, Volume 12, Issue 1, pp 41–48 | Cite as

Synthesis of New 2-Amino-3-(2-Oxothiazol-Methyl)-Substituted-1,4-Naphthoquinone Derivatives Based on Silica Nanoparticles as a Reusable Heterogeneous Catalyst

  • Hassan Vasheghani Farahani
  • Mohammad BayatEmail author
  • Shima Nasri
Original Paper


A novel series of 2-amino-3-(2-oxothiazol-methyl)-substituted-1,4-naphthoquinone compounds were designed and prepared, by the three-component one-pot reaction of 2-aminothiazole, 2-hydroxy-1-4-naphthoquinone and aromatic aldehydes using of nano-SiO2 (20% mol) as an efficient Lewis acid and heterogeneous nano-catalyst in acetonitrile at room temperature in the period of time 2–5 h. Silica-based materials used for developing an environmental friendly methodology for the preparation of potential biologically active molecular scaffolds. The direction of product formation and the structure of all the synthesized compounds were identified by spectroscopic methods. The remarkable superiorities of this procedure include good yields (70–89%), use of an inexpensive and commercially available catalyst, regioselectivity and simple work-up.


2-Aminothiazole 2-amino-oxothiazol-methyl-naphthoquinone Silica-based nanoparticle Nano-SiO2 Heterogeneous catalyst 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.



  1. 1.
    Shin S, Lee H, Jeon C, Preya UH, Choi JH, Park JH (2017) Anticancer activity of 2-amino-substituted-1,4-naphthoquinone derivatives in ovarian cancer cells. Bull Kor Chem Soc 38:1411–1414CrossRefGoogle Scholar
  2. 2.
    Yildirim H, Bayrak N, Tuyun AF, Kara EM, Çelik BÖ, Gupta GK (2017) 2,3-Disubstituted-1,4-naphthoquinones containing an arylamine with trifluoromethyl group: synthesis, biological evaluation, and computational study. RSC Adv 7:25753–25764CrossRefGoogle Scholar
  3. 3.
    Desai NC, Bhatt N, Somani H, Trivedi A (2013) Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles. Eur J Med Chem 67:54–59CrossRefGoogle Scholar
  4. 4.
    Widhalm JR, Rhodes D (2016) Biosynthesis and molecular actions of specialized 1,4-naphthoquinone natural products produced by horticultural plants. Hortic Res 3:16046CrossRefGoogle Scholar
  5. 5.
    Rutherford AW, Krieger-Liszkay A (2001) Herbicide-induced oxidative stress in photosystem II. Trends Biochem Sci 26:648–653CrossRefGoogle Scholar
  6. 6.
    Tucker JH, Collinson SR (2002) Recent developments in the redox-switched binding of organic compounds. Chem Soc Rev 31:147–156CrossRefGoogle Scholar
  7. 7.
    Benites J, Valderrama JA, Bettega K, Pedrosa RC, Calderon PB, Verrax J (2010) Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents. Eur J Med Chem 45:6052–6057CrossRefGoogle Scholar
  8. 8.
    Prescott B (1969) Potential antimalarial agents. Derivatives of 2-chloro-1,4-naphthoquinone. J Med Chem 12:181–182CrossRefGoogle Scholar
  9. 9.
    Silver RF, Holmes HL (1968) Synthesis of some 1,4-naphthoquinones and reactions relating to their use in the study of bacterial growth inhibition. Can J Chem 46:1859–1864CrossRefGoogle Scholar
  10. 10.
    Oeriu I (1963) Relation between the chemical structure and antitubercular activity of various alpha-naphthoquinone derivatives. Biokhimiia (Moscow, Russia) 28:380–383Google Scholar
  11. 11.
    Clark NG (1984) The fungicidal activity of substituted 1,4-naphthoquinones. Part II: Alkoxy, phenoxy and acyloxy derivatives. Pest Manag Sci 15:235–240CrossRefGoogle Scholar
  12. 12.
    Munday R, Smith BL, Munday CM (2005) Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats. Chem Biol Interact 155:140–147CrossRefGoogle Scholar
  13. 13.
    Bayen S, Barooah N, Sarma RJ, Sen TK, Karmakar A, Baruah JB (2007) Synthesis, structure and electrochemical properties of 2,5-bis (alkyl/arylamino) 1,4-benzoquinones and 2-arylamino-1,4-naphthoquinones. Dyes Pigments 75:770–775CrossRefGoogle Scholar
  14. 14.
    Liu B, Ji SJ (2008) Facile synthesis of 2-smino-1,4-naphthoquinones catalyzed by molecular iodine under ultrasonic irradiation. Synth Commun 38:1201–1211CrossRefGoogle Scholar
  15. 15.
    Couladouros EA, Plyta ZF, Papageorgiou VP (1996) A general procedure for the efficient synthesis of (alkylamino) naphthoquinones. J Org Chem 61:3031–3033CrossRefGoogle Scholar
  16. 16.
    Singh MW, Karmakar A, Barooah N, Baruah JB (2007) Variations in product in reactions of naphthoquinone with primary amines. Beilstein J Org Chem 3:10CrossRefGoogle Scholar
  17. 17.
    Konstantinova LS, Lysov KA, Souvorova LI, Rakitin OA (2013) Synthesis of 2,3-dihydronaphtho[2,3-d][1,3]thiazole-4,9-diones and 2,3-dihydroanthra[2,3-d][1,3]thiazole-4,11-diones and novel ring contraction and fusion reaction of 3H-spiro[1,3-thiazole-2,1′-cyclohexanes]into 2,3,4,5-tetrahydro-1H-carbazole-6,11-diones. Beilstein J Org Chem 9:577–584CrossRefGoogle Scholar
  18. 18.
    Banothu J, Vaarla K, Bavantula R, Crooks PA (2014) Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature. Chin Chem Lett 25:172–175CrossRefGoogle Scholar
  19. 19.
    Mishra R, Sharma PK, Verma PK, Tomer I, Mathur G, Dhakad PK (2017) Biological potential of thiazole derivatives of synthetic origin. J Heterocycl Chem, in press 54:2103–2116CrossRefGoogle Scholar
  20. 20.
    Prajapati AK, Modi VP (2011) Synthesis and biological activity of n-[5-(4-methylphenyl) diazenyl-4-phenyl-1,3-thiazol-2-yl]benzamide derivatives. Quim Nova 34:771–774Google Scholar
  21. 21.
    Abdel-Sattar NE, El-Naggar AM, Abdel-Mottaleb MSA (2017) Novel thiazole derivatives of medicinal potential: synthesis and modeling. J Chem 2017:1–11CrossRefGoogle Scholar
  22. 22.
    Nasseri MA, Sadeghzadeh M (2013) Multi-component reaction on free nano-SiO2 catalyst: excellent reactivity combined with facile catalyst recovery and recyclability. J Chem Sci 125:537–544CrossRefGoogle Scholar
  23. 23.
    Zuliani A, Ivars F, Luque R (2018) Advances in nanocatalyst design for biofuel production. ChemCatChem 10:1968–1981CrossRefGoogle Scholar
  24. 24.
    Bhanja P, Modak A, Bhaumik A (2018) Supported porous nanomaterials as efficient heterogeneous catalysts for CO2 fixation reactions. Chem-A Eur J 24:7278–7297CrossRefGoogle Scholar
  25. 25.
    Mobinikhaledi A, Moghanian H, Pakdel S (2015) Microwave-assisted efficient synthesis of azlactone derivatives using 2-aminopyridine-functionalized sphere SiO2 nanoparticles as a reusable heterogeneous catalyst. Chin Chem Lett 26:557–563CrossRefGoogle Scholar
  26. 26.
    Shukla PK, Verma A, Pathak P (2014) A prospective study on silica based heterogeneous catalyst as modern organic synthesis tool. Arch Appl Sci Res 6:18–25Google Scholar
  27. 27.
    Sravya G, Grigory VZ, Balakrishna A, Reddy KMK, Reddy CS, Reddy GM, Reddy NB (2018) Nano-TiO2/SiO2 catalyzed synthesis, theoretical calculations and bioactivity studies of new α-aminophosphonates. Phosphorus Sulfur Silicon Relat Elem:1–6Google Scholar
  28. 28.
    Mousavi MR, Maghsoodlou MT (2015) Nano-SiO2: a green, efficient, and reusable heterogeneous catalyst for the synthesis of quinazolinone derivatives. J Iran Chem Soc 12:743–749CrossRefGoogle Scholar
  29. 29.
    Bayat M, Nasehfard H (2016) SiO2 nanoparticle-catalyzed facile and efficient one-pot synthesis of N-alkyl-2,5-bis[(E)-2-phenylvinyl]-1,3-dioxol-4-amine under solvent-free conditions. J Heterocycl Chem 53:1474–1478CrossRefGoogle Scholar
  30. 30.
    Bayat M, Hosseini FS, Nasri S (2018) An efficient one-pot synthesis of tetrahydrothiazolo [3,2-a] quinolin-6-one derivatives. J Sulfur Chem 39:99–111CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  • Hassan Vasheghani Farahani
    • 1
  • Mohammad Bayat
    • 1
    Email author
  • Shima Nasri
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceImam Khomeini International UniversityQazvinIran

Personalised recommendations