پیوندهای مفید
اخبار و اعلانات
آمار
| تعداد نشریات | 41 |
| تعداد شماره‌ها | 1,182 |
| تعداد مقالات | 10,167 |
| تعداد مشاهده مقاله | 19,109,325 |
| تعداد دریافت فایل اصل مقاله | 13,246,316 |
An efficient and one-pot green synthesis of 2-arylsubstituted benzimidazoles catalyzed by nano-Fe3O4@silica sulfuric acid as a recyclable nanomagnetic solid acid catalyst | ||
| Iranian chemical communication | ||
| مقاله 70، دوره 8، شماره 1، فروردین 2020، صفحه 80-91 اصل مقاله (786.29 K) | ||
| نوع مقاله: Original Research Article | ||
| شناسه دیجیتال (DOI): 10.30473/icc.2019.43207.1493 | ||
| نویسندگان | ||
| Mehdi Fallah-Mehrjardi* 1؛ Manizhe Ayazi2؛ Sayed Hossein Banitaba3 | ||
| 1Department of Chemistry, Payame Noor University | ||
| 2Department of Chemistry, Payame Noor University, PB BOX 19395-3697, Tehran, Iran | ||
| 3Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Iran Research Center of Environmental Chemistry, Payame Noor University, Ardakan, Yazd, Iran | ||
| چکیده | ||
| An efficient and green protocol for the synthesis of 2-arylsubstituted benzimidazoles via a condensation reaction of aromatic aldehydes and 1,2-phenylenediamine using nano-Fe3O4@SiO2-SO3H as a solid acid catalyst in ethanol under reflux conditions has been described. The reactions are completed in short times, and the corresponding benzimidazoles are produced with high yields. The present procedure has several advantages, including short reaction times, high yields of products, facile experiment, simple work-up, eco-friendly reaction conditions, and reusability of the catalyst. The catalyst could simply be separated and recovered by an external magnet and reused several times without appreciable loss of catalytic activity. | ||
| کلیدواژه‌ها | ||
| Fe3O4@SiO2-SO3H؛ benzimidazoles؛ 1,2-phenylenediamine؛ aromatic aldehydes؛ green synthesis | ||
| مراجع | ||
|
[1] D. Carcanague, Y.-K. Shue, M.A. Wuonola, M. Uria-Nickelsen, C. Joubran, J.K. Abedi, J. Jones, T.C. Kuehler, J. Med. Chem., 2002, 45, 4300–4309.
[2] M. Lezcano, W. Al-Soufi, M. Novo, E. Rodriguez-Nunez, J.V. Tato, J. Agric. Food. Chem., 2002, 50, 108–112.
[3] A.K. Tewari, A. Mishra, Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 2006, 45, 489–493.
[4] T. Forseca, B. Gigante, T.L. Gilchrist, Tetrahedron, 2001, 57, 1793–1799.
[5] W.A. Denny, G.W. Rewcastle, B.C. Bagley, J. Med. Chem., 1990, 33, 814–819.
[6] I. Tamm, Science, 1954, 120, 847–848.
[7] M.T. Migawa, J.L. Girardet, J.A. Walker, G.W. Koszalka, S.D. Chamberlain, J.C. Drach, L.B. Townsend, J. Med. Chem., 1998, 41, 1242–1251.
[8] A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, L.B. Townsend, J. Med. Chem., 1998, 41, 1252–1262.
[9] T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit, C.J. Michejda, J. Med. Chem., 1997, 40, 4199–4207.
[10] J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, E. Lavioe, J. Med. Chem., 1996, 39, 992–998.
[11] H.M. Elokdah, S.Y. Chai, T.S. Sulkowski, US Patent, 1998, 5 764 473; Chem. Abstr., 1998, 129, 58784g.
[12] Y. Kohara, K. Kubo, E. Imamiya, T. Wada, Y. Inada, T. Naka, J. Med. Chem., 1996, 39, 5228–5235.
[13] H. Zarrinmayeh, D.M. Zimmerman, B.E. Cantrell, D.A. Schober, R.F. Bruns, Bioorg. Med. Chem. Lett., 1999, 9, 647–652.
[14] Y. Bai, J. Lu, Z. Shi, B. Yang, Synlett, 2001, 544–546.
[15] S.I. Alaqeel, J. Saudi Chem. Soc., 2017,21, 229–237.
[16] M.P. Singh, S. Sasmal, W. Lu, M.N. Chatterjee, Synthesis, 2000, 1380–1390.
[17] P.L. Beaulieu, B. Hache, E. Von Moos, Synthesis, 2003, 1683–1692.
[18] R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal. A: Chem., 2004, 214, 155–160.
[19] C. Massimo, E. Francesco, M. Francesca, Synlett, 2004, 1832–1834.
[20] T. Itoh, K. Nagata, H. Ishikawa, A. Ohsawa, Heterocycles, 2004, 63, 2769–2783.
[21] R. Trivedi, S.K. De, R.A. Gibbs, J. Mol. Catal. A: Chem., 2005, 245, 8–11.
[22] P. Gogoi, D. Konwar, Tetrahedron Lett., 2006, 47, 79–82.
[23] H.Q. Ma, Y.L. Wang, J.Y. Wang, Heterocycles, 2006, 68, 1669–1673.
[24] M. Chakrabarty, S. Karmakar, A. Mukherji, S. Arima, Y. Harigaya, Heterocycles, 2006, 68, 967–974.
[25] H. Xiangming, M. Huiqiang, W. Yulu, Arkivoc, 2007, Xiii, 150–154.
[26] R. Kumar Y.C. Joshi, Y.C. E-J. Chem., 2007, 4, 606–610.
[27] C. Mukhopadhyay, P.K. Tapaswi, Tetrahedron Lett., 2008, 49, 6237–6240.
[28] S.K. Dabhade, R.O. Bora, M. Farooqui, C.H. Gill, Chin. Chem. Lett., 2009, 20, 893–897.
[29] G.R. Jadhav, M.U. Shaikh, R.P. Kale, C.H. Gill, Chin. Chem. Lett., 2009, 20, 292–295.
[30] R.S. Joshi, P.G. Mandhane, S.K. Dabhade, C.H. Gill, J. Chin. Chem. Soc., 2010, 57, 1227–1231.
[31] M.A. Chari, D. Shobha, T. Sasaki, Tetrahedron Lett., 2011, 52, 5575–5580.
[32] S. Sajjadifar, S.A. Mirshokraie, N. Javaherneshan, O. Louie, American J. Org. Chem., 2012, 2, 1–6.
[33] B. Sadeghi, M. Ghasemi Nejad, J. Chem., 2013, 1–5.
[34] S.M. Inamdar, V.K. More, S.K. Mandal, Tetrahedron Lett., 2013, 54, 579–583.
[35] A. Teimouria, A.N. Chermahini, H. Salavati, L. Ghorbanian, J. Mol. Catal. A: Chem., 2013, 373, 38–45.
[36] J. Azizian, P. Torabi, J. Noei, Tetrahedron Lett., 2016, 57, 185–188.
[37] C.S. Digwal, U. Yadav, A.P. Sakla, P.V.S. Ramya, S. Aaghaz, A. Kamal, Tetrahedron Lett., 2016, 57, 4012–4016.
[38] H. Ghafuri, E. Esmaili, M. Talebi, C. R. Chimie, 2016, 19, 942–950.
[39] A. Ziarati, A. Sobhani-Nasab, M. Rahimi-Nasrabadi, M.R. Ganjali, A. Badiei, J. Rare Earths, 2017, 35, 374–381.
[40] R. Mohammadi, A. Sajjadi, J. Med. Chem. Sci., 2019, 2, 55–58.
[41] J. Shi, Chem. Rev., 2013, 113, 2139–2181.
[42] P. Nasehi, A. Kiasat, M.K. Mohammadi, Iran. Chem. Commun., 2014, 2, 180–186.
[43] M.M. Heravi, E, Hashemi, F. Azimian, J. Iran. Chem. Soc., 2015, 12, 647–653.
[44] A. Ghorbani‑Choghamarani, M. Hajjami, B. Tahmasbi, N. Noori, J. Iran. Chem. Soc., 2016, 13, 2193–2202.
[45] A. Ghorbani‑Choghamarani, B. Tahmasbi, New J. Chem., 2016, 40, 1205–1212.
[46] A. Mirzaie, J. Med. Chem. Sci., 2018, 1, 5–8.
[47] A.P. Kumar, K. Sudhakara, B.P. Kumar, A. Raghavender, S. Ravi, D.N. Keniec, Y.-I. Lee, Asian J. Nanosci. Mater., 2018, 1, 172–182.
[48] A. Zare, J. Sanjideh, Iran. Chem. Commun., 2018, 6, 416–422.
[49] S. Kamran. A. Amiri Shiri, Chem. Methodol., 2018, 2, 23–38.
[50] S. Gupta, M. Lakshman, J. Med. Chem. Sci., 2019, 2, 51–54.
[51] H. Saeidian, F. Matloubi Moghaddam, A. Pourjavadi, S. Barzegar, R. Soleyman, A. Sohrabi, J. Braz. Chem. Soc., 2009, 20, 466–471.
[52] H. Saeidian, H. Sadighian, M. Arabgari, Z. Mirjafary, S.E. Ayati, E. Najafi, F. M.Moghaddam, Res. Chem. Intermed., 2018, 44, 601–612.
[53] Z. Arzehgara, A. Aydib, M. Mirzaei Heydari, Asian J. Green Chem. 2018, 2, 281–298.
[54] E. Teymoori, A. Davoodnia, A. Khojastehnezhad, N. Hosseininasab, Iran. Chem. Commun., 2019, 7, 271–282.
[55] F. Nemati, M.M. Heravi, R. Saeedi Rad, Chin. J. Catal., 2012, 33, 1825–1831.
[56] H. Naeimi, Z.S. Nazifi, J. Nanopart. Res., 2013, 15, 2026–2036.
[57] A.R. Kiasat, J. Davarpanah, J. Mol. Catal. A: Chem., 2013, 373, 46–54.
[58] J. Safari, Z. Zarnegar, J. Mol. Catal. A: Chem., 2013, 379, 269–276.
[59] A.R. Kiasat, J. Davarpanah, Res. Chem. Intermed., 2015, 41, 2991–3001.
[60] A. Khorshidi, S. Shariati, M. Aboutalebi, N. Mardazad, Iran. Chem. Commun., 2016, 4, 142–145.
[61] B. Dam, A.K. Pal, A. Gupta A. Synth. Commun., 2016, 46, 275–286.
[62] F. Alemi-Tameh, J. Safaei-Ghomi, M. Mahmoudi-Hashemi, R. Teymuri, Res. Chem. Intermed., 2016, 42, 6391–6406.
[63] A. Rostami, A. Ghorbani-Choghamarani, B. Tahmasbi, F. Sharifi, Y. Navasi, D. Moradi, J. Saudi Chem. Soc., 2017, 21, 399–407.
[64] M. Beyki, M. Fallah-Mehrjardi, Iran. Chem. Commun., 2017, 5, 484–493.
[65] J. Safaei-Ghomi, H. Shahbazi-Alavi, Sci. Iran., 2017, 24, 1209–1219.
[66] M. Beyki, M. Fallah-Mehrjardi, Org. Chem. Res., 2017, 3, 103–111.
[67] M. Beyki, M. Fallah-Mehrjardi, Lett. Org. Chem., 2018, 15, 39–44.
[68] M. Fallah-Mehrjardi, Mini-rev. Org. Chem., 2017, 14, 122–129.
[69] N. Ayashi, M. Fallah-Mehrjardi, A.R. Kiasat, Russ. J. Org. Chem., 2017, 53, 846–852.
[70] F. Najafi, M. Fallah-Mehrjardi, Lett. Org. Chem., 2018, 15, 778–786.
[71] H. Talaei, M. Fallah-Mehrjardi, F. Hakimi, J. Chin. Chem. Soc., 2018, 65, 523–530. | ||
|
آمار تعداد مشاهده مقاله: 1,152 تعداد دریافت فایل اصل مقاله: 600 |
||