New Tricyclic Ring Systems of Fused 1,4-Diazepines

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[7.2.1.0^³,8]dodec-7-ene - DMAD

References

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

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) Å^³, 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 SHELXS97^¹4 and refined by the full-matrix least-squares method on F ^² using SHELXL97^¹5 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: [phone]; e-mail: [e-mail], under reference number CCDC 720638