Skip to main content
SpringerLink
Log in

Crystal Structure of 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one and the Synthesis, Spectral and Thermal Investigation of its Transition Metal Complexes

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

A new 1,2-dihydroquinazolin-4(3H)-one ligand, 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one (Hmpbaq), formed by the condensation of 2-aminobenzoylhydrazide with 2-hydroxy-3-methoxybenzaldehyde and its copper(II), nickel(II), cobalt(II), manganese(II), zinc(II) and cadmium(II) complexes, have been synthesized. Their structures have been elucidated on the basis of elemental analyses, conductance measurements, magnetic moments, spectral (i.r., 1H-n.m.r., u.v.–vis., e.p.r. and FAB-mass) and thermal studies. The formation of 1,2-dihydroquinazolin-4(3H)-one rather than hydrazone in the reaction of 2-aminobenzoylhydrazide with 2-hydroxy-3-methoxybenzaldehyde is confirmed by the 1H-n.m.r. spectra and single crystal X-ray diffraction studies. The tridentate behavior of the ligand was proposed on the basis of spectral studies. X-band e.p.r. spectra of the copper(II) and manganese(II) complexes in the polycrystalline state at room temperature and liquid nitrogen temperature were recorded and their salient features are reported. Thermal stabilities of the manganese(II) and zinc(II) complexes have been studied.

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.

Similar content being viewed by others

References

  1. A.H. Amin D.R. Mehta S.S. Samarth (1970) Prog. Drug Res. 14 218

    Google Scholar 

  2. W.L.F. Armarego, in Fused Pyrimidines, Part I, Quinazolines. D.J. Brown (Ed.) Interscience, New York, 1967.

  3. W.L.F. Armarego (1979) Adv. Heterocycle Chem. 24 1 Occurrence Handle1:CAS:528:DyaL3cXns1ehtQ%3D%3D Occurrence Handle10.1016/S0065-2725(08)60507-3

    Article  CAS  Google Scholar 

  4. K.E. Nielson E.B. Pedersen (1980) Acta Chem. Scand. B34 637 Occurrence Handle10.3891/acta.chem.scand.34b-0637

    Article  Google Scholar 

  5. P.K. Seth S.C. Parmar (1965) Can. J. Physiol. Pharmacol. 43 1019 Occurrence Handle1:CAS:528:DyaF28Xit1Wgug%3D%3D

    CAS  Google Scholar 

  6. J.C. Gupta S.T. Husain A.P. Bhaduri N.M. Khanna S.K. Mukherjee (1969) Nature 223 524 Occurrence Handle1:CAS:528:DyaF1MXksl2mtLo%3D

    CAS  Google Scholar 

  7. G.B. Jackman V. Petrov O. Stephenson (1960) J. Pharm. Pharmacol. 12 529 Occurrence Handle1:CAS:528:DyaF3MXhtlCnsQ%3D%3D

    CAS  Google Scholar 

  8. A. Mannschereck H. Koller G. Shihler M.A. Davies J. Traber (1984) Eur. J. Med. Chem. 19 381

    Google Scholar 

  9. K.B. Gudasi R.S. Vadavi R.V. Shenoy M.S. Patil S.A. Patil M. Nethaji (2005) Transition Met. Chem. 30 661 Occurrence Handle1:CAS:528:DC%2BD2MXpslClt7Y%3D Occurrence Handle10.1007/s11243-005-4829-1

    Article  CAS  Google Scholar 

  10. K.B. Gudasi R.S. Vadavi R.V. Shenoy S.A. Patil M. Nethaji (2006) Transition Met. Chem 31 374 Occurrence Handle1:CAS:528:DC%2BD28XjtFOrurg%3D Occurrence Handle10.1007/s11243-006-0007-3

    Article  CAS  Google Scholar 

  11. S. Ghosh A. Maiti (1987) Proc. Indian Acad. Sci. (Chem. Sci.) 98 185 Occurrence Handle1:CAS:528:DyaL2sXlvV2ntr8%3D

    CAS  Google Scholar 

  12. G.M. Sheldrick (2001) SADABS, Version 2. Multi-Scan Absorption Correction Program University Gottingen Gottingen, Germany

    Google Scholar 

  13. G.M. Sheldrick (1997) SHELX-97, Program for crystal structure solution and refinement University of Gottingen Gottingen, Germany

    Google Scholar 

  14. W.I. Geary (1971) Coord. Chem. Rev. 7 81 Occurrence Handle1:CAS:528:DyaE3MXlsVCgsrg%3D Occurrence Handle10.1016/S0010-8545(00)80009-0

    Article  CAS  Google Scholar 

  15. P.A. Kumar (1998) Indian J. Chem. 37A 460 Occurrence Handle1:CAS:528:DyaK1cXktlCjurs%3D

    CAS  Google Scholar 

  16. B. Prabhakar P. Lingaiah (1991) Indian J. Chem. 30A 904 Occurrence Handle1:CAS:528:DyaK3MXmvFemtrg%3D

    CAS  Google Scholar 

  17. R. Sahni R.S. Agarwal S.S.S. Kushwaha (1982) J. Indian Chem. Soc. 7 853

    Google Scholar 

  18. C.P. Prabhakaran C.C. Patel (1972) J. Inorg. Nucl. Chem. 34 3485 Occurrence Handle1:CAS:528:DyaE38XlsF2lsr0%3D Occurrence Handle10.1016/0022-1902(72)80245-8

    Article  CAS  Google Scholar 

  19. N.V. Thakkar S.Z. Bootwala (1995) Indian J. Chem. 34A 370 Occurrence Handle1:CAS:528:DyaK2MXlt1Ghu7Y%3D

    CAS  Google Scholar 

  20. B. Prabhakar K. Laxma Reddy P. Lingaiah (1988) Indian J. Chem. 27A 217 Occurrence Handle1:CAS:528:DyaL1cXkvVGjtr8%3D

    CAS  Google Scholar 

  21. T.M. Dunn (1960) The Visible and Ultraviolet Spectra of Complex Compounds in Modern Coordination Chemistry Interscience New York

    Google Scholar 

  22. C.H. Krishna C.M. Mahapatra K.C. Dush (1977) J. Inorg. Nucl. Chem. 39 1253 Occurrence Handle10.1016/0022-1902(77)80363-1

    Article  Google Scholar 

  23. V.K. Revenkar V.H. Arali V.B. Mahale (1990) Indian J. Chem. 29A 889

    Google Scholar 

  24. C. Sulekh G. Karuna (2002) Transition Met. Chem. 27 196 Occurrence Handle10.1023/A:1013935602736

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Dharwad, 580 003, India

    Kalagouda B. Gudasi, Siddappa A. Patil, Ramesh S. Vadavi & Rashmi V. Shenoy

  2. Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, 560 012, India

    Munirathinam Nethaji

Authors
  1. Kalagouda B. Gudasi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Siddappa A. Patil
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ramesh S. Vadavi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rashmi V. Shenoy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Munirathinam Nethaji
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kalagouda B. Gudasi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gudasi, K.B., Patil, S.A., Vadavi, R.S. et al. Crystal Structure of 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one and the Synthesis, Spectral and Thermal Investigation of its Transition Metal Complexes. Transition Met Chem 31, 586–592 (2006). https://doi.org/10.1007/s11243-006-0034-0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-006-0034-0

Keywords

Search

Navigation