Iranian Journal of Chemistry

Iranian Journal of Chemistry

Simple, green and highly efficient synthesis of 2‑Amino-3-cyano‑4H‑pyrans via an Eco-Friendly Multicomponent Reaction Using Hard Coral Shell as a Novel Biomineral and Biodegradable Catalyst

Document Type : Original Article

Authors
Department of New Materials, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran
10.22036/cr.2023.393183.1214
Abstract
In this research, 4H-pyran derivatives were synthesized by an environmentally friendly three-component reaction between aldehyde, malononitrile and ethyl acetoacetate in the presence of a hard coral shell as a green and recyclable catalyst, under reflux conditions and ultrasonic waves in aqueous ethanol. To identify the main products and verify the structure used different techniques such as melting point measurement, FT-IR spectroscopy, and 1H NMR spectroscopy. Green synthesis, mild conditions, high yield, shorter reaction time, environmental compatibility, easy separation of products, and low cost are the main advantages of this method. The coral shell catalyst possesses unique characteristics such as being natural, inexpensive, non-toxic, non-volatile, biocompatible, biodegradable, easy to recycle, easy to handle and store, stable, readily available, and having easy preparation steps. The reaction process was carried out with ultrasound waves for 5 to 11 minutes, resulting in high efficiency. Therefore, considering the advantages of ultrasound waves in increasing reaction speed and efficiency, as well as the advantages of the coral shell catalyst, the proposed method is reported as a green, efficient, and effective one-step approach for the synthesis of derivatives of 4H-pyran with high therapeutic potential.

Graphical Abstract

Simple, green and highly efficient synthesis of 2‑Amino-3-cyano‑4H‑pyrans via an Eco-Friendly Multicomponent Reaction Using Hard Coral Shell as a Novel Biomineral and Biodegradable Catalyst
Keywords

Subjects


[1] M. G. Dekamin, M. Eslami, Green Chem, 16 (2014) 4914.
[2] D. Kumar, V. Buchi Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem., 44 (2009) 3805.
[3] S. Banerjee, A. Horn, H. Khatri, G. Sereda, Tetrahedron Lett., 52 (2011) 1878.
[4] J. M. Fortunak, J. Am. Chem. Soc., 132 (2010) 2846. [5] P. T. Anastas, M.M. Kirchhoff, T.C. Williamson, Appl. Catal. A, 221 (2001) 3.
[6] D. Kumar, P. Sharma, H. Singh, K. Nepali, G. Gupta, S. K. Jain, F. Ntie-Kang, Cell, 5 (2017) A498.
[7] R. Vinit, L. Jintae, Front. Chem., 8 (2020) 623.
[8] F. F. Alblewi, R. M. Okasha, Z. M. Hritani, H. M. Mohamed, M. A. A. El-Nassag, A. H. Halawa, A. Mora, A. M. Fouda, M. A. Assiri, A. M. Al-Dies, T. H. Afifi, A. M. El-Agrody, Bioorg. Chem., 87 (2019) 560.
[9] T.H. Afifi, R.M. Okasha, H.  Alsherif, H. E. Ahmed, A.S. Abd-El-Aziz, Curr. Org. Synth. 14, 1036 (2017).
[10] B. N.  Sudha, V. G. Sastry, M. S. Harika, N. Yellasubbaiah, Indian J. Chem. Sect. B, 5 (2018) 737.
[11] A. Aminkhani, M. Talati, R. Sharifi, F. Chalabian, F. Katouzian, J. Heterocycl. Chem., 56 (2019) 1812.
[12] A. R. Kiasat, S. Hamid, S. J. Saghanezhad, Nanochem. Res., 1 (2016) 157-165. 
[13]  J. Safaei-Ghomi,  A. Javidan,  A. Ziarati, H. Shahbazi-Alavi,  J. Nanopart. Res., 17 (2015) 338.
[14] P. Nazari, A. Bazi, S. A. Ayatollahi, H. Dolati, S. M. Mahdavi, L. Rafighdoost, M. Amirmostofian, Iran. J. Pharm. Res., 16 (2017) 943.
[15] M. Veverka, Chem. Pap., 46 (1992) 206.
[16] V. A. Ashwood, R. E. Buckingham, F. Cassidy, J. M. Evans, E. A. Faruk, T. C. Hamilton, D. J. Nash, G. Stemp, K. Willcocks, J. Med. Chem., 29 (1986) 2194.
[17] B. C. Pearce, R. A. Parker, M. E. Deason, D. D. Dischino, E. Gillespie, A. A. Qureshi, K. Volk, J. J.
Wright, J. Med. Chem., 37 (1994) 526.
[18] M. M. Ismail, H. S. Rateb, M.M. Hussein, Eur. J. Med. Chem., 45 (2010) 3950.
[19] H. Valizadeh, A. Azimi, J. Iran. Chem. Soc., 8 (2011) 123.
[20] D. Chauhan, S. Hashim, P. Rani, S. Kumar, N. Shrimal, D. Shastri, R. Vinit, Med. Chem., 16 (2020) 1.
[21] M. B. Tehrani, Z. Rezaei, M. Asadi, H. Behnammanesh, H. Nadri, F. Afsharirad, A. Moradi, B.
Larijani, M. Mohammadi-Khanaposhtani, M. Mahdavi, Chem. Biodivers, 16 (2019) e1900144.
[22] R. Soni, S. D. Durgapal, S. S. Soman, J. J. Georrge, Arab. J. Chem., 12 (2019) 701.
[23] S. M. B. H. Ghazvini, P. Safari, A. Mobinikhaledi, H. Moghanian, H. Rasouli, Spectrochim. Acta A Mol. Biomol. Spect., 205 (2018) 111.
[24] V. T. Angelova, P. A. Andreeva-Gateva, N. G. Vassilev, R. Tafradjiiska-Hadjiolova, S. Surcheva, J.
Tchekalarova, Compt. Rend. Acad. Bulg. Sci., 69 (2016) 513.
[25] J. D. Loudon, R. K. Razdan, J. Chem. Soc., (1954) 4299.
[26] W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, C. Crogan-Grundy, D. Labreque, M. Bubenick, G. Attardo, R. Denis, S. Lamothe, H. Gourdeau, B. Tseng, S. Kasibhatla, S. X. Cai, J. Med. Chem., 51 (2008) 417.
[27] W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, Y. Wang, J. Zhao, S. Jia, J. Herich, D. Labreque, R. Storer, K. Meerovitch, D. Bouffard, R. Rej, R. Denis, C. Blais,S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, S. Kasibhatla, S. X. Cai. J. Med. Chem., 47 (2004) 6299.
[28] W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. Gourdeau, B. Tseng, J. Drewe, S. X. Cai, Bioorganic Med. Chem. Lett., 15 (2005) 4745.
[29] M.R. Naimi-Jamal, S. Mashkouri, A. Sharifi, Mol. Diversity, 14 (2010) 473.
[30] B. Sunil Kumar, N. Srinivasulu, R. H. Udupi, B. Rajitha, Y. Thirupathi Reddy, P. Narsimha Reddy, P. S. Kumar, Russ. J. Org. Chem., 42 (2006) 1813.
[31] W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, J. Zhao, C. Crogan-Grundy, L. Xu, S. Lamothe, H.
Gourdeau, R. Denis, B. Tseng, S. Kasibhatla, S. X. Cai. J. Med. Chem., 50 (2007) 2858.
[32] G. Brahmachari, Green Synthetic Approaches for Biologically Relevant Heterocycles, Elsevier, chapter 11, (2015) 185.
[33] K. Gong, H. L. Wang, D. Fang, Z. L. Liu, Catal. Commun., 9 (2008) 650.
[34] B. Baghernejad, M. M. Heravi, H. A. Oskooie, J. Korean Chem. Soc., 53 (2009) 631.
[35] S. Akocak, B. Şen, N. Lolak, A. Şavk, M. Koca, S. Kuzu, F. Şen, Nano-Struct. Nano-Objects, 11 (2017) 25.
[36] R. L. Magar, P. B. Thorat, V. B. Jadhav, S. U. Tekale, S. A. Dake, B. R. Patil, R. P. Pawar, J. Mol.
Catal. A: Chem., 374 (2013) 118-124.
[37] T. Erdmenger,  C. Guerrero-Sanchez,   J. Vitz,  R. Hoogenboom, U. S. Schubert, Chem. Soc. Rev., 39 (2010) 3317.
[38] M.A.E.A.A.  Ali, E. Remaily, S. K. Mohamed, Tetrahedron, 70 (2014) 270.
[39] Y. Abrouki, A. Anouzla, H. Loukili, A. Chakir, M. Idrissi, A. Abrouki, A. Rayadh, M. Zahouily, K. EL. Kacemi, J. Bessiere, B. Marouf, S. Sebti, Am. J. Biol. Chem. Pharm. Sci., 1 (2013) 28.
[40] Y. Peng, G. Song, R. Dou, Green Chem., 8 (2006) 573.
[41] G. Brahmachari, B. Banerjee, ACS Sustainable Chem. Eng., 2 (2013) 411.
[42] A. Arakaki, K. Shimizu,   M. Oda,  T. Sakamoto,  T. Nishimura, T. Kato, Org. Biomol. Chem.,
13 (2015) 974.
[43] A. George, Advances in biomimetics. BoD–Books on Demand, (2011).
[44] S. Weiner, L. Addadi, J. Mater. Chem., 7 (1977) 689.
[45] M. B. Kourandeh, R. Naderloo, N. Khouroshi, S. Zangiabadi, J. Fish. Sci. Technol., 10 (2021) 173.
[46] R.E. Paembonan, F. Ismail, S. Baddu, Najamuddin, I. Tahir, N. Akbar, Inayah, A. Nurhayati, IOP Conf. Ser.: Earth Environ. Sci., 890 (2021) 012055.
[47] Coral Reefs - National Geographic Society (2022). Available at:  https://education.nationalgeographic.org/resource/coral-reefs/.
[48] N. Koga, K. Nishikawa, Cryst. Growth Des., 14 (2014) 879. 
[49] B.  Kaczorowska, A. Hacura, T. Kupka, R. Wrzalik, E. Talik, G. Pasterny, A. Matuszewska, Anal. Bioanal. Chem., 377 (2003) 1032.
[50] H. Li, X. He, Y. Liu, H. Huang, S. Lian, S. T. Lee, Z. Kang, Carbon, 49 (2011) 605.
[51] P. Boudjouk, J. Chem. Educ., 63 (1986) 427.
[52] a) S. Kamwl, T. Hasegawa, S. Yin, T. Takemura, S. Furukawa, M. Matsumoto, Salt and Seawater Science & Technology, 3 (2003) 58. b) R. Febrida, A. Cahyanto, E. Herda, V. Muthukanan, N. Djustiana, F. Faizal, C. Panatarani, I. M. Joni, Materials, 14 (2021) 4425. 
[53] a) N. V. Vagenas, A. Gatsouli, C. G. Kontoyannis, Talanta, 59 (2003) 831. b) Z. Nan, X. Chen, Q. Yang, X. Wang, Z. Shi and W. Hou, J. Colloid Interface Sci., 325 (2008) 331.
[54] S. F. Hojati, A. Amiri, N. Moeini Eghbali, S. Mohamadi, Appl Organometal Chem., (2018) e4235.
[55] M. A. Bodaghifard, A. S. Mobinikhaledi, Appl Organometal Chem., 31 (20177) 2.  
[56] A. Dhakar, R. Goyal, A. Rajput, M. Singh Kaurav, V. S. Tomar, D.D. Agarwala, Curr. Chem. Lett., 8 (2019) 125.
[57] H. Ramadoss, H. Kiyani, S. S. Mansoor, Iran. J. Chem. Chem. Eng., 36 (2017) 19.
[58] M. Fallah-Mehrjardi, M. Shirzadi, S. H. Banitaba, Polycyclic Aromat. Compd., (2020) 1.
[59] A. Moshtaghi Zonouz, I. Eskandari, D. Moghani, Chem. Sci. Trans, 1 (2012) 91.
[60] M. Honarmand, A. Tzani, A. Detsi, J. Mol. Liq., 290 (2019) 111358.  
[61] M. Amirnejad, M. R. Naimi-Jamal, H. Tourani, H. Ghafuri, Monatsh.Chem. Chem. Mon., 144 (2013) 1219.
[62] S. Khaledi, M. Rajabi, A. R. Momeni, H. A. Samimi, J. Albadi, Res. Chem. Intermed., 46
(2020) 3109.
[63] O. Goli-Jolodar, F. Shirini, M. Seddighi, Dyes Pigm., 133 (2016) 292.  
[64] S.E. Zayed, E.I. AbouElmaged, S.A. Metwally, M.H. Elnagdi, Collect. Czech. Chem. Commun., 56
(1991) 2175.
[65] N.S. Babu, N. Pasha, K.T. Venkateswara, P.S. Sai Prasad, N. Lingaiah, Tetrahedron Lett., 49 (2008) 2730.
[66] J. Safaei-Ghomi, R. Teymuri, H. Shahbazi-Alavi, A. Ziarati, Chinese Chemical Letters, 24 (2013) 921.
[67] U.R. Pratap, D.V. Jawale, P.D. Netankar, R.A. Mane, Tetrahedron Lett., 52 (2011) 5817.  
[68] K. Aswin, S.S. Mansoor, K. Logaiya, S.P.N. Sudhan, V.S. Malik, H. Ramadoss, Res. Chem.
Intermed., 40 (2014) 2583. 
[69] J. Safaei-Ghomi, H. Sh, R. Teymuri, Polycyclic Aromatic Compounds, 36 (2016) 1.

  • Receive Date 14 April 2023
  • Revise Date 27 October 2023
  • Accept Date 09 December 2023