Synthesis 2010(7): 1107-1112  
DOI: 10.1055/s-0029-1219235
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Chemical Reactivity of New Azaenamines Incorporated the 4,5,6,7-Tetrahydrobenzo[b]thiophene Moiety: 3+3 Atom Combination

Ismail Abdelshafy Abdelhamid*a,b, Elham Sayed Darwisha, Miead Adel Nasraa, Fathy Mohamed Abdel-Gallila, Daisy Hanna Fleitac
a Chemistry Department, Faculty of Science, Cairo University, Giza, A. R. Egypt
Fax: +20(2)35727556; e-Mail: ismail_shafy@yahoo.com;
b Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany
c Chemistry Department, American University in Cairo, Egypt
Further Information

Publication History

Received 17 November 2009
Publication Date:
20 January 2010 (eFirst)

Abstract

Novel azaenamines incorporating a tetrahydrothiophene moiety were prepared. Michael addition of an azaenamine with α,β-unsaturated nitriles took place to give [1]benzothieno[3′,2′:5,6]pyrimido[1,2-b]pyridazine (thia-triaza-benzo[a]fluorene) derivatives. The condensation with malononitrile resulted in the formation of a [1]benzothieno[3′,2′:5,6]pyrimido[1,2-b]pyridazine-4-carbonitrile. The azaenamine also reacted with aldehydes and piperidine to give Mannich products.

    References

  • 1 LaPorte MG. Lessen TA. Leister L. Cebzanov D. Amparo E. Faust C. Ortlip D. Bailey TR. Nitz TJ. Chunduru SK. Young DC. Burns CJ. Bioorg. Med. Chem. Lett.  2006,  16:  100 
  • 2 Amidshiro SN. Kobayashi E. Gomi K. Satio H. J. Med. Chem.  1999,  42:  669 
  • 3 Fujii K, Tsutsminichi K, Yamanaka Y, and Nakamura K. inventors; JP  11,116,555.  1999; Chem. Abstr. 1999, 130: 325151w
  • 4 Reinhard R, Rack M, Walter H, Zagar C, Otten M, Munster P, Westphalen K.-O, Menges M, Menke O, Schafer P, and Hamprecht G. inventors; WO  9,914,201.  1999; Chem. Abstr. 1999, 130, 223288d
  • 5 Cheung M, Glennon CK, Lackey EK, and Peel PM. inventors; WO  9,921,859.  1999; Chem. Abstr. 1999, 130, 325139y
  • 6 Baraldi GP. inventors; WO  9,921,617.  1999; Chem. Abstr. 1999, 130, 296427h
  • 7 Wolfbeis OS. Monatsh. Chem.  1981,  112:  875 
  • 8 Abdelhamid IA. Mohamed MH. Abdelmoniem AM. Ghozlan SAS. Tetrahedron  2009,  65:  10069 
  • 9 Ghozlan SAS. Mohamed MH. Abdelmoniem AM. Abdelhamid IA. ARKIVOC  2009,  (x):  302 
  • 10 Ghozlan SAS. Abdelhamid IA. Hassaneen HM. Elnagdi MH. J. Heterocycl. Chem.  2007,  44:  105 
  • 11 Abdelhamid IA. Synlett  2009,  625 
  • 12 Ghozlan SAS. Abdelhamid IA. Elnagdi MH. ARKIVOC  2006,  (xiii):  147 
  • 13 Sayed GH. Hamed AA. Meligi GA. Boraie WE. Shafik M. Molecules  2003,  8:  322 
  • 14 Kabalka GW. Zhou L.-L. Wang L. Pagni RM. Tetrahedron  2006,  62:  857 
  • 15 Wu H. Shen Y. Fan L.-Y. Wan Y. Zhang P. Chen C.-F. Wang W.-X. Tetrahedron  2007,  63:  2404 
  • 16 Shi M. Cui S.-C. Liu Y.-H. Tetrahedron  2005,  61:  4965