Advertisement

Molecular Diversity

, Volume 21, Issue 4, pp 865–873 | Cite as

Effective DABCO-catalyzed synthesis of new tetrazolo[1,5-a]pyrimidine analogs

  • Ramin Ghorbani-VagheiEmail author
  • Azadeh Shahriari
  • Jafar Mahmoodi
  • Yaser Maghbooli
Original Article
  • 200 Downloads

Abstract

In this study, an efficient multicomponent one-pot route is described for the DABCO-catalyzed synthesis of tetrazolo[1,5-a]pyrimidines. This synthesis strategy is based on the reaction of malononitrile and aldehydes with 5-aminotetrazole monohydrate using 1,4-diazabicyclo[2.2.2]octane (DABCO) in i-PrOH under reflux conditions. This protocol is a simple, green, and low-cost technique to prepare new compounds with potential medicinal properties.

Graphical Abstract

Keywords

DABCO Tetrazolo[1, 5-a]pyrimidines Multicomponent MCRs One-pot 5-aminotetrazole monohydrate 

Notes

Acknowledgements

We would like to thank Bu-Ali Sina University, Center of Excellence in Developmental of Environmentally Friendly Methods for Chemical Synthesis (CEDEFMCS) for financial support of this study.

Supplementary material

11030_2017_9760_MOESM1_ESM.docx (4.1 mb)
Supplementary material 1 (docx 4201 KB)
11030_2017_9760_MOESM2_ESM.docx (4.3 mb)
Supplementary material 2 (docx 4428 KB)

References

  1. 1.
    Meng W, Hamann LG, Brigance RP (2006) Azolopyrimidine-based inhibitors of dipeptidyl peptidase iv and methods. Patent WO2006071752 A1Google Scholar
  2. 2.
    Desenko SM, Lipson VV, Gorbenko NI, Pivovarevich LP, Ryndina EN, Moroz VV, Varavin VP (1995) Synthesis and hypoglucamic activity of azolopyrimidine derivatives. ChemInform 4:265–266. doi: 10.1002/chin.199544165 Google Scholar
  3. 3.
    Dietz J, Grammenos W, Muller B, Lohmann J, Renner J, Ulmschneider S, Vrettou M (2008) Fungizide azolopyrimidine. verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel. Patent WO2008006761 A1Google Scholar
  4. 4.
    Grammenos W, Grote T, Huenger U, Lohmann J, Mueller B, Rack M, Rheinheimer J, Schaefer P, Schwoegler A (2006) 2-substituted 7-amino-azolopyrimidine, a method for the production and use thereof for controlling pathogenic fungi and agents containing said compound. Patent WO2006092428 A3Google Scholar
  5. 5.
    Schwogler A, Gewehr M, Muller B, Grote T, Grammenos W, Blasco J, Rheinheimer J, Blettner C, Schafer P, Schieweck F, Wagner O, Stierl R, Schofl U, Strathmann S, Scherer M (2007) Azolopyrimidine compounds and use thereof for combating parasitic fungi. Patent US20070197389 A1Google Scholar
  6. 6.
    Sirakanyan S, Geronikaki A, Spinelli D, Hovakimyan A, Noravyan A (2013) Synthesis and structure of condensed triazolo- and tetrazolopyrimidines. Tetrahedron 69:10637–10643. doi: 10.1016/j.tet.2013.10.015 CrossRefGoogle Scholar
  7. 7.
    Hussein A, Ahmed OM (2010) Regioselective one-pot synthesis and anti-proliferative and apoptotic effects of some novel tetrazolo[1,5-a]pyrimidine derivatives. Bioorg Med Chem 18:2639–2644. doi: 10.1016/j.bmc.2010.02.028 CrossRefPubMedGoogle Scholar
  8. 8.
    Dougherty A, Guo H, Westby G, Liu Y, Simsek E, Guo J, Mehta A, Norton P, Gu B, Cuconati A (2007) A substituted tetrahydro-tetrazolo-pyrimidine is a specific and novel inhibitor of hepatitis B virus surface antigen secretion. Antimicrob Agents Ch 51:4427–4437. doi: 10.1128/AAC.00541-07 CrossRefGoogle Scholar
  9. 9.
    Yu W, Goddard C, Clearfield E, Mills C, Xiao T, Guo H, Morrey JD, Motter NE, Zhao K, Block TM, Cuconati A (2011) Design synthesis, and biological evaluation of triazolo-pyrimidine derivatives as novel inhibitors of hepatitis B virus surface antigen (HBsAg) secretion. J Med Chem 16:5660–5670. doi: 10.1021/jm200696v CrossRefGoogle Scholar
  10. 10.
    Ahmed E, Ameen M, Abdel-latif F (2006) Heterocyclization of orthoaminoester and orthoa minonitrilethieno[2,3- c]pyridine: The facile synthesis of fused pyridothienopyrimidines. Phosphorus Sulfur 181:497–510. doi: 10.1080/10426500500263748 CrossRefGoogle Scholar
  11. 11.
    Sharma RL, Kumar S, Sachar A, Singh J, Kour D (2005) Synthesis of 1,2,4-triazolo, tetrazolo and pyrazolylquinazolines. Ind J Heterocycl Chem 15:101–104Google Scholar
  12. 12.
    Abdelhamid AO, Al-Atoom AA (2005) 2-[4-(2-Thienyl)-1,3-thiazol-2-yl]ethanenitrile in heterocyclic synthesis of biological interist. Phosphorus Sulfur 180:1629–1646. doi: 10.1080/104265090885048 CrossRefGoogle Scholar
  13. 13.
    Abdel-Hafez SH (2005) Selenium-containing heterocycles. synthesis and reactions of 2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carbonitrile with anticipated biological activity. Russ J Org Chem 41:396–401. doi: 10.1007/s11178-005-0177-z CrossRefGoogle Scholar
  14. 14.
    Daboun H, El-Reedy AA (1983) One step synthesis of new 4-aminopyrimidine derivatives: preparation of tetrazolo- and s-triazolopyrimidines. ChemInform 13:1686–1689. doi: 10.1515/znb-1983-1223 Google Scholar
  15. 15.
    Bhuyan P, Lekhok K, Sandhu J (1999) Studies on uracils: synthesis of tetrazolo[4 0,5 0:1,6]pyrido[2,3-d ]pyrimidines by the action of cyano stabilised carbanions on 6-azido-5-formyluracils. J Chem Res. doi: 10.1039/A808470J Google Scholar
  16. 16.
    Chebanov VA, Desenko SM, Sakhno Y, Panchenko ES, Saraev VE, Musatov VI, Konev VF (2002) Heterocyclization products of arylidenepyruvic acids with 5-aminotetrazole and 2-aminobenzimidazol. Fiziol Akt Rechovini 2:10–12Google Scholar
  17. 17.
    Desenko SM, Gladkov ES, Komykhov SA, Shishkin O, Orlov VD (2001) Partially hydrogenated aromatic substituted tetrazolo[1,5-a]pyrimidines. Chem Heterocycl Compd 37:747–754. doi: 10.1023/A:1011925631511 CrossRefGoogle Scholar
  18. 18.
    Metwally MA, El-Hussiny MS, El-Ablak FZ, Khalil AM (1989) Synthesis of some heterocycles of pharmaceutical interests. Pharmazie 44:261–265PubMedGoogle Scholar
  19. 19.
    Hussein A (2010) Synthesis of some new purine-related compounds: Regioselective one-pot synthesis of new tetrazolo[1,5-a]pyrimidine, pyrazolo[1,5-a]pyrimidine and pyrimido[1,6-a]pyrimidine derivatives. J Saudi Chem Soc 14:61–68. doi: 10.1016/j.jscs.2009.12.010 CrossRefGoogle Scholar
  20. 20.
    Raju C, Madhaiyan K, Uma R, Sridhar R, Ramakrishna S (2012) Antimicrobial and antioxidant activity evaluation of tetrazolo[1,5-a]pyrimidines: a simple diisopropyl ammonium trif luoroacetate mediated synthesis. RSC Adv 31:11657–11663. doi: 10.1039/C2RA21330C CrossRefGoogle Scholar
  21. 21.
    Yao C, Lei S, Wang C, Yu C, Tu S (2008) Solvent-free synthesis of 5-methyl-7-aryl-4, 7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters catalyzed by sulfamic acid. J Heterocycl Chem 6:1609–1613. doi: 10.1002/jhet.5570450609 CrossRefGoogle Scholar
  22. 22.
    Shen S, Zhang H, Yu C, Yao C, Li T, Qin B, Lu J, Wang D (2013) Solvent-free combinatorial synthesis of tetrazolo[1,5-a]thiopyrano[3,4-d]pyrimidine derivatives. Res Chem Intermed 4:1799–1806. doi: 10.1007/s11164-012-0714-7 CrossRefGoogle Scholar
  23. 23.
    Metwally MA, El-Hussiny MS, El-Ablak FZ, Khalil AM (1989) Synthesis of some heterocycles of pharmaceutical interest. Die Pharmazie 4:261–265Google Scholar
  24. 24.
    Zeng LY, Cai C (2009) Iodine catalyzed one-pot multicomponent synthesis of a library of compounds containing tetrazolo[1,5-a]pyrimidine core. J Comb Chem 12:35–40. doi: 10.1021/cc9000983 CrossRefGoogle Scholar
  25. 25.
    Yang H, Tian R, Li Y (2008) Organic reactions catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO). Front Chem China 3:279–287. doi: 10.1007/s11458-008-0049-5 CrossRefGoogle Scholar
  26. 26.
    Bita B (2010) 1,4-Diazabicyclo[2.2.2]octane (DABCO) as a useful catalyst in organic synthesis. Eur J Chem 1:54–60. doi: 10.5155/eurjchem.1.1.54-60.2 CrossRefGoogle Scholar
  27. 27.
    Dalko PI, Moisan L (2001) Asymmetrische Organokatalyse. Angew Chem 20:3840–3864. doi: 10.1002/1521-3757(20011015)113:20<384020
  28. 28.
    Dalko PI, Moisan L (2004) Im Goldenen Zeitalter der Organokatalyse. Angew Chem 39:5248–5286. doi: 10.1002/ange.200400650 CrossRefGoogle Scholar
  29. 29.
    Ghorbani-Vaghei R, Rahmatpour F, Sarmast N, Mahmoudi J, Shahriari A (2017) DABCO as a green catalyst for the synthesis of pyranoquinoline derivatives. Can J Chem 999:1–4. doi: 10.1139/cjc-2016-0537 Google Scholar
  30. 30.
    Jain S, Paliwal PK, Babu GN, Bhatewara A (2014) DABCO promoted one-pot synthesis of dihydropyrano (c) chromene and pyrano[2,3-d]pyrimidine derivatives and their biological activities. J Saudi Chem Soc 5:535–540. doi: 10.1016/j.jscs.2011.10.023
  31. 31.
    Singh M, Fatma S, Ankit P, Singh SB, Singh J (2014) Boric acid in aqueous micellar medium: an effective and recyclable catalytic system for the synthesis of aryl-7,8-dihydro [1,2,4]triazolo[4,3-a]pyrimidine-6-carbonitriles. Tetrahedron Lett 2:525–527. doi: 10.1016/j.tetlet.2013.11.090 CrossRefGoogle Scholar
  32. 32.
    Kappe T, Roschger P, Farber G (1993) Synthesis and reactions of tetrazolo[1,5-\(\alpha \)] pyrimidines. J Heterocycl Chem 5:1267–1271. doi: 10.1002/jhet.5570300516 CrossRefGoogle Scholar
  33. 33.
    Tisler M (1973) Some aspects of azido-tetrazolo isomerization. Synthesis 3:123–126. doi: 10.1055/s-1973-22145 CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2017

Authors and Affiliations

  • Ramin Ghorbani-Vaghei
    • 1
    Email author
  • Azadeh Shahriari
    • 1
  • Jafar Mahmoodi
    • 1
  • Yaser Maghbooli
    • 1
  1. 1.Department of Organic Chemistry, Faculty of ChemistryBu-Ali Sina UniversityHamedanIran

Personalised recommendations