Abstract
In the present study, peptide nanofiber was used to immobilize zinc oxide. This nanoparticle was prepared through self-assembly in an aqueous solution. The structural properties of the prepared catalyst were examined by a series of techniques, such as FT-IR, EDS, SEM, TEM, XRD, ICP-OES (inductively coupled plasma optical emission spectrometry), and ultraviolet–visible (UV–Vis) spectroscopy. TEM images showed the necklace model for peptide nanofiber decorated with zinc oxide. The versatility of the method was investigated by N-arylation using reaction of amines with hydroxybenzotriazole as a novel phenylating reagent, one-pot synthesis of imidazoheterocycles by a three-component reaction of 2-aminopyridine, aldehyde, terminal alkyne and preparation of tetracyclic quinazolinone ring by one-pot reaction of isatoic anhydride, amine, and ninhydrin. High yields, low cost of catalyst, environmental friendliness, efficient recovery and recyclability of catalyst are the most important features of this catalytic system.
Graphical Abstract
Similar content being viewed by others
References
Hili R, Yudin AK (2006) Nat Chem Biol 2:284
Ruiz-Castillo P, Buchwald SL (2016) Chem Rev 116:12564
Kumar A, Bishnoi AK (2015) RSC Adv 5:20516
Aubin Y, Fischmeister C, Thomas CM, Renaud JL (2010) Chem Soc Rev 39:4130
Polprasert C, Liyanage LRJ (1996) Resour Conserv Recycl 16:213
Deep A, Kaur Bhatia R, Kaur R, Kumar S, Kumar Jain U, Singh H, Kishore Deb P (2017) Curr Top Med Chem 17:238
Starrett JE Jr, Montzka TA, Crosswell AR, Cavanagh RL (1998) J Med Chem 32:2204
Chandra Mohan D, Nageswara Rao S, Adimurthy S (2013) J Org Chem 78:1266
Reddy BS, Reddy PS, Reddy YJ, Yadav JS (2011) Tetrahedron Lett 52:5789
Guo P, Huang S, Mo J, Chen X, Jiang H, Chen W, Zhan H (2017) Catal Commun 90:43
Guchhait SK, Chandgude AL, Priyadarshani G (2012) J Org Chem 77:4438
Chernyak N, Gevorgyan V (2010) Angew Chem Int Ed 49:2743–2746
Asif M (2014) Int J Med Chem. https://doi.org/10.1155/2014/395637
Hisano T, Ichikawa M, Kito G, Nishi T (1972) Chem Pharm Bull 20:2575
Murthy NV, Nikumbh SP, Kumar SP, Chiranjeevi Y, Rao LV, Raghunadh AA (2016) Synlett 27:2362
Shen C, Man NY, Stewart S, Wu XF(2015) Org Biomol Chem 13:4422
Yao J, Yao Y (2017) Int J Hydrog Energy 42:18560
Ghorbani-Choghamarani A, Morad Pi, Tahmasbi B (2016) RSC Adv 6:56638
Scott RW, Ye H, Henriquez RR, Crooks RM (2003) Chem Mater 15:3873
Salavati H, Rasouli N (2011) Mater Res Bull 46:1853
Gong T, Qin L, Zhang W, Wan H, Lu J, Feng H (2015) J Phys Chem C 119:11544
Ghorbani-Choghamarani A, Taherinia Z (2017) Chin J Catal 38:469
Eskandari S, Guerin T, Toth I, Stephenson RJ (2017) Adv Drug Deliv Rev 110:169
Ren K, Wang Y, Sun T, Yue W, Zhang H (2017) Mater Sci Eng C 78:324
Vasita R, Katti DS (2006) Int J Nanomed 1:15
Wang W, Anderson CF, Wang Z, Wu W, Cui H, Liu CJ (2017) Chem Sci 8:3310
Maity I, Manna MK, Rasale D, Das AK (2014) ChemPlusChem 79:413
Wang C, Sun Y, Wang J, Xu H, Lu JR (2015) Chem Asian J 10:1953
Acar H, Garifullin R, Aygun LE, Okyay AK, Guler MO (2013) J Mater Chem A 1:10979
Khalily MA, Ustahuseyin O, Garifullin R, Genc R, Guler R (2012) Chem Commun 48:11358
Kim S, Cho HJ, Lee N, Lee YS, Shin DS, Lee SM (2017) RSC Adv 7:33162
Suresh J, Pradheesh G, Alexramani V, Sundrarajan M, Hong SI (2018) Adv Nat Sci 9:015008
Dhole SG, Dake SA, Prajapati TA, Helambe SN (2018) Proc Manuf 20:127
Chithra MJ, Sathya M, Pushpanathan K (2015) Acta Metall Sin (Engl Lett) 28:394
Yuan Y, Thome I, Kim SH, Chen D, Beyer A, Bonnamour J, Bolm C (2010) Adv Synth Catal 352:2892
Trofimov BA (1992) J Sulfur Chem 11:207
Mellado P, McIlwee HA, Badrossamay MR, Goss JA, Mahadevan L, Kit Parker K (2011) Appl Phys Lett 99:203107
Padron S, Fuentes A, Caruntu D, Lozano K (2013) J Appl Phys 113:024318
Golecki HM, Yuan H, Glavin C, Potter B, Badrossamay MR, Goss JA, Parker KK (2014) Langmuir 30:13369
Funding
This work was supported by Ilam University
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Taherinia, Z., Ghorbani-Choghamarani, A. & Hajjami, M. Peptide Nanofiber Templated Zinc Oxide Nanostructures as Non-precious Metal Catalyzed N-Arylation of Amines, One-Pot Synthesis of ImidazoHeterocycles and Fused Quinazolines. Catal Lett 149, 151–168 (2019). https://doi.org/10.1007/s10562-018-2580-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-018-2580-4