Download PDF
Synthesis 2010(10): 1654-1658  
DOI: 10.1055/s-0029-1218710
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Tricyclic Ring Systems of Fused 1,4-Diazepines

Barbara Zaleska*a, Marcin Karelusa, Pawe Serdab
a Department of Organic Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Kraków, Poland
Fax: 48(12)6340515; e-Mail: zaleska@chemia.uj.edu.pl;
b Regional Laboratory of Physicochemical Analysis and Structural Research, ul. R. Ingardena 3, 30-060 Kraków, Poland
Further Information

Publication History

Received 16 February 2010
Publication Date:
24 March 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

New heterocyclic systems of pyrimido[1,2-d][1,4]diazepine, [1,4]diazepino[7,1-b]quinazoline, and [1,4]diazepino[1,7-a][1,3]diazepine were obtained in specific reactions of DMAD with zwitterionic compounds.

Key words

pyrimido[1,2-d][1,4]diazepine - [1,4]diazepino[7,1-b]quinazoline - [1,4]diazepino[1,7-a][1,3]diazepine - triazatricy­clo[7.2.1.0³,8]dodec-7-ene - DMAD

    References

  • 1a Lueddens H. Korpi ER. Handbook of Contemporary Neuropharmacology   Vol. 2:  Wiley; New York: 2007.  p.93 
    Google Scholar
  • 1b Bacon ER. Chatterjee S. Williams M. Comprehensive Medicinal Chemistry II   Vol. 6:  Elsevier; Amsterdam: 2006.  p.139 
    Google Scholar
  • 1c Da Settimo F. Taliani S. Trincavelli ML. Montali M. Martini C. Curr. Med. Chem.  2007,  14:  2680 
    Google Scholar
  • 2 Herpin TF. Van Kirk KG. Salvino JM. Yu ST. Labaudiniere RF. J. Comb. Chem.  2000,  2:  513 
    CrossrefPubMedGoogle Scholar
  • 3a Kamal A. Khan MNA. Reddy KS. Ahmed SK. Kumar MS. Juvekar A. Sen S. Zingde S. Bioorg. Med. Chem. Lett.  2007,  17:  5345 
    Google Scholar
  • 3b Antonow D. Cooper N. Howard PW. Thurston DE. J. Comb. Chem.  2007,  9:  437 
    Google Scholar
  • 3c Kamal A. Reddy DR. Reddy PSMM. Bioorg. Med. Chem. Lett.  2007,  17:  803 
    Google Scholar
  • 3d Kamal A. Shankaraiah N. Devaiah V. Reddy KL. Tetrahedron Lett.  2006,  47:  6553 
    Google Scholar
  • 3e Kang G.-D. Howard PW. Thurston DE. Chem. Commun.  2003,  1688 
    Google Scholar
  • 3f Cooper N. Hagan DR. Tiberghien A. Ademefun T. Matthews CS. Howard PW. Thurston DE. Chem. Commun.  2002,  1764 
    Google Scholar
  • 3g Kamal A. Ramu R. Khanna GBR. Saxena AK. Shanmugavel M. Pandita RM. ARKIVOC  2005,  (iii):  83 
    Google Scholar
  • 3h Hurley LH. Boyed FL. Trends Pharmacol. Sci.  1988,  9:  402 
    Google Scholar
  • 3i Zhilina ZV. Ziemba AJ. Trent JO. Reed MW. Gorn V. Zhov Q. Duan W. Hurley L. Ebbinghaus SW. Bioconjugate Chem.  2004,  15:  1182 
    Google Scholar
  • 3j Kumar R. Lown JW. Mini-Rev. Med. Chem.  2003,  3:  323 
    Google Scholar
  • 4 Dervan PB. Science  1986,  232:  464 
    CrossrefGoogle Scholar
  • 5 Ruano JLG. Fajardo C. Fraile A. Martin MR. Soriano JF. ARKIVOC  2010,  (iii):  303 
    Google Scholar
  • 6 Smish L. Wong WC. Kiselyov A. Burdzvic-Wizeman S. Mao Y. Xu Y. Duncton MAJ. Kim K. Piatnitski EL. Doody JF. Wang Y. Rosler RL. Milligan D. Columbus J. Balagtas C. Lee SP. Konovalov A. Hadari YR. Bioorg. Med. Chem. Lett.  2006,  16:  5102 
    CrossrefGoogle Scholar
  • 7 Al-Said NH. Al-Qaisi LS. Tetrahedron Lett.  2006,  47:  693 
    CrossrefGoogle Scholar
  • 8 Hill RA. Annu. Rep. Prog. Chem., Chem. Sect. B  2009,  105:  150 
    Google Scholar
  • 9 Zaleska B. Bazanek T. Socha R. Karelus M. Grochowski J. Serda P. J. Org. Chem.  2002,  67:  4526 
    CrossrefPubMedGoogle Scholar
  • 10 Zaleska B. Karelus M. Synlett  2002,  1831 
    Article in Thieme ConnectGoogle Scholar
  • 11 Zaleska B. Karelus M. Zadora E. Kruszewska H. Synthesis  2005,  2946 
    Article in Thieme ConnectGoogle Scholar
  • 12 Zaleska B. Karelus M. Flasinski M. Serda P. ARKIVOC  2007,  (vi):  64 
    Google Scholar
  • 14 Sheldrick GM. SHELXS97 - Program for Crystal Structure Solution   University of Göttingen; Göttingen: 1997. 
    Google Scholar
  • 15 Sheldrick GM. SHELXL97 - Program for Crystal Structure Refinement   University of Göttingen; Göttingen: 1997. 
    Google Scholar
  • 16 Farrugia LJ. J. Appl. Crystallogr.  1997,  32:  837 
    CrossrefGoogle Scholar
13

Compound 11 with formula C18H19N3O4S crystallises in the triclinic system, space group P1, with unit cell parameters a = 8.8020 (2), b = 10.1138 (2), c = 11.1187 (2) Å, α = 74.932 (1), β = 75.122 (1), γ = 74.018 (1)˚, V = 900.36 (3) ų, Z = 2. A total of 4115 independent reflections [R(int) = 0.0278] were collected on a sample (size 0.3 × 0.2 × 0.15 mm) using KappaCCD diffractometer and MoKα radiation. The structure was solved by direct methods with SHELXS97¹4 and refined by the full-matrix least-squares method on F ² using SHELXL97¹5 program. Final discrepancy indices for I > 2σ(I) were equal R1 = 0.0573, wR2 = 0.1048 and R1 = 0.091, wR2 = 0.1642 for all data. The final difference Fourier map of electron density had the largest peak and hole of 0.61 and -0.305 e˙Å-³, respectively. All calculations and molecular graphics were done using the WinGX package.¹6 The structural data were deposited at the Cambridge Crystallographic Data Centre. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html, or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk, under reference number CCDC 720638