Download PDF
Synthesis 2011(5): 783-793  
DOI: 10.1055/s-0030-1258421
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diverse Directions of Heterocyclizations Involving Derivatives of 5-Aminopyrazoles and N-Arylmaleimides

Roman V. Rudenkoa, Sergey A. Komykhov*a, Sergey M. Desenkoa,b, Vladimir I. Musatova, Oleg V. Shishkina, Irina S. Konovalovaa, Elena V. Vashchenkoa, Valentin A. Chebanov*a
a State Scientific Institution ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61001 Kharkiv, Ukraine
Fax: +38(57)3410273; e-Mail: komykhov@isc.kharkov.com; e-Mail: chebanov@isc.kharkov.com;
b Karazin Kharkiv National University, Svobody sq., 4, 61077 Kharkiv, Ukraine
Further Information

Publication History

Received 5 November 2010
Publication Date:
03 February 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Heterocyclization reactions between derivatives of 5-aminopyrazoles and N-arylmaleimides were studied and it was established that several directions are possible. Cyclizations involving 1,3-unsubstituted 5-aminopyrazoles yielded mixtures of two regioisomeric compounds, pyrazolo[1,5-a]pyrimidine-7-carboxamides and pyrazolo[3,4-b]pyridine-4-carboxamides. Reactions of 4-substituted 5-aminopyrazoles in boiling acetic acid or N,N-dimethylformamide in most cases gave pyrazolo[1,5-a]pyrimidine-7-carboxamides as the sole product. The treatment of 1-substituted 5-aminopyrazoles with maleimides possesses high selectivity only in N,N-dimethylformamide yielding pyrazolopyridines while in acetic acid the formation mixtures with pyrrolopyrazolones is observed. The key intermediates of the reaction studied were isolated and discussed.

Key words

heterocycle - N-arylmaleimide - 5-aminopyrazole - pyrazolopyridine - pyrazolopyrimidine

    References

  • See, for example:
  • 1a Alajarin R. Avarez-Buila J. Vaquero JJ. Sunkel C. Fau J. Statkov P. Sanz J. Tetrahedron: Asymmetry  1993,  4:  617 
    Google Scholar
  • 1b Bossert F. Vater W. Med. Res. Rev.  1989,  9:  291 
    Google Scholar
  • 1c Trigle DJ. Langs DA. Janis RA. Med. Res. Rev.  1989,  9:  123 
    Google Scholar
  • 1d Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; WO  8,504,172.  ; Chem. Abstr. 1986, 104, 207298
    Google Scholar
  • 1e Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; JP  61,227,584.  ; Chem. Abstr. 1988, 109, 120988
    Google Scholar
  • 1f Tsuda Y, Mishina T, Obata M, Araki K, Inui J, and Nakamura T. inventors; EP  0,217,142.  ; Chem. Abstr. 1987, 106, 213976
    Google Scholar
  • 1g Atwal KS, Vaccaro W, Lloyd J, Finlay H, Yan L, and Bhandaru RS. inventors; WO  0,140,231.  ; Chem. Abstr. 2003, 135, 19660
    Google Scholar
  • 1h Atwal KS. Moreland S. Bioorg. Med. Chem. Lett.  1991,  1:  291 
    Google Scholar
  • 1i Kappe CO. Eur. J. Med. Chem.  2000,  35:  1043 
    Google Scholar
  • 2a Chebanov VA. Gura KA. Desenko SM. Top. Heterocycl. Chem.  2010,  23:  41 
    Google Scholar
  • 2b Chebanov VA. Desenko SM. Gurley TW. Azaheterocycles Based on α,β-Unsaturated Carbonyls   Springer; Heidelberg: 2008. 
    Google Scholar
  • 2c Chebanov VA. Desenko SM. Curr. Org. Chem.  2006,  10:  297 
    Google Scholar
  • 3a Chebanov VA. Saraev VE. Desenko SM. Chernenko VN. Shishkina SV. Shishkin OV. Kobzar KM. Kappe CO. Org. Lett.  2007,  9:  1691 
    Google Scholar
  • 3b Chebanov VA. Saraev VE. Desenko SM. Chernenko VN. Knyazeva IV. Groth U. Glasnov TN. Kappe CO. J. Org. Chem.  2008,  73:  5110 
    Google Scholar
  • 3c Muravyova EA. Shishkina SV. Musatov VI. Shishkin OV. Desenko SM. Chebanov VA. Synthesis  2009,  1375 
    Google Scholar
  • 3d Chebanov VA. Sakhno YaI. Desenko SM. Chernenko VN. Musatov VI. Shishkina SV. Shishkin OV. Kappe CO. Tetrahedron  2007,  63:  1229 
    Google Scholar
  • 3e Sakhno YaI. Desenko SM. Shishkina SV. Shishkin OV. Sysoyev DO. Groth U. Kappe CO. Chebanov VA. Tetrahedron  2008,  64:  11041 
    Google Scholar
  • 3f Sakhno YaI. Shishkina SV. Shishkin OV. Musatov VI. Vashchenko EV. Desenko SM. Chebanov VA. Mol. Diversity  2010,  14:  523 
    Google Scholar
  • 4a Marrian DH. J. Chem. Soc.  1949,  1797 
    Google Scholar
  • 4b Augustin M. Rudoft D.-W. Pasche R. Z. Chem.  1974,  14:  434 
    Google Scholar
  • 4c Tetsuro S. Yuki M. Tetsuo I. Teruo S. Kenichi S. Heterocycles  2007,  71:  1053 
    Google Scholar
  • 4d Havrylyuk D. Zimenkovsky B. Lesyk R. Phosphorus, Sulfur Silicon Relat. Elem.  2009,  184:  638 
    Google Scholar
  • 4e Rudenko RV. Komykhov SA. Desenko SM. Chem. Heterocycl. Compd. (Engl. Transl.)  2009,  45:  1017 
    Google Scholar
  • 5a Augustin M. Mueller W. J. Prakt. Chem.  1985,  327:  789 
    Google Scholar
  • 5b Ito I. Oda N. Kato T. Chem. Pharm. Bull.  1976,  24:  1189 
    Google Scholar
  • 5c Abelman MM. Fisher KJ. Doerffler E. Edwards PJ. Tetrahedron Lett.  2003,  44:  1823 
    Google Scholar
  • 5d Lesyk R. Vladzimirska O. Holota S. Zaprutko L. Gzella A. Eur. J. Med. Chem.  2007,  42:  641 
    Google Scholar
  • 5e Shah KR. Blanton CD. J. Org. Chem.  1982,  47:  502 
    Google Scholar
  • 6 Rudenko RV. Komykhov SA. Musatov VI. Konovalova IS. Shishkin OS. Desenko SM. J. Heterocycl. Chem.  2011,  in press
    Google Scholar
  • 7a Cobo J. Sánchez A. Nogueras M. Tetrahedron  1998,  54:  5753 
    Google Scholar
  • 7b Velchinskaya E. Petsushak B. Rogal A. Chem. Heterocycl. Compd. (Engl. Transl.)  2007,  43:  695 
    Google Scholar
  • 7c Vel’chinskaya E. Kuzmenko I. Kulik L. Pharm. Chem. J.  1999,  33:  155 
    Google Scholar
  • 8a Nam NL. Grandberg II. Sorokin VI. Khim. Geterotsikl. Soedin.  2000,  342 ; Chem. Heterocycl. Compd. (Engl. Transl.); 2000, 36: 281
    Google Scholar
  • 8b Desenko SM. Orlov VD. Azaheterocycles Based on Aromatic Unsaturated Ketones   Folio; Kharkov: 1998. 
    Google Scholar
  • 9 Zefirov NS. Palyulin VA. Dashevskaya EE. J. Phys. Org. Chem.  1990,  3:  147 
    CrossrefGoogle Scholar
  • 10 Sheldrick GM. Acta Crystallogr., Sect. A  2008,  64:  112 
    CrossrefPubMedGoogle Scholar
11

The final atomic coordinates and crystallographic data for molecule 7l have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk] and is available on request quoting the deposition number CCDC 792559.