Download PDF
Synthesis 2010(8): 1285-1290  
DOI: 10.1055/s-0029-1218700
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of Azaspirodienones by Microwave-Assisted Radical Spirocyclization of Xanthate-Containing Ugi Adducts

Rocío Gámez-Montaño*a, Tannya Ibarra-Riveraa, Laurent El Kaïmb, Luis D. Mirandac
a Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, 36050 Guanajuato, Gto., Mexico
Fax: +52(473)73200068168; e-Mail: rociogm@quijote.ugto.mx;
b Laboratoire Chimie et Procédés, DCSO, UMR 7652, and Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, 75015 Paris, France
c Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, 04510 México, D. F., Mexico
Further Information

Publication History

Received 22 August 2009
Publication Date:
12 March 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The sequential use of an Ugi reaction and radical spirocyclization under microwave irradiation conditions is described. The process provides rapid access to spirodienone lactams.

Key words

Ugi reaction - cyclizations - spiro compounds - lactams - microwave reactions

    References

  • 1 El Kaïm L. Grimaud L. Miranda LD. Vieu E. Tetrahedron Lett.  2006,  47:  8259 
    CrossrefGoogle Scholar
  • 2a Marcaccini S. Torroba T. Org. Prep. Proced. Int.  1993,  25:  141 
    Google Scholar
  • 2b Ugi I. Steinbrückner C. Angew. Chem.  1960,  72:  267 
    Google Scholar
  • 2c Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 2d Zhu J. Eur. J. Org. Chem.  2003,  1133 
    Google Scholar
  • 2e Hulme C. Nixey T. Curr. Opin. Drug Discovery Devel.  2003,  6:  921 
    Google Scholar
  • 3 Renaud P. Sibi M. Radicals in Organic Synthesis   Vols. 1 and 2:  Wiley-VCH; Weinheim: 2001. 
    Google Scholar
  • 4a Quiclet-Sire B. Zard SZ. Chem. Eur. J.  2006,  12:  6002 
    Google Scholar
  • 4b Quiclet-Sire B. Zard SZ. Top. Curr. Chem.  2006,  264:  201 
    Google Scholar
  • 5 Ibarra-Rivera TR. Gámez-Montaño R. Miranda LD. Chem. Commun.  2007,  3485 
    CrossrefGoogle Scholar
  • 6a Kita Y. Takada T. Gyoten M. Tohma H. Zenk MH. Eichhorn J. J. Org. Chem.  1996,  61:  5857 
    Google Scholar
  • 6b Perry NB. Blunt JW. McCombs JD. Munro MH. J. Org. Chem.  1986,  51:  5476 
    Google Scholar
  • 6c Blunt JW. Calder VL. Fenwick GD. Lake RJ. McCombs JD. Munro MH. Perry NB. J. Nat. Prod.  1987,  59:  290 
    Google Scholar
  • 6d Perry NB. Blunt JW. Munro MH. Higa T. Sakai R. J. Org. Chem.  1988,  53:  4127 
    Google Scholar
  • 6e Perry NB. Blunt JW. Munro MH. Tetrahedron  1988,  44:  1727 
    Google Scholar
  • 6f Martin SF. In Alkaloids   Vol. 30:  Brossi A. Academic Press; New York: 1987.  p.251 
    Google Scholar
  • 6g Tanaka A. Kawai T. Takabatake T. Oka N. Okamoto H. Bersohn M. Tetrahedron Lett.  2006,  47:  6733 
    Google Scholar
  • 6h Badger AM. Schwartz DA. Picker DH. Dorman JW. Bradley FC. Cheeseman EN. DiMartino MJ. Hanna N. Mirabelli CK. J. Med. Chem.  1990,  33:  2963 
    Google Scholar
  • 6i Shigehisa H. Takayama J. Honda T. Tetrahedron Lett.  2006,  47:  7301 
    Google Scholar
  • 7 Santra S. Andreana PR. Org. Lett.  2007,  9:  5035 
    CrossrefPubMedGoogle Scholar
  • For reviews, see:
  • 8a Sinnwell S. Ritter H. Aust. J. Chem.  2007,  60:  729 
    Google Scholar
  • 8b Wiesbrock F. Hoogenboom R. Schubert US. Macromol. Rapid Commun.  2004,  25:  1739 
    Google Scholar
  • See also:
  • 8c Pawluczyk JM. McClain RT. Denicola CM. James J. Rudd DJ. Lindsley CW. Tetrahedron Lett.  2007,  48:  1497 
    Google Scholar
  • 9a Portela-Cubillo F. Scott JS. Walton JC. Chem. Commun.  2007,  4041 
    Google Scholar
  • 9b Bull JA. Hutchings MG. Quayle P. Angew. Chem. Int. Ed.  2007,  46:  1869 
    Google Scholar
  • 9c Jessop CM. Parsons AF. Routledge A. Irvine DJ. Eur. J. Org. Chem.  2006,  1547 
    Google Scholar
  • 9d Zhang W. Top. Curr. Chem.  2006,  266:  145 
    Google Scholar
  • 9e Schulte B. Studer A. Synthesis  2006,  2129 
    Google Scholar
  • 9f Wetter C. Studer A. Chem. Commun.  2004,  174 
    Google Scholar
10

Microwave reactions were conducted using a CEM Discover Synthesis™ Unit (CEM Corp., Matthews, NC); see: http://www.cem.com/page176.html.