C  1967,  2005 
  • 3b Afridi AS. Katritzky AR. Ramsden CA. J. Chem. Soc., Perkin Trans. 1  1976,  315 
  • 3c Peña-Gallego A. Rodríguez-Otero J. Cabaleiro-Lago EM. J. Org. Chem.  2004,  69:  7013 
    Suche in Google Scholar
  • 3d D’Anna F. Frenna V. Lanza CZ. Macaluso G. Marullo S. Spinelli D. Spisani R. Petrillo G. Tetrahedron  2010,  66:  5442 
    Suche in Google Scholar
  • 3e Jochims JC. In Comprehensive Heterocycle Chemistry II   2nd ed., Vol. 4:  Rees CW. Katritzky AR. Scriven EFV. Pergamon; Oxford: 1996.  p.179 
    Suche in Google Scholar
  • 3f Pace A. Pierro P. Org. Biomol. Chem.  2009,  7:  4337 
    Suche in Google Scholar
  • 3g Hemming K. In Comprehensive Heterocyclic Chemistry III   3rd ed., Vol. 5:  Katritzky AR. Ramsden CA. Scriven EFV. Taylor RJK. Elsevier; London: 2008.  p.243 
    Suche in Google Scholar
  • 4a Buscemi S. Pace A. Pibiri I. Vivona N. Spinelli D. J. Org. Chem.  2003,  68:  605 
    Suche in Google Scholar
  • 4b Buscemi S. Pace A. Pibiri I. Vivona N. Lanza CZ. Spinelli D. Eur. J. Org. Chem.  2004,  974 
  • 4c Buscemi S. Pace A. Palumbo Piccionello A. Pibiri I. Vivona N. Giorgi G. Mazzanti A. Spinelli D. J. Org. Chem.  2006,  71:  8106 
    Suche in Google Scholar
  • 4d Buscemi S. Pace A. Palumbo Piccionello A. Macaluso G. Vivona N. Spinelli D. Giorgi G. J. Org. Chem.  2005,  70:  3288 
    Suche in Google Scholar
  • 4e Palumbo Piccionello A. Pace A. Buscemi S. Vivona N. Giorgi G. Tetrahedron Lett.  2009,  50:  1472 
    Suche in Google Scholar
  • 4f Palumbo Piccionello A. Pace A. Pierro P. Pibiri I. Buscemi S. Vivona N. Tetrahedron  2009,  65:  119 
    Suche in Google Scholar
  • 4g Palumbo Piccionello A. Guarcello A. Buscemi S. Vivona N. Pace A. J. Org. Chem.  2010,  75:  8724 
    Suche in Google Scholar
  • 5a Katritzky AR. Shestopalov AA. Suzuki K. ARKIVOC  2005,  (vii):  36 
    Suche in Google Scholar
  • 5b Nagahara K. Takagi K. Ueda T. Chem. Pharm. Bull.  1975,  23:  3178 
    Suche in Google Scholar
  • 6 Srivastava RM. Rosa MF. Carvalho CEM. Portugal SGM. Brinn IM. Pereira MC. Antunes OAC. Heterocycles  2000,  53:  191 
    Suche in Google Scholar