Download PDF
Synthesis 2010(23): 4107-4118  
DOI: 10.1055/s-0030-1258273
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Practical Synthesis of 5-Aroyl-1-aryltetrazoles Using an Ugi-Like 4-Component Reaction Followed by a Biomimetic Transamination

Mariateresa Giustinianoa, Tracey Piralib, Alberto Massarottib, Beatrice Bilettab, Ettore Novellinoa, Pietro Campigliac, Giovanni Sorbab, Gian Cesare Tron*b
a Dipartimento di Chimica Farmaceutica e Tossicologica, Università di Napoli ‘Federico II’, Via D. Montesano 49, 80131 Napoli, Italy
b Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università degli Studi del Piemonte Orientale ‘A. Avogadro’, Via Bovio 6, 28100 Novara, Italy
Fax: +39(0321)375821; e-Mail: tron@pharm.unipmn.it;
c Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy
Further Information

Publication History

Received 15 June 2010
Publication Date:
28 September 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

Multicomponent reactions (MCRs), followed by subsequent transformations, are fascinating tools for the rapid and effective synthesis of molecular scaffolds with potential pharmacological relevance. We became interested in the preparation of novel 5-aroyl-1-aryltetrazoles as (1) they still represent challenging structures not easily accessible through the methods described in literature, and (2) the α-ketotetrazolic framework may be considered as a potential bioisostere of the enonic linker of chalcones. In the present work, a novel, simple, effective and general synthesis for this class of compounds is described.

Key words

5-aroyl-1-aryltetrazoles - multicomponent reactions - isocyanides - Ugi reaction - chalcones

    References

  • 1 Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. and references cited therein
    Google Scholar
  • 2 Bienaymé H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  29:  123 
    Google Scholar
  • 3 Wender PA. Miller BL. Nature  2009,  460:  197 
    CrossrefGoogle Scholar
  • 4a Marcaccini S. Torroba T. In Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005.  p.33-69  
    Google Scholar
  • 4b Akritopulou-Zanze I. Djuric SW. Heterocycles  2007,  73:  125 
    Google Scholar
  • 4c Hulme C. Nixey T. Curr. Opin. Drug Discovery Dev.  2003,  6:  921 
    Google Scholar
  • 5 Wang W. Herdtweck E. Dömling A. Chem. Commun.  2010,  46:  770 
    CrossrefGoogle Scholar
  • 6 Paulvannan K. Tetrahedron Lett.  1999,  40:  1851 
    CrossrefGoogle Scholar
  • 7 Banfi L. Riva R. Basso A. Synlett  2010,  23 ; and references cited therein
    Article in Thieme ConnectGoogle Scholar
  • 8 Bossio R. Marcaccini S. Pepino R. Torroba T. Heterocycles  1999,  50:  463 
    CrossrefGoogle Scholar
  • 9 Pirali T. Callipari G. Ercolano E. Genazzani AA. Giovenzana GB. Tron GC. Org. Lett.  2008,  10:  4199 
    CrossrefGoogle Scholar
  • 10a Beck B. Larbig G. Mejat B. Magnin-Lachaux M. Picard A. Herdtweck E. Dömling A. Org. Lett.  2003,  5:  1047 
    Google Scholar
  • 10b Oikawa M. Naito S. Sasaki M. Heterocycles  2007,  73:  377 
    Google Scholar
  • 11 Rivera DG. Wessjohann L. J. Am. Chem. Soc.  2009,  131:  3721 
    CrossrefGoogle Scholar
  • 12 Portlock DE. Ostaszewski R. Naskar D. West L. Tetrahedron Lett.  2002,  44:  603 
    Google Scholar
  • 13 In order to quantify the similarity between the chalcone and the proposed structures, a flexible superimposition was performed with Vega ZZ: Pedretti A. Villa L. Vistoli G. J. Mol. Graph. Model  2002,  21:  47 ; the RMSD values of tetrazole was 1.164 Å
    CrossrefGoogle Scholar
  • 14 Ducky S. Anti-Cancer Agents Med. Chem.  2009,  3:  336 
    Google Scholar
  • 15 Moderhack D. J. Heterocycl. Chem.  1977,  14:  757 
    CrossrefGoogle Scholar
  • 16 Zefirov NS. Chapovskaya NK. Tranch SS. Zh. Org. Khim.  1972,  8:  629 
    Google Scholar
  • 17 Demko ZP. Sharpless KB. Angew. Chem. Int. Ed.  2002,  41:  2113 
    CrossrefGoogle Scholar
  • 18 Banfi L. Riva R. Org. React.  2005,  65:  1 
    Google Scholar
  • 19 Olivieri-Mandala E. Alagna B. Gazz. Chim. Ital.  1910,  40:  441 
    Google Scholar
  • 20a Ugi I. Meyr R. Chem. Ber.  1961,  94:  2229 
    Google Scholar
  • 20b Nixey T. Hulme C. Tetrahedron Lett.  2002,  43:  6833 
    Google Scholar
  • 21 Recently Zhu and co-workers demonstrated that the formation of the α-hydroxy amide derivatives depends on catalyst and cannot be suppressed: Yue T. Wang MX. Wang DX. Zhu J. Angew. Chem. Int. Ed.  2008,  47:  9454 
    CrossrefPubMedGoogle Scholar
  • 22a For the Ugi-like 4CR using HN3, see: Ugi I. Angew. Chem., Int. Ed. Engl.  1962,  1:  8 ; Angew. Chem. 1962, 74, 9
    Google Scholar
  • 22b For the Ugi-like 4CR using TMSN3, see: Nixey T. Kelly M. Hulme C. Tetrahedron Lett.  2000,  41:  8729 
    Google Scholar
  • 23 Buckley TF. Rapoport H. J. Am. Chem. Soc.  1982,  104:  4446 
    CrossrefGoogle Scholar