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Synlett 2008(18): 2895-2896  
DOI: 10.1055/s-2008-1067230
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

1H-Benzotriazoles

Luísa C. C. R. Carvalho*
REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal
e-Mail: luisa_carvalho@dq.fct.unl.pt;
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Publikationsdatum:
15. Oktober 2008 (online)

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Introduction

1H-Benzotriazole (BtH) is a non-volatile, white crystalline powder that melts at 98.5 ˚C. It is insoluble in water, but soluble in aqueous sodium carbonate, and in ethanol. It is intrinsically unreactive, stable under many conditions, cheap, and ready available. Because of its chemical properties, it can be used as a valuable synthetic auxiliary, allowing an enormous variety of reactions. [¹] A benzotriazole group activates the carbon atom to which it is attached in various ways: by acting as a leaving group; by enabling deprotonation; or by acting as an electron donor. An attached benzotriazole group is also an ambient anion-directing group and it can act as a radical or carbanion precursor. [¹]

1H-Benzotriazole is involved in several reactions, including: Bt-mediated N- and C-acylations; [²] imidoylation reactions; [³] thioacylation and sulfonylations; [4] insertion reactions; [5] amido- and amino-alkylations; [6] synthesis of heterocycles; [7] and reactions involving the cleavage of a benzotriazole ring. [8] It can be also used in Wittig rearrangements, VNS (vicarious nucleophilic substitutions), and radical-mediated reactions. [9]

BtH can be prepared according to a simple procedure in which, to a cooled sodium nitrite solution, is added an aqueous o-phenylenediamine and glacial acetic acid solution (Figure  [¹] ). [¹0]

Figure 1

    References

  • 1a Katritzky A. Rogovoy B. Chem. Eur. J.  2003,  9:  4586 
    Google Scholar
  • 1b Katritzky A. Lan X. Yang J. Denisko O. Chem. Rev.  1998,  98:  409 
    Google Scholar
  • 2a Katritzky A. Abdel-Fattah A. Wang M. J. Org. Chem.  2003,  68:  1443 
    Google Scholar
  • 2b Katritzky A. Mohapatra P. Fedoseyenko D. Duncton M. Steel P. J. Org. Chem.  2007,  72:  4268 
    Google Scholar
  • 2c Katritzky A. Le K. Khelashvili L. Mohapatra P. J. Org. Chem.  2006,  71:  9861 
    Google Scholar
  • 3 Katritzky A. Rogovoy B. Cai X. Kirichenko N. Kovalenko K. J. Org. Chem.  2004,  69:  309 
    CrossrefGoogle Scholar
  • 4 Katritzky A. Abdel-Fattah A. Vakulenko A. Tao H. J. Org. Chem.  2005,  70:  9191 
    CrossrefGoogle Scholar
  • 5a Katritzky A. Bobrov S. Khashab N. Kirichenko K. J. Org. Chem.  2004,  69:  4269 
    Google Scholar
  • 5b Katritzky A. Bobrov S. Kirichenko K. Ji Y. J. Org. Chem.  2004,  69:  303 
    Google Scholar
  • 5c Katritzky A. Xie L. Serdyuk L. J. Org. Chem.  1996,  2:  7564 
    Google Scholar
  • 6 Katritzky AR. Manju K. Singh SK. Meher N. Tetrahedron  2005,  61:  2555 
    CrossrefGoogle Scholar
  • 7 Katritzky A. Xu Y. He H. J. Chem. Soc., Perkin Trans. 1  2002,  592 
    CrossrefGoogle Scholar
  • 8 Micó X. Bombarelli R. Subramanian L. Ziegler T. Tetrahedron Lett.  2006,  47:  7845 
    CrossrefGoogle Scholar
  • 10 Chan M, and Hunter W. inventors; US Patent  4299965.  ; Chem. Abstr. 96, 85560n
  • 11 Katritzky A. Cai C. Singh S. J. Org. Chem.  2006,  71:  3375 
    CrossrefGoogle Scholar
  • 12 Katritzky A. Khelashvili L. Le K. Mohapatra P. Steel P. J. Org. Chem.  2007,  72:  5805 
    CrossrefPubMedGoogle Scholar
  • 13 Katritzky A. Le K. Khelashvili L. Mohapatra P. J. Org. Chem.  2006,  71:  9861 
    CrossrefGoogle Scholar
  • 14 Androsov D. Neckers D. J. Org. Chem.  2007,  72:  1148 
    CrossrefGoogle Scholar
  • 15 Deguest G. Bischoff L. Fruit C. Marsais F. Org. Lett.  2007,  9:  1165 
    CrossrefGoogle Scholar
9

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