Skip to main content
SpringerLink
Log in

Diverse Confirmations in the Crystal Structures of 2,3-Dihydro-2,2-dimethylquinazolin-4(1H)-one Derivatives

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstracts

The 3-(propan-2-ylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one and 3-(3-nitrobenzylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one were synthesized and characterized by IR, 1H NMR and HRMS. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C13H17N3O, is monoclinic, space group P2(1)/c, a = 9.056(2), b = 9.439(2), c = 14.872(3) Å, β = 133.121(12)°, Z = 4, V = 1270.9(5) Å3. The latter 2, C17H16N4O3, is also monoclinic, space group P2(1)/c, a = 10.0006(2), b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3. It is very interesting that the pyrimidine ring in the 1 adopts a half-chair confirmation, while adapting a skew-boat one in the structure of 2.

Graphical Abstract

The 3-(propan-2-ylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one and 3-(3-nitrobenzylideneamino)-2,3-dihydro-2,2-dimethylquinazolin-4(1H)-one were synthesized and characterized by IR, 1H NMR and HRMS. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C13H17N3O, is monoclinic, space group P2(1)/c, a = 9.056(2), b = 9.439(2), c = 14.872 (3) Å, β = 133.121(12)°, Z = 4, V = 1270.9 (5) Å3. The latter 2, C17H16N4O3, is also monoclinic, space group P2(1)/c, a = 10.0006(2), b = 12.2298(3), c = 13.3255(3) Å, β = 96.602(2)°, Z = 4, V = 1618.97(6) Å3. It is very interesting that the pyrimidine ring in the 1 adopts a half-chair confirmation, while adapting a skew-boat one in the structure of 2.

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

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Fry DW, Kraker AJ, McMichael A, Ambroso LA, Nelson JM, Leopold WR, Connors RW, Bridges AJ (1994) Science 265:1093

    Article  CAS  Google Scholar 

  2. Laszlo SE, Chang RS, Cheng TB, Faust KA, Greenlee WJ, Kivlighn SD, Lotti VJ, O’Malley SS, Schorn TW, Siegl PK, Tran J, Zingaro GJ (1995) Bioorg Med Chem Lett 5:1359

    Article  Google Scholar 

  3. Johne S (1981) Pharmazie 36:583

    CAS  Google Scholar 

  4. Horton DA, Bourne GT, Smythe ML (2003) Chem Rev 103:893

    Article  CAS  Google Scholar 

  5. Liu JF, Wilson CJ, Ye P, Sprague K, Sargent K, Si Y, Beletsky G, Yohannes D, Ng SC (2006) Bioorg Med Chem Lett 16:686

    Article  CAS  Google Scholar 

  6. Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, Lundell GF, Veber DF, Anderson PS, Chang RSL, Lotti VJ, Cerino DJ, Chen TB, Kling PJ, Kunkel KA, Springer JP, Hirshfieldt J (1988) J Med Chem 31:2235

    Article  CAS  Google Scholar 

  7. Duarte CD, Barreiro EJ, Fraga CAM (2007) Mini-Rev Med Chem 7:1108

    Article  CAS  Google Scholar 

  8. Alagarsamy V, Raja SV, Dhanabal K (2007) Bioorg Med Chem 15:235

    Article  CAS  Google Scholar 

  9. Alagarsamy V, Pathak US (2007) Bioorg Med Chem 15:3457

    Article  CAS  Google Scholar 

  10. Murugan V, Kulkarni M, Anand RM, Kumar EP, Suresh B, Reddy VM (2006) Asian J Chem 18:900

    CAS  Google Scholar 

  11. Godfrey AAA (2005) PCT Int Appl WO 2005012260 A2 10 Feb (2005) Chem Abstr 142:198095

  12. Selvam P, Girija K, Nagarajan G, De Clerco E (2005) Indian J Pharm Sci 67:484

    CAS  Google Scholar 

  13. Alanine A, Gobbi LC, Kolczewski S, Luebbers T, Peters J-U, Steward L (2006) US Pat US 2006293350 A1 28 Dec (2006) Chem Abstr 146:100721

  14. Chaturvedula PV, Chen L, Civiello R, Degnan AP, Dubowchik GM, Han X, Jiang XJ, Macor JE, Poindexter GS, Tora GO, Luo G (2007) US Pat US 2007149503 A1 28 Jun (2007) Chem Abstr 147:118256

  15. Letourneau J, Riviello C, Ho K-K, Chan J-H, Ohlmeyer M, Jokiel P, Neagu I, Morphy JR, Napier SE (2006) PCT Int Appl WO 2006095014 A1 14 Sep (2006) Chem Abstr 145:315012

  16. Sheldrick GM (2008) Acta Cryst A64:112

    CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Natural Science foundation of China (20802061), a project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions and Qing Lan Project (08QLT001, 10QLD008) of Jiangsu Education Committee for financial support.

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Jie Sheng, Mei-Mei Zhang, Lian Lu & Xiang-Shan Wang

  2. The Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Jie Sheng, Mei-Mei Zhang, Lian Lu & Xiang-Shan Wang

Authors
  1. Jie Sheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mei-Mei Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lian Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiang-Shan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xiang-Shan Wang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sheng, J., Zhang, MM., Lu, L. et al. Diverse Confirmations in the Crystal Structures of 2,3-Dihydro-2,2-dimethylquinazolin-4(1H)-one Derivatives. J Chem Crystallogr 42, 701–705 (2012). https://doi.org/10.1007/s10870-012-0303-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-012-0303-z

Keywords

Search

Navigation