Skip to main content
SpringerLink
Log in

Experimental and theoretical investigation of substituent effects in a two-pathway reaction of tetrahydro-1,5-benzodiazepine-2-thiones with 4-substituted 2-bromoacetophenones

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The interaction of 5-acetyl(or formyl)-3-R1(CH3, H)-4-R2(CH3, Ph, H)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine-2-thiones with 2-bromo-4′-X(CH3, OCH3, Br, H)-acetophenones leads to a mixture of products: 5,6-dihydro-4H-[1,3]thiazolo[3,2-a][1,5]benzodiazepinium salts and S-[2-oxo-2-(4-X-phenyl)ethyl] 3-(1H-benzimidazol-1-yl)propane(or butane-)thioate hydrobromides. The course of the concurrent reactions depends on the presence of substituents of the starting thiones and on the nature of the 4-substituent of the bromoacetophenones. Semiempirical Austin method 1 (AM1) and density functional theory (DFT) B3LYP computational studies for the interpretation of two concurrent reaction pathways are presented.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. Di Braccio M, Grossi G, Roma G, Vargiu L, Mura M, Marongiu ME (2001) Eur J Med Chem 36:935

    Article  CAS  Google Scholar 

  2. Janciene R, Vektariene A, Stumbreviciute Z, Kosychova L, Klimavicius A, Puodziunaite BD (2004) Heteroat Chem 15:363

    Article  CAS  Google Scholar 

  3. Janciene R, Stumbreviciute Z, Podeniene D, Puodziunaite BD, Black S, Husbands SM (2006) J Heterocycl Chem 43:979

    Article  CAS  Google Scholar 

  4. Janciene R, Stumbreviciute Z, Vektariene A, Kosychova L, Sirutkaitis R, Palaima A, Staniulyte Z, Puodziunaite BD (2008) Heteroat Chem 19:72

    Article  CAS  Google Scholar 

  5. Janciene R, Kosychova L, Bukelskiene V, Domkus V, Stumbreviciute Z, Ragaleviciene V, Puodziunaite B (2002) Arzneim Forsch 52:475

    CAS  Google Scholar 

  6. For reviews see: Krapcho J, Turk CF (1967) US Patent 3321468; (1968) Chem Abstr 68:21970

  7. Puodzhyunaite BA, Yanchene RA, Stumbryavichyute ZA (1988) Chem Heterocycl Compd 24:786

    Article  Google Scholar 

  8. Okujama T, Kunugiza KT (1974) Bull Chem Soc Jpn 47:1267

    Article  Google Scholar 

  9. Jursic BS (1998) J Mol Struct (Theochem) 427:165

    Article  CAS  Google Scholar 

  10. Jursic BS (1996) Can J Chem 74:114

    Article  CAS  Google Scholar 

  11. Nathaniel R, Mineva T, Nikolova R, Bojilova A (2006) Int J Quantum Chem 106:1357

    Article  CAS  Google Scholar 

  12. Jursic BS, Zdravskovski Z (1995) Int J Quantum Chem 54:161

    Article  CAS  Google Scholar 

  13. Ehresmann B, Martin B, Horn AHC, Clark T (2003) J Mol Model 9:342

    Article  CAS  Google Scholar 

  14. Vektariene A, Vektaris G, Svoboda J (2009) Arkivoc vii:311

    Google Scholar 

  15. Fayet G, Rotureau P, Joubert L, Adamo C (2010) J Mol Model 16:805

    Article  CAS  Google Scholar 

  16. Khandogin J, York DM (2004) Proteins: Struct, Funct, Bioinf 56:724

    Article  CAS  Google Scholar 

  17. Chirlian LE, Francl MM (1987) J Comput Chem 8:894

    Article  CAS  Google Scholar 

  18. Spartan’06, Wavefunction Inc, Irvine, CA. In: Shao Y, Molnar LF, Jung Y, Kussmann J, Ochsenfeld C, Brown ST, Gilbert ATB, Slipchenko LV, Levchenko SV, O’Neill DP, DiStasio Jr RA, Lochan RC, Wang T, Beran GJO, Besley NA, Herbert JM, Lin CY, Van Voorhis T, Chien SH, Sodt A, Steele RP, Rassolov VA, Maslen PE, Korambath PP, Adamson RD, Austin B, Baker J, Byrd EFC, Dachsel H, Doerksen RJ, Dreuw A, Dunietz BD, Dutoi AD, Furlani TR, Gwaltney SR, Heyden A, Hirata S, Hsu C-P, Kedziora G, Khalliulin RZ, Klunzinger P, Lee AM, Lee MS, Liang WZ, Lotan I, Nair N, Peters B, Proynov EI, Pieniazek PA, Rhee YM, Ritchie J, Rosta E, Sherrill CD, Simmonett AC, Subotnik JE, Woodcock III HL, Zhang W, Bell AT, Chakraborty AK, Chipman DM, Keil FJ, Warshel A, Hehre WJ, Schaefer HF, Kong J, Krylov AI, Gill PMW, Head-Gordon M (2006) Phys Chem Chem Phys 8:3172

  19. Parr RG, Yang W (1989) Functional Theory of Atoms and Molecules. Oxford University Press, New York

    Google Scholar 

  20. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordon MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA (1993) J Comput Chem 14:1347

    Article  CAS  Google Scholar 

  21. Parr RG, Yang W (1984) J Am Chem Soc 106:4049

    Article  CAS  Google Scholar 

  22. Ayres PW, Parr RG (2000) J Am Chem Soc 122:2010

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Biochemistry, Vilnius University, Vilnius, Lithuania

    Regina Janciene, Zita Stumbreviciute & Benedikta Puodziunaite

  2. Institute of Theoretical Physics and Astronomy, Vilnius University, Vilnius, Lithuania

    Ausra Vektariene

Authors
  1. Regina Janciene
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ausra Vektariene
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zita Stumbreviciute
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Benedikta Puodziunaite
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Regina Janciene.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Janciene, R., Vektariene, A., Stumbreviciute, Z. et al. Experimental and theoretical investigation of substituent effects in a two-pathway reaction of tetrahydro-1,5-benzodiazepine-2-thiones with 4-substituted 2-bromoacetophenones. Monatsh Chem 142, 609–618 (2011). https://doi.org/10.1007/s00706-011-0496-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0496-4

Keywords

Search

Navigation