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Green synthesis of benzimidazoloquinazolines and 1,4-dihydropyridines using magnetic cyanoguanidine-modified chitosan as an efficient heterogeneous nanocatalyst under various conditions

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Abstract

In the present study, we demonstrated the synthesis of magnetic cyanoguanidine-modified chitosan (MCGC) as an efficient and green retrievable heterogeneous nanocatalyst for one-pot three-component synthesis of benzimidazoloquinazolines (from 2-aminobenzimidazole, aromatic aldehydes, and dimedone) and 1,4-dihydropyridines (via Hantzsch-type condensation of ethyl acetoacetate, aromatic aldehydes, and ammonium acetate) under the ultrasonic irradiation and reflux conditions. The structure of the catalyst was fully confirmed using Fourier transform infrared spectroscopy, vibrating sample magnetometer, field emission scanning electron microscopy, energy dispersive spectroscopy, and thermogravimetric analysis. Increased amount of amino groups that are generated by modifying the surface of chitosan with cyanoguanidine as well as presence of hydroxyl groups determined the catalytic activity of MCGC. Furthermore, as experimental results confirmed, the ultrasonic-promoted reactions gave the better results in terms of reaction time, yield, and purity of isolated products. Cost effectiveness, mild conditions, low catalyst loading, convenient work-up, and ecofriendly solvent are some of the remarkable advantages of this protocol.

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References

  1. Guin D, Baruwati B, Manorama SV (2007) Org Lett 9:1419

    CAS  PubMed  Google Scholar 

  2. Sadeghzadeh SM (2016) Catal Lett 146:2555

    CAS  Google Scholar 

  3. Samoilova N, Krayukhina M, Naumkin A, Yamskov I (2018) Monatsh Chem 149:1179

    CAS  Google Scholar 

  4. Kasprzak A, Bystrzejewski M, Poplawska M (2018) Dalton Trans 47:6314

    CAS  PubMed  Google Scholar 

  5. Anastas P, Eghbali N (2010) Chem Soc Rev 39:301

    CAS  Google Scholar 

  6. Pourjavadi A, Motamedi A, Hosseini SH, Nazari M (2016) RSC Adv 6:19128

    CAS  Google Scholar 

  7. Li D-D, Zhang J-W, Cai C (2018) Catal Commun 103:47

    CAS  Google Scholar 

  8. Dekamin MG, Azimoshan M, Ramezani L (2013) Green Chem 15:811

    CAS  Google Scholar 

  9. Shaabani A, Hezarkhani Z, Badali E (2015) RSC Adv 5:61759

    CAS  Google Scholar 

  10. Rao SN, Mohan DC, Adimurthy S (2014) Green Chem 16:4122

    Google Scholar 

  11. Shen C, Qiao J, Zhao L, Zheng K, Jin J, Zhang P (2017) Catal Commun 92:114

    CAS  Google Scholar 

  12. Lal J, Gupta SK, Agarwal DD (2012) Catal Commun 27:38

    CAS  Google Scholar 

  13. Zeng M, Zhang X, Shao L, Qi C, Zhang XM (2012) J Organomet Chem 704:29

    CAS  Google Scholar 

  14. Sudheesh N, Sharma SK, Shukla RS (2010) J Mol Catal A Chem 321:77

    CAS  Google Scholar 

  15. Kühbeck D, Saidulu G, Reddy KR, Díaz DD (2012) Green Chem 14:378

    Google Scholar 

  16. Abdelhamid IA (2009) Synlett 2009:625

    Google Scholar 

  17. Makhubela BC, Jardine A, Smith GS (2011) Appl Catal A 393:231

    CAS  Google Scholar 

  18. Bao Y, Shao L, Xing G, Qi C (2019) Int J Biol Macromol 130:203

    CAS  PubMed  Google Scholar 

  19. Saikia G, Ahmed K, Gogoi SR, Sharma M, Talukdar H, Islam NS (2019) Polyhedron 159:192

    CAS  Google Scholar 

  20. Rangraz Y, Nemati F, Elhampour A (2018) Int J Biol Macromol 117:820

    CAS  PubMed  Google Scholar 

  21. Chtchigrovsky M, Primo A, Gonzalez P, Molvinger K, Robitzer M, Quignard F, Taran F (2009) Angew Chem Int Ed 48:5916

    CAS  Google Scholar 

  22. Lee M, Chen B-Y, Den W (2015) Appl Sci 5:1272

    CAS  Google Scholar 

  23. Tap H, Sugimoto R (2018) Appl Surf Sci 434:188

    Google Scholar 

  24. Kumar S, Deepak V, Kumari M, Dutta P (2016) Int J Biol Macromol 84:349

    CAS  PubMed  Google Scholar 

  25. Zhai X, Sun P, Luo Y, Ma C, Xu J, Liu W (2011) J Appl Polym Sci 121:3569

    CAS  Google Scholar 

  26. Maleki A, Firouzi-Haji R, Hajizadeh Z (2018) Int J Biol Macromol 116:320

    CAS  PubMed  Google Scholar 

  27. Ramezanpour S, Panahi A, Rominger F (2018) Monatsh Chem 149:625

    CAS  Google Scholar 

  28. Palermo V, Sathicq ÁG, Constantieux T, Rodríguez J, Vázquez PG, Romanelli GP (2016) Catal Lett 146:1634

    CAS  Google Scholar 

  29. Neochoritis CG, Zhao T, Dömling A (2019) Chem Rev 119:1970

    CAS  PubMed  PubMed Central  Google Scholar 

  30. Dömling A (2006) Chem Rev 106:17

    PubMed  Google Scholar 

  31. Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M, Ross G (2008) Synthesis 2008:4007

    Google Scholar 

  32. Mamaghani M, Tabatabaeian K, Shirini F, Rassa M (2012) Bioorg Med Chem Lett 22:5956

    PubMed  Google Scholar 

  33. Dandia A, Singh R, Bhaskaran S, Samant SD (2011) Green Chem 13:1852

    CAS  Google Scholar 

  34. Wu C, Lu L-H, Peng A-Z, Jia G-K, Peng C, Cao Z, Tang Z, He W-M, Xu X (2018) Green Chem 20:3683

    CAS  Google Scholar 

  35. Mason TJ (1997) Chem Soc Rev 26:443

    CAS  Google Scholar 

  36. O’Hagan D (2000) Nat Prod Rep 17:435

    PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  38. Alagarsamy V (2004) Pharmazie 59:753

    CAS  PubMed  Google Scholar 

  39. Alagarsamy V, Murugananthan G, Venkateshperumal R (2003) Biol Pharm Bull 26:1711

    CAS  PubMed  Google Scholar 

  40. Hour M-J, Huang L-J, Kuo S-C, Xia Y, Bastow K, Nakanishi Y, Hamel E, Lee K-H (2000) J Med Chem 43:4479

    CAS  PubMed  Google Scholar 

  41. Alagarsamy V, Revathi R, Meena S, Ramaseshu K, Rajasekaran S, De Clerco E (2004) Indian J Pharm Sci 66:459

    CAS  Google Scholar 

  42. Smutny T, Nova A, Drechslerová M, Carazo A, Hyrsova L, Kunes J, Pour M, Špulák M, Pavek P (2016) J Med Chem 59:4601

    CAS  PubMed  Google Scholar 

  43. Ahmad I (2017) MedChemComm 8:871

    PubMed  PubMed Central  Google Scholar 

  44. Tebbe MJ, Spitzer WA, Victor F, Miller SC, Lee CC, Sattelberg TR, McKinney E, Tang JC (1997) J Med Chem 40:3937

    CAS  PubMed  Google Scholar 

  45. Charifson PS, Grillot AL, Grossman TH, Parsons JD, Badia M, Bellon S, Deininger DD, Drumm JE, Gross CH, LeTiran A (2008) J Med Chem 51:5243

    CAS  PubMed  Google Scholar 

  46. White AW, Almassy R, Calvert AH, Curtin NJ, Griffin RJ, Hostomsky Z, Maegley K, Newell DR, Srinivasan S, Golding BT (2000) J Med Chem 43:4084

    CAS  PubMed  Google Scholar 

  47. Naesdal J, Bodemar G, Walan A (1984) Scand J Gastroenterol 19:916

    CAS  PubMed  Google Scholar 

  48. Kamali F, Shirini F (2017) New J Chem 41:11778

    CAS  Google Scholar 

  49. Sheldon R, Arends A, Hanefeld U (2007) Green chemistry and catalysis. Wiley, VCH Verlag GmbH and Co KgaA, Weinheim

    Google Scholar 

  50. Heravi MM, Derikvand F, Ranjbar L (2010) Synth Comm 40:677

    CAS  Google Scholar 

  51. Gajaganti S, Kumari S, Kumar D, Allam BK, Srivastava V, Singh S (2018) J Heterocycl Chem 55:2578

    CAS  Google Scholar 

  52. Boecker RH, Guengerich FP (1986) J Med Chem 29:1596

    CAS  Google Scholar 

  53. Sirisha K, Bikshapathi D, Achaiah G, Reddy VM (2011) Eur J Med Chem 46:1564

    CAS  PubMed  Google Scholar 

  54. Klusa V (1995) Drugs Future 20:135

    Google Scholar 

  55. Bretzel RG, Bollen CC, Maeser E, Federlin KF (1993) Am J Kidney Dis 21:S53

    Google Scholar 

  56. Janis RA, Triggle D (1983) J Med Chem 26:775

    CAS  PubMed  Google Scholar 

  57. Mager P, Coburn R, Solo A, Triggle D, Rothe H (1992) Drug Des Discov 8:273

    CAS  PubMed  Google Scholar 

  58. Itoh T, Nagata K, Miyazaki M, Ishikawa H, Kurihara A, Ohsawa A (2004) Tetrahedron 60:6649

    CAS  Google Scholar 

  59. Dondoni A, Massi A, Minghini E, Bertolasi V (2004) Tetrahedron 60:2311

    CAS  Google Scholar 

  60. Cherkupally SR, Mekala R (2008) Chem Pharm Bull 56:1002

    CAS  PubMed  Google Scholar 

  61. Safari J, Banitaba SH, Khalili SD (2011) J Mol Catal Chem 335:46

    CAS  Google Scholar 

  62. Albadi J, Shirini F, Ghabezi B, Seiadatnasab T (2017) Arab J Chem 10:S509

    CAS  Google Scholar 

  63. Dekamin MG, Kazemi E, Karimi Z, Mohammadalipoor M, Naimi-Jamal MR (2016) Int J Biol Macromol 93:767

    CAS  PubMed  Google Scholar 

  64. Mahinpour R, Moradi L, Zahraei Z, Pahlevanzadeh N (2018) J Saudi Chem Soc 22:876

    CAS  Google Scholar 

  65. Kumar P, Kadyan K, Duhan M, Sindhu J, Hussain K, Lal S (2019) Chem Pap 73:1153

    CAS  Google Scholar 

  66. Davarpanah J, Ghahremani M, Najafi O (2019) J Mol Struct 1177:525

    CAS  Google Scholar 

  67. Rekunge DS, Khatri CK, Chaturbhuj GU (2017) Tetrahedron Lett 58:1240

    CAS  Google Scholar 

  68. Khaskel A, Barman P (2016) Heteroat Chem 27:114

    CAS  Google Scholar 

  69. Aftan MM (2018) Tikrit J Pure Sci 23:83

    Google Scholar 

  70. Hemmati B, Javanshir S, Dolatkhah Z (2016) RSC Adv 6:50431

    CAS  Google Scholar 

  71. Mousavi MR, Maghsoodlou MT (2015) J Iran Chem Soc 12:743

    CAS  Google Scholar 

  72. Yao C, Lei S, Wang C, Li T, Yu C, Wang X, Tu S (2010) J Heterocycl Chem 47:26

    CAS  Google Scholar 

  73. Weber L (2002) Drug Discov Today 7:143

    CAS  PubMed  Google Scholar 

  74. Mousavi MR, Maghsoodlou MT (2014) Monatsh Chem 145:1967

    CAS  Google Scholar 

  75. Suslick KS, Hammerton DA, Cline RE (1986) J Am Chem Soc 108:5641

    CAS  Google Scholar 

  76. Tameh FA, Safaei-Ghomi J, Mahmoudi-Hashemi M, Shahbazi-Alavi H (2016) RSC Adv 6:74802

    CAS  Google Scholar 

  77. Maleki A, Rahimi J (2018) J Porous Mat 25:1789

    CAS  Google Scholar 

  78. Amoozadeh A, Rahmani S (2015) J Mol Catal A Chem 396:96

    CAS  Google Scholar 

Download references

Acknowledgements

We are thankful for the financial support from Chemical Injuries Research Center, Systems Biology and Poisonings Institute, Baqiyatallah University of Medical Sciences, Tehran, Iran.

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  1. Chemical Injuries Research Center, Systems Biology and Poisonings Institute, Baqiyatallah University of Medical Sciences, Tehran, Iran

    Kaveh Javanmiri & Ramin Karimian

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  1. Kaveh Javanmiri
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Correspondence to Ramin Karimian.

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Javanmiri, K., Karimian, R. Green synthesis of benzimidazoloquinazolines and 1,4-dihydropyridines using magnetic cyanoguanidine-modified chitosan as an efficient heterogeneous nanocatalyst under various conditions. Monatsh Chem 151, 199–212 (2020). https://doi.org/10.1007/s00706-019-02542-z

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