Download PDF
Synthesis 2004(12): 1996-2000  
DOI: 10.1055/s-2004-829195
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Synthesis of Bihetaryl Compounds

Nagatoshi Nishiwaki*, Keiko Yamashita, Mayumi Azuma, Tomoko Adachi, Mina Tamura, Masahiro Ariga*
Department of Chemistry, Osaka Kyoiku University, Asahigaoka 4-698-1, Kashiwara, Osaka 582-8582, Japan
Fax: +81(729)783398; e-Mail: ariga@cc.osaka-kyoiku.ac.jp;
Further Information

Publication History

Received 13 April 2004
Publication Date:
02 August 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

The ring transformation of nitropyrimidinone 1 with ace­tophenone derivatives 2 affords two kinds of azaheterocyclic compounds, 4-phenylpyrimidines 3 and 3-nitro-6-phenyl-2-pyridones 4. On the basis of the relationship between electronic properties of the substituent and ratios of products, a plausible reaction mechanism is provided. Furthermore, the present reaction could be applied to heterocyclic ketones giving bihetaryl compounds.

Key words

ring transformation - nitropyridone - pyrimidine - bihetaryl compounds

    References

  • Reviews for ring transformations:
  • 1a Gromov SP. Heterocycles  2000,  53:  1607 
    Google Scholar
  • 1b van der Plas HC. Adv. Heterocycl. Chem.   Vol. 74:  Academic Press; London: 1999. 
    Google Scholar
  • 1c Takagi K. Hubet-Habart M. J. Heterocycl. Chem.  1996,  33:  1003 
    Google Scholar
  • 1d Rusinov VL. Chupakhin ON. van der Plas HC. Heterocycles  1995,  40:  441 
    Google Scholar
  • 1e van der Plas HC. Ring Transformations of Heterocycles   Vol. 1:  Academic Press; London: 1973. 
    Google Scholar
  • 1f van der Plas HC. Ring Transformations of Heterocycles   Vol. 2:  Academic Press; London: 1973. 
    Google Scholar
  • 2a Nishiwaki N. Matsushima K. Tamura M. Asaka N. Hori K. Tohda Y. Ariga M. Arkivoc  2002,  x:  34 ; www. arkat-usa.org
    CrossrefGoogle Scholar
  • 2b Tohda Y. Kawahara T. Eiraku M. Tani K. Nishiwaki N. Ariga M. Bull. Chem. Soc. Jpn.  1994,  67:  2176 
    CrossrefGoogle Scholar
  • 3a Nishiwaki N. Nakanishi M. Hida T. Miwa Y. Tamura M. Hori K. Tohda Y. Ariga M. J. Org. Chem.  2001,  66:  7535 
    CrossrefGoogle Scholar
  • 3b Nishiwaki N. Ohtomo H. Tamura M. Hori K. Tohda Y. Ariga M. Heterocycles  2001,  55:  1581 
    CrossrefGoogle Scholar
  • 3c Nishiwaki N. Nogami T. Kawamura T. Asaka N. Tohda Y. Ariga M. J. Org. Chem.  1999,  64:  6476 
    CrossrefGoogle Scholar
  • 4a Nishiwaki N. Matsushima K. Chatani M. Tamura M. Ariga M. Synlett  2004,  703 
    Google Scholar
  • 4b Nishiwaki N. Morimura H. Matsushima K. Tamura M. Ariga M. Heterocycles  2003,  61:  19 
    Google Scholar
  • 5 Nishiwaki N. Tohda Y. Ariga M. Synthesis  1997,  1277 
    Article in Thieme ConnectGoogle Scholar
  • 6 Nishiwaki N. Azuma M. Tamura M. Hori K. Tohda Y. Ariga M. Chem. Commun.  2002,  2170 
    CrossrefGoogle Scholar
  • 7 Nishiwaki N. Adachi T. Matsuo K. Wang H.-P. Matsunaga T. Tohda Y. Ariga M. J. Chem. Soc., Perkin Trans. 1  2000,  27 
    CrossrefGoogle Scholar
  • 8a Konakahara T. Ogawa R. Tamura S. Kakehi A. Sakai N. Heterocycles  2001,  55:  1737 
    CrossrefGoogle Scholar
  • 8b Stadlbauer W. Fiala W. Fischer M. Hojas G. J. Heterocycl. Chem.  2000,  37:  1253 
    CrossrefGoogle Scholar
  • 8c Garg R. Gupta SP. Gao H. Babu MS. Debnath AK. Hansch C. Chem. Rev.  1999,  99:  3525 
    CrossrefGoogle Scholar
  • 8d Olejniczak ET. Hajduk PJ. Marcotte PA. Nettesheim DG. Meadows RP. Edalji R. Holzman TF. Fesik SW. J. Am. Chem. Soc.  1997,  119:  5828 
    CrossrefGoogle Scholar
  • 8e Pomel V. Rovera JC. Godard A. Marsais F. Queguiner G. J. Heterocycl. Chem.  1996,  33:  1995 
    CrossrefGoogle Scholar
  • 8f Landquist JK. In Comprehensive Heterocyclic Chemistry   Vol. 1:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.144-183  
    CrossrefGoogle Scholar
  • 8g Brown DJ. In Comprehensive Heterocyclic Chemistry   Vol. 3:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.142-155  
    CrossrefGoogle Scholar
  • 9 Shusherina NP. Likhomanova TI. Chem. Heterocycl. Compd. (Engl. Transl.)  1974,  1242 ; Khim. Geterotskl. Soedin. 1972, 1374
    Google Scholar
  • 10a Balasubrahmanyam SN. Jeyashri B. Namboothiri INN. Tetrahedron  1994,  50:  8127 
    CrossrefPubMedGoogle Scholar
  • 10b Jones H. Fordice MW. Greenwald RB. Hannah J. Jacobs A. Ruyle WV. Walford GL. Shen TY. J. Med. Chem.  1978,  21:  1100 
    CrossrefPubMedGoogle Scholar
  • 11 Bredereck H. Gompper R. Herlinger H. Chem. Ber.  1958,  91:  2832 
    Google Scholar
  • 12 Lynch BM. Poon L. Can. J. Chem.  1967,  45:  1431 
    Google Scholar
  • 13 Brown DJ. England BT. J. Chem. Soc. C  1971,  425 
    CrossrefGoogle Scholar
  • 14 Bennett GB. Mason RB. Alden LJ. Roach JB. J. Med. Chem.  1978,  21:  623 
    CrossrefGoogle Scholar
  • 15a Beauchamp DA. Loeb SJ. Chem. Commun.  2002,  2484 
    Google Scholar
  • 15b Poson MIJ. Lotoski JA. Johansson KO. Taylor NJ. Hanan GS. Hasenknopf B. Thouvenot R. Loiseau F. Passalaqua R. Campagna S. Eur. J. Inorg. Chem.  2002,  2549 
    Google Scholar
  • 15c Cuccia LA. Ruiz E. Lehn J.-M. Homo J.-C. Schmutz M. Chem.-Eur. J.  2002,  8:  3448 
    Google Scholar
  • 16 Egi M. Liebeskind LS. Org. Lett.  2003,  5:  801 
    CrossrefGoogle Scholar
  • 17 Bauer L. Wright GE. Mikrut BA. Bell CL. J. Heterocycl. Chem.  1965,  2:  447 
    Google Scholar