Skip to main content
SpringerLink
Log in

Efficient \(\hbox {Cu(OTf)}_{2}\)-catalyzed synthesis of novel and diverse 2,3-dihydroquinazolin-4(1\(H\))-ones

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

An efficient one-pot synthesis of various 2,3-dihydroquinazolin-\(4(1H)\)-one derivatives was accomplished using \(\hbox {Cu}(\hbox {OTf})_{2}\)-catalyzed multi-component reactions between isatoic anhydride, ketones, and amines. The method has several significant advantages; mild reaction conditions, easy handling, and efficiency of catalyst.

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
Scheme 3

Similar content being viewed by others

References

  1. Mhaske SB, Argade NP (2006) The chemistry of recently isolated naturally occurring quinazolinone alkaloids. Tetrahedron 62:9787–9826. doi:10.1016/j.tet.2006.07.098

    Article  CAS  Google Scholar 

  2. Michael JP (2004) Quinoline, quinazoline and acridone alkaloids. Nat Prod Rep 21:650–668. doi:10.1039/b310691h

    Article  CAS  PubMed  Google Scholar 

  3. Horton DA, Bourne GT, Smythe ML (2003) The combinatorial synthesis of bicyclic privileged structures or privileged substructures. Chem Rev 103:893–930. doi:10.1021/cr020033s

    Article  CAS  PubMed  Google Scholar 

  4. Chinigo GM, Paige M, Grindrod S, Hamel E, Dakshanamurthy S, Chruszcz M, Minor W, Brown ML (2008) Asymmetric synthesis of 2,3-dihydro-2-arylquinazolin-4-ones: methodology and application to a potent fluorescent tubulin inhibitor with anticancer activity. J Med Chem 51:4620–4631. doi:10.1021/jm800271c

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  5. Wang Z, Wang M, Yao X, Li Y, Tan J, Wang L, Qiao W, Geng Y, Liu Y, Wang Q (2012) Design, synthesis and antiviral activity of novel quinazolinones. Eur J Med Chem 53:275–282. doi:10.1016/j.ejmech.2012.04.010

    Article  CAS  PubMed  Google Scholar 

  6. Abbas SE, Awadallah FM, Ibrahin NA, Said EG, Kamel GM (2012) New quinazolinone-pyrimidine hybrids: synthesis, anti-inflammatory, and ulcerogenicity studies. Eur J Med Chem 53:141–149. doi:10.1016/j.ejmech.2012.03.050

    Article  CAS  PubMed  Google Scholar 

  7. Ismail MAH, Barker S, Abouzid KAM, Toubar RA, Todd MH (2006) Design and synthesis of new tetrazolyl- and carboxy-biphenylylmethyl-quinazolin-4-one derivatives as angiotensin II AT1 receptor antagonists. J Med Chem 49:1526–1535. doi:10.1021/jm050232e

    Article  CAS  PubMed  Google Scholar 

  8. Alanine A, Gobbi LC, Kolczewski S, Luebbers T, Peters J-U, Steward L (2006) Preparation of 8-alkoxy or cycloalkoxy-4-methyl-3,4-dihydro-quinazolin-2-ylamines for treating 5-HT5A receptor related diseases. US Patent US 2006293350, 2006.

  9. Chaturvedula PV, Chen L, Civiello R, Degnan AP, Dubowchik GM, Han X, Jiang XJJ, Macor JE, Poindexter GS, Tora GO, Luo G (2007) Preparation of piperidine-1-carboxamide derivatives and spirocycles thereof as antagonists of calcitonin gene-related peptide receptors. US Patent US20070149503A1, 2007.

  10. Prakash M, Jayakumar S, Kesavan V (2013) Investigation of the enantioselective synthesis of 2,3-dihydroquinazolinones using Sc(III)-inda-pybox. Synthesis 45:2265–2272. doi:10.1055/s-0033-1339288

    Article  CAS  Google Scholar 

  11. Sharma M, Mahar R, Shukla SK, Kant R, Chauhan PMS (2013) Potassium carbonate mediated unusual transformation of 2,3-dihydroquinazolinone via cascade reaction. Tetrahedron Lett 54:6171–6177. doi:10.1016/j.tetlet.2013.08.095

    Article  CAS  Google Scholar 

  12. Shi D, Rong L, Wang J, Zhuang Q, Wang X, Hu H (2003) Synthesis of quinazolin-4(3\(H)\)-ones and 1,2-dihydroquinazolin-4(3\(H)\)-ones with the aid of a low-valent titanium reagent. Tetrahedron Lett 44:3199–3201. doi: 10.1016/S0040-4039(03)00449-0

    Article  CAS  Google Scholar 

  13. Rueping M, Antonchick AP, Sugiono E, Grenader K (2009) Asymmetric bronsted acid catalysis: catalytic enantioselective synthesis of highly biologically active dihydroquinazolinones. Angew Chem Int Ed 48:908–910. doi:10.1002/anie.200804770

    Article  CAS  Google Scholar 

  14. Cheng X, Vellalath S, Goddard R, List B (2008) Direct catalytic asymmetric synthesis of cyclic aminals from aldehydes. J Am Chem Soc 130:15786–15787. doi:10.1021/ja8071034

    Article  CAS  PubMed  Google Scholar 

  15. Chen J, Su W, Wu H, Liu M, Jin C (2007) Eco-friendly synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones in ionic liquids or ionic liquid-water without additional catalyst. Green Chem 9:972–975. doi: 10.1039/b700957g

    Article  CAS  Google Scholar 

  16. Safari J, Gandomi-Ravandi S (2013) Microwave-accelerated three components cyclocondensation in the synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones promoted by Cu-CNTs. J Mol Catal A 371:135–140. doi: 10.1016/j.molcata.2013.01.031

    Article  CAS  Google Scholar 

  17. Sashidhara KV, Palnati GR, Dodda RP, Avula SR, Swami P (2013) One-pot regioselective synthesis of imidazole and 2,3-dihydroquinazolinone derivatives: an easy access to “nature-like molecules”; part XIII in the series: “studies on novel synthetic methodologies”. Synlett 24:1795–1800. doi:10.1055/s-0033-1339466

    Article  CAS  Google Scholar 

  18. Sharma R, Pandey AK, Chauhan PMS (2012) A greener protocol for accessing 2,3-dihydro/spiroquinazolin-\(4(1H)\)-ones: natural acid-SDS catalyzed three-component reaction. Synlett 23:2209–2214. doi: 10.1055/s-0032-1317014

    Article  CAS  Google Scholar 

  19. Ramesh K, Karnakar K, Satish G, Nageswar YVD (2012) Tandem supramolecular synthesis of substituted 2-aryl-2,3-dihydroquinazolin-\(4(1H)\)-ones in the presence of \(\beta \)-cyclodextrin in water. Tetrahedron Lett 53:6095–6099. doi: 10.1016/j.tetlet.2012.08.141

    Article  CAS  Google Scholar 

  20. Dabiri M, Salehi P, Baghbanzadeh M (2007) Ionic liquid-promoted eco-friendly and efficient synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones. Monatshefte Chem 138:1191–1194. doi:10.1007/s00706-007-0635-0

  21. Baghbanzadeh M, Salehi P, Dabiri M (2006) Kozehgary G (2006) Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-\(4(1H)\)-one derivatives. Synthesis 02:344–348. doi: 10.1055/s-2005-924766

    Google Scholar 

  22. Salehi P, Dabiri M, Zolfigol MA (2005) Baghbanzadeh M (2005) A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Synlett 07:1155–1157

    Article  Google Scholar 

  23. Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G, Mohammadi AA (2005) Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-\(4(1H)\)-ones using KAl(\(\text{ SO }_{4})_{2}\cdot 12\text{ H }_{2}\)O as a reusable catalyst in water and ethanol. Tetrahedron Lett 46:6123–6126. doi: 10.1016/j.tetlet.2005.06.157

    Article  CAS  Google Scholar 

  24. Chen J, Wu D, He F, Liu M, Wu H, Ding J, Su W (2008) Gallium(III) triflate-catalyzed one-pot selective synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones and quinazolin-4(3\(H)\)-ones. Tetrahedron Lett 49:3814–3818. doi: 10.1016/j.tetlet.2008.03.127

    Article  CAS  Google Scholar 

  25. Zhang J, Ren D, Ma Y, Wang W, Wu H (2014) CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol. Tetrahedron 70:5274–5282. doi: 10.1016/j.tet.2014.05.059

    Article  CAS  Google Scholar 

  26. Guggenheim KG, Toru H, Kurth MJ (2012) One-pot, two-step cascade synthesis of quinazolinotriazolobenzodiazepines. Org Lett 14:3732–3735. doi:10.1021/ol301592z

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  27. Wang X-S, Yang K, Zhou J, Tu S-J (2010) Facile method for the combinatorial synthesis of 2,2-disubstituted quinazolin-\(4(1H)\)-one derivatives catalyzed by iodine in ionic liquids. J Comb Chem 12:417–421. doi: 10.1021/cc900174p

    Article  CAS  PubMed  Google Scholar 

  28. Rivero IA, Espinoza K, Somanathan R (2004) Syntheses of quinazoline-2,4-dione alkaloids and analogues from Mexican Zanthoxylum species. Molecules 9:609–616. doi:10.3390/90700609

  29. Dabiri M, Salehi P, Mohammadi AA, Baghbanzadeh M (2004) Kozehgiry G (2004) Montmorillonite K-10 catalyzed solvent-free synthesis of 2,3-disubstituted-4(3\(H)\)-quinazolinones under microwave irradiation. J Chem Res 8:570–572. doi:10.3184/0308234042563866

  30. Wu J, Du X, Ma J, Zhang Y, Shi Q, Luo L, Song B, Yang S, Hu D (2014) Preparation of 2,3-dihydroquinazolin-\(4(1H)\)-one derivatives in aqueous media with \(\beta \) -cyclodextrin-\(\text{ SO }_{3}\)H as a recyclable catalyst. Green Chem 16:3210–3217. doi: 10.1039/c3gc42400f

    Article  CAS  Google Scholar 

  31. Narasimhulu M, Lee YR (2011) Ethylenediamine diacetate-catalyzed three-component reaction for the synthesis of 2,3-dihydroquinazolin-\(4(1H)\)-ones and their spirooxindole derivatives. Tetrahedron 67:9627–9634. doi: 10.1016/j.tet.2011.08.018

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a Yeungnam University Research Grant (214A380008).

Author information

Authors and Affiliations

  1. School of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea

    Xiaoyan Zhu, So Rang Kang, Likai Xia, Jihye Lee, Nagaraj Basavegowda & Yong Rok Lee

Authors
  1. Xiaoyan Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. So Rang Kang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Likai Xia
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jihye Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Nagaraj Basavegowda
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yong Rok Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yong Rok Lee.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (doc 7028 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhu, X., Kang, S.R., Xia, L. et al. Efficient \(\hbox {Cu(OTf)}_{2}\)-catalyzed synthesis of novel and diverse 2,3-dihydroquinazolin-4(1\(H\))-ones. Mol Divers 19, 67–75 (2015). https://doi.org/10.1007/s11030-014-9557-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-014-9557-z

Keywords

Search

Navigation