Synthesis 2013; 45(8): 1051-1059
DOI: 10.1055/s-0032-1318476
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Transformation of Inactive Nitriles into 5-Substituted 1H-Tetrazoles Using Microwave Irradiation and Their Applications

Hiroki Yoneyama
a   Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan   Fax: +81(72)6901086   eMail: harusawa@gly.oups.ac.jp
,
Yoshihide Usami
a   Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan   Fax: +81(72)6901086   eMail: harusawa@gly.oups.ac.jp
,
Seiji Komeda
b   Faculty of Pharmaceutical Sciences, Suzuka University of Medical Science, Suzuka, Mie 513-8670, Japan
,
Shinya Harusawa*
a   Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan   Fax: +81(72)6901086   eMail: harusawa@gly.oups.ac.jp
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 09. Januar 2013

Accepted after revision: 25. Februar 2013

Publikationsdatum:
08. März 2013 (online)


Abstract

Efficient transformations of inactive nitriles into 5-substituted 1H-tetrazoles in DMF in a microwave reactor are described. The present method is applied to the synthesis of tetrazolato-bridged dinuclear platinum(II) complex and tetrazole C1-ribonucleoside phosphoramidite.

Supporting Information

 
  • References


    • For recent reviews on tetrazoles, see:
    • 1a Bhatt U. Five-membered Heterocycles with Four Heteroatoms: Tetrazoles . In Modern Heterocyclic Chemistry . Vol. 3. Alvarez-Builla J, Vaquero JJ, Barluenga J. Wiley-VCH; Weinheim: 2011: 1401
    • 1b Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379
    • 1c Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
    • 1d Butler RN. Tetrazoles . In Comprehensive Heterocyclic Chemistry II . Vol. 4. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 621
  • 2 Finnegan WG, Henry RA, Lofquist R. J. Am. Chem. Soc. 1958; 80: 3908
  • 3 Demko ZP, Sharpless KB. J. Org. Chem. 2001; 66: 7945
    • 4a Alterman M, Hallberg A. J. Org. Chem. 2000; 65: 7984
    • 4b Schmidt B, Meid D, Kieser D. Tetrahedron 2007; 63: 492
    • 4c Myznikov LV, Roh J, Artamonova TV, Hrabalek A, Koldobskii GI. Russ. J. Org. Chem. 2007; 43: 765
    • 4d Shie J.-J, Fang J.-M. J. Org. Chem. 2007; 72: 3141
    • 4e Zhao Z, Leister WH, Robinson RG, Barnett SF, Defeo-Jones D, Jones RE, Hartman GD, Huff JR, Huber HE, Duggan ME, Lindsley CW. Bioorg. Med. Chem. Lett. 2005; 15: 905
    • 4f Marvi O, Alizadeh A, Zarrabi S. Bull. Korean Chem. Soc. 2011; 32: 4001
    • 4g Patil VS, Nandre KP, Borse AU, Bhosale SV. E-J. Chem. 2012; 9: 1145
    • 4h Myznikov LV, Efimova YA, Artamonova TV, Koldobskii GI. Russ. J. Org. Chem. 2011; 47: 728
    • 4i Sakhuja R, Panda SS, Bajaj K. Curr. Org. Chem. 2012; 16: 789
    • 4j Kappe CO, Stadler A, Dallinger D. Microwaves in Organic and Medicinal Chemistry . In Methods and Principles in Medicinal Chemistry . Vol. 52. Mannhold R, Kubinyi H, Folkers G. Wiley-VCH; Weinheim: 2012: 487
    • 5a Bliznets IV, Vasil’ev AA, Shorshnev SV, Stepanov AE, Lukyanov SM. Tetrahedron Lett. 2004; 45: 2571
    • 5b Schulz MJ, Coats SJ, Hlasta DJ. Org. Lett. 2004; 6: 3265
    • 5c Ek F, Manner S, Wistrand L.-G, Frejd T. J. Org. Chem. 2004; 69: 1346
  • 6 Roh J, Artamonova TV, Vávrová K, Koldobskii GI, Hrabálek A. Synthesis 2009; 2175
    • 7a Komeda S, Lin Y.-L, Chikuma M. ChemMedChem 2011; 6: 987
    • 7b Komeda S. Metallomics 2011; 3: 650
    • 8a Harusawa S, Yoneyama H, Fujisue D, Nishiura M, Fujitake M, Usami Y, Zhao Z, McPhee SA, Wilson TJ, Lilley DM. J. Tetrahedron Lett. 2012; 53: 5891
    • 8b Araki L, Harusawa S, Yamaguchi M, Yonezawa S, Taniguchi N, Lilley DM. J, Zhao Z, Kurihara T. Tetrahedron Lett. 2004; 45: 2657
    • 8c Araki L, Harusawa S, Yamaguchi M, Yonezawa S, Taniguchi N, Lilley DM. J, Zhao Z, Kurihara T. Tetrahedron 2005; 61: 11976
    • 8d Araki L, Morita K, Yamaguchi M, Zhao Z, Wilson TJ, Lilley DM. J, Harusawa S. J. Org. Chem. 2009; 74: 2350
    • 8e Araki L, Zhao Z, Lilley DM. J, Harusawa S. Heterocycles 2010; 81: 1861
    • 8f Harusawa S, Fujii K, Nishiura M, Araki L, Usami Y, Zhao Z, Lilley DM. J. Heterocycles 2011; 83: 2041
    • 8g Araki L, Harusawa S. Yakugaku Zasshi 2010; 130: 1707
    • 9a Zhao Z, McLeod A, Harusawa S, Araki L, Yamaguchi M, Kurihara T, Lilley DM. J. J. Am. Chem. Soc. 2005; 127: 5026
    • 9b Wilson TJ, Ouellet J, Zhao Z, Harusawa S, Araki L, Kurihara T, Lilley DM. J. RNA 2006; 12: 980
    • 9c Lilley DM. J. Biol. Chem. 2007; 388: 699
    • 9d Wilson TJ, Nahas M, Araki L, Harusawa S, Ha T, Lilley DM. J. Blood Cell Mol. Dis. 2007; 38: 8
  • 10 The synthesis of C0- and C2-ribonucleoside phosphoramidites and their incorporation into RNA were reported in reference 8a.
    • 11a Fujitake M, Harusawa S, Araki L, Yamaguchi M, Lilley DM. J, Zhao Z, Kurihara T. Tetrahedron 2005; 61: 4689
    • 11b Fujitake M, Harusawa S, Zhao Z, Lilley DM. J, Kurihara T. Bull. Osaka Univ. Pharm. Sci. 2007; 1: 107
    • 11c Harusawa S, Fujitake M, Kurihara T, Zhao Z, Lilley DM. J. Mass Determination of Phosphoramidites . In Current Protocols in Nucleic Acid Chemistry . Beaucage SL, Bergstrom DE, Herdewijn P, Matsuda A. Wiley; New York: 2006. 10.11.1
    • 11d Fujitake M, Harusawa S. Bull. Osaka Univ. Pharm. Sci. 2011; 5: 49
  • 12 Mihina JS, Herbst RM. J. Org. Chem. 1950; 15: 1082
  • 13 Fleming A, Kelleher F, Mahon MF, McGinly J, Prajapati V. Tetrahedron 2005; 61: 7002
  • 14 Popova EA, Pavlyukova YN, Popov EV, Ostrovskill VA, Trifonov RE. Russ. J. Org. Chem. 2009; 45: 890
  • 15 Jin T, Kitahara F, Kamijo S, Yamamoto Y. Tetrahedron Lett. 2008; 49: 2824
  • 16 Aureggi V, Sedelmeier G. Angew. Chem. Int. Ed. 2007; 46: 8440