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Regioselective synthesis and theoretical studies of novel bis(tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-ones) catalyzed by ZnO nanoparticles

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Abstract

A novel series of bis(tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-ones) were prepared in a regioselective manner via a three component reaction of bis-aldehydes with 5-amino-1,2,4-triazole and dimedone under microwave irradiation as well as under conventional heating. The reactions were carried out in the absence as well as in the presence of ZnO nanoparticles as a heterogeneous catalyst. Best results were achieved when these reactions were carried out under MW heating. The presence of ZnO nanoparticles was found to improve the yields of the reactions but did not change the regioselectivity the products. The reaction mechanism and the unambiguous structural elucidation of the expected regioisomers were studied using DFT calculations as well as 2D-HMBC spectroscopy.

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References

  1. Bossert F, Vater W (1989) Med Res Rev 9:291

    Article  CAS  Google Scholar 

  2. Triggle DJ, Langs DA, Janis RA (1989) Med Res Rev 9:123

    Article  CAS  Google Scholar 

  3. Alajarin R, Alvarez-Builla J, Vaquero JJ, Sunkel C, Fau de Casa-Juana M, Statkow PR, Sanz-Aparicio J (1993) Tetrahedron Asymmetry 4:617

    Article  CAS  Google Scholar 

  4. Shaaban MR, Saleh TS, Mayhoub AS, Farag AM (2011) Eur J Med Chem 46:3690

    Article  CAS  Google Scholar 

  5. Theivendren Panneer S, Caiado Richa J, Phadte Vijaysarathy Dniandev SKV (2015) Res Pharm 2:1

    Google Scholar 

  6. Jackman AL, Taylor GA, Gibson W, Kimbell R, Brown M, Calvert AH, Judson IR, Hughes LR (1991) Cancer Res 51:5579

    CAS  Google Scholar 

  7. Witt A, Bergman J (2003) Curr Org Chem 7:659

    Article  CAS  Google Scholar 

  8. Jones TR, Calvert AH, Jackman AL, Brown SJ, Jones M, Harrap KR (1981) Eur J Cancer 17:11

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  10. Vansteenkiste JF (2004) Expert Rev Anticancer Ther 4:5

    Article  CAS  Google Scholar 

  11. Tiseo M, Loprevite M, Ardizzoni A (2004) Curr Med Chem Agents 4:139

    Article  CAS  Google Scholar 

  12. Dickinson RP, Bell AS, Hitchcock CA, Narayanaswami S, Ray SJ, Richardson K, Troke PF (1996) Bioorg Med Chem Lett 6:2031

    Article  CAS  Google Scholar 

  13. Ulusoy N, Gürsoy A, Ötük G (2001) Farm 56:947

    Article  CAS  Google Scholar 

  14. El-Gohary NS (2013) Med Chem Res 22:5236

    Article  CAS  Google Scholar 

  15. Abdelhamid IA, Abdelmoniem AM, Ghozlan SAS, Butenschön H (2016) J Heterocycl Chem 53:1251

    Article  CAS  Google Scholar 

  16. Palaska E, Şahin G, Kelicen P, Durlu NT, Altinok G (2002) Farm 57:101

    Article  CAS  Google Scholar 

  17. Nagai S-I, Takemoto S, Ueda T, Mizutani K, Uozumi Y, Tokuda H (2001) J Heterocycl Chem 38:1097

    Article  CAS  Google Scholar 

  18. Xu Z, Martinez-Ariza G, Cappelli AP, Roberts SA, Hulme C (2015) J Org Chem 80:9007

    Article  CAS  Google Scholar 

  19. Hazra A, Bharitkar YP, Chakraborty D, Mondal SK, Singal N, Mondal S, Maity A, Paira R, Banerjee S, Mondal NB (2013) ACS Comb Sci 15:41

    Article  CAS  Google Scholar 

  20. Liu H, Dou G, Shi D (2010) J Comb Chem 12:292

    Article  CAS  Google Scholar 

  21. Dömling A, Wang W, Wang K (2012) Chem Rev 112:3083

    Article  Google Scholar 

  22. Raasch A, Scharfenstein O, Tränkle C, Holzgrabe U, Mohr K (2002) J Med Chem 45:3809

    Article  CAS  Google Scholar 

  23. Jain M, Sakhuja R, Khanna P, Bhagat S, Jain S (2008) Arkivoc 2008:54

    Google Scholar 

  24. Yang GY, Oh K-A, Park N-J, Jung Y-S (2007) Bioorg Med Chem 15:7704

    Article  CAS  Google Scholar 

  25. Di Giacomo B, Bedini A, Spadoni G, Tarzia G, Fraschini F, Pannacci M, Lucini V (2007) Bioorg Med Chem 15:4643

    Article  Google Scholar 

  26. Wang C, Jung G-Y, Hua Y, Pearson C, Bryce MR, Petty MC, Batsanov AS, Goeta AE, Howard JAK (2001) Chem Mater 13:1167

    Article  CAS  Google Scholar 

  27. Wang C, Jung G-Y, Batsanov AS, Bryce MR, Petty MC (2002) J Mater Chem 12:173

    Article  CAS  Google Scholar 

  28. Polshettiwar V, Varma RS (2008) Chem Soc Rev 37:1546

    Article  CAS  Google Scholar 

  29. Oliver Kappe C (2008) Chem Soc Rev 37:1127

    Article  CAS  Google Scholar 

  30. Polshettiwar V, Varma RS (2008) Acc Chem Res 41:629

    Article  CAS  Google Scholar 

  31. Dallinger D, Kappe CO (2007) Chem Rev 107:2563

    Article  CAS  Google Scholar 

  32. Bollini M, González M, Bruno AM (2009) Tetrahedron Lett 50:1507

    Article  CAS  Google Scholar 

  33. Wang D, Astruc D (2014) Chem Rev 114:6949

    Article  CAS  Google Scholar 

  34. Baeza A, Guillena G, Ramón DJ (2016) ChemCatChem 8:49

    Article  CAS  Google Scholar 

  35. Shylesh S, Schünemann V, Thiel WR (2010) Angew Chem Int Ed 49:3428

    Article  CAS  Google Scholar 

  36. Shirini F, Abedini M (2013) J Nanosci Nanotechnol 13:4838

    Article  CAS  Google Scholar 

  37. Elwahy AHM, Shaaban MR (2015) RSC Adv 5:75659

    Article  CAS  Google Scholar 

  38. Banerjee S, Saha A (2013) New J Chem 37:4170

    Article  CAS  Google Scholar 

  39. Rao G, Kaushik M, Halve A (2012) Tetrahedron Lett 53:2741

    Article  Google Scholar 

  40. Bhattacharyya P, Pradhan K, Paul S, Das A (2012) Tetrahedron Lett 53:4687

    Article  CAS  Google Scholar 

  41. Ghozlan SAS, Abdelhamid IA, Hassaneen HM, Elnagdi MH (2007) J Heterocycl Chem 44:105

    Article  CAS  Google Scholar 

  42. Ghozlan SAS, Abdelhamid IA, Elnagdi MH (2006) Arkivoc 2006:147

    Google Scholar 

  43. Abdelhamid IA (2008) Synlett 2008:625

    Google Scholar 

  44. Ghozlan SAS, Mohamed MH, Abdelmoniem AM, Abdelhamid IA (2009) Arkivoc 2009:302

    Google Scholar 

  45. Abdelhamid IA, Darwish ES, Nasra MA, Abdel-Gallil FM, Fleita DH (2010) Synthesis:1107

  46. Elwahy AHM, Ahmed MM, El-sadek M (2001) J Chem Res 2001:175

    Article  Google Scholar 

  47. Salama SK, Darweesh AF, Abdelhamid IA, Elwahy AHM (2017) J Heterocycl Chem 54:305

    Article  CAS  Google Scholar 

  48. Mohamed MF, Darweesh AF, Elwahy AHM, Abdelhamid IA (2016) RSC Adv 6:40900

    Article  CAS  Google Scholar 

  49. Abdelhamid IA, Darweesh AF, Elwahy AHM (2015) Tetrahedron Lett 56:7085

    Article  CAS  Google Scholar 

  50. Kassab RM, Elwahy AHM, Abdelhamid IA (2016) Monatsh Chem 147:1227

    Article  CAS  Google Scholar 

  51. Sanad SMH, Kassab RM, Abdelhamid IA, Elwahy AHM (2016) Heterocycles 92:910

    Article  CAS  Google Scholar 

  52. Chebanov VA, Gura KA, Desenko SM (2010) Top Heterocycl Chem 23:41

    CAS  Google Scholar 

  53. Hassaneen HME, Abdelhamid IA (2013) Curr Org Synth 10:953

    Google Scholar 

  54. Lloyd J, Finlay HJ, Atwal K, Kover A, Prol J, Yan L, Bhandaru R, Vaccaro W, Huynh T, Huang CS, Conder M, Jenkins-West T, Sun H, Li D, Levesque P (2009) Bioorg Med Chem Lett 19:5469

    Article  CAS  Google Scholar 

  55. Lloyd J, Finlay HJ, Vacarro W, Hyunh T, Kover A, Bhandaru R, Yan L, Atwal K, Conder ML, Jenkins-West T, Shi H, Huang C, Li D, Sun H, Levesque P (2010) Bioorg Med Chem Lett 20:1436

    Article  CAS  Google Scholar 

  56. Vaccaro W, Huynh T, Lloyd J, Atwal K, Finlay HJ, Levesque P, Conder ML, Jenkins-West T, Shi H, Sun L (2008) Bioorg Med Chem Lett 18:6381

    Article  CAS  Google Scholar 

  57. Suresh, Sandhu JS (2012) Arkivoc 2012:66

    Google Scholar 

  58. Harwood Ellis (1992) Solid supports and catalysts in organic synthesis. Ellis Horwood and Prentice Hall Organic Chemistry Series, London

    Google Scholar 

  59. Varma RS (1999) Green Chem 1:43

    Article  CAS  Google Scholar 

  60. Hosseini-Sarvari M, Tavakolian M (2012) Appl Catal A Gen 441:65

    Article  Google Scholar 

  61. Kong XY, Wang ZL (2003) Nano Lett 3:1625

    Article  CAS  Google Scholar 

  62. Krishnamurthy G, Jagannath KV (2013) J Chem Sci 125:807

    Article  CAS  Google Scholar 

  63. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03, Rev A.1. Gaussian, Inc, Pittsburgh PA

  64. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  65. Becke AD (1993) J Chem Phys 98:5648

    Article  CAS  Google Scholar 

  66. Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J (1988) J Chem Phys 89:2193

    Article  CAS  Google Scholar 

  67. Dolzhenko AV, Pastorin G, Dolzhenko AV, Chui WK (2009) Tetrahedron Lett 50:2124

    Article  CAS  Google Scholar 

  68. Shneine JK, Alaraji YH (2013) Int J Sci Res 14611:2319

    Google Scholar 

  69. Albert A, Taylor PJ (1989) J Chem Soc Perkin Trans 2:1903

    Article  Google Scholar 

  70. Dabbagh HA, Rasti E, Najafi Chermahini A (2010) J Mol Struct (Theochem) 947:92

    Article  CAS  Google Scholar 

  71. Balabin RM (2009) J Chem Phys 131:154307

    Article  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt

    Nesma A. Abd El-Fatah, Ahmed F. Darweesh, Ismail A. Abdelhamid & Ahmed H. M. Elwahy

  2. Chemistry Department, Faculty of Science, Helwan University, Cairo, Egypt

    Adel A. Mohamed & Ahmed H. M. Elwahy

Authors
  1. Nesma A. Abd El-Fatah
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  2. Ahmed F. Darweesh
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  3. Adel A. Mohamed
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  4. Ismail A. Abdelhamid
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  5. Ahmed H. M. Elwahy
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Correspondence to Ismail A. Abdelhamid or Ahmed H. M. Elwahy.

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El-Fatah, N.A.A., Darweesh, A.F., Mohamed, A.A. et al. Regioselective synthesis and theoretical studies of novel bis(tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-ones) catalyzed by ZnO nanoparticles. Monatsh Chem 148, 2107–2122 (2017). https://doi.org/10.1007/s00706-017-2040-7

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