پیوندهای مفید
اخبار و اعلانات
آمار
| تعداد نشریات | 41 |
| تعداد شماره‌ها | 1,112 |
| تعداد مقالات | 9,521 |
| تعداد مشاهده مقاله | 17,163,582 |
| تعداد دریافت فایل اصل مقاله | 12,018,706 |
N1,N1,N2,N2-Tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride as a highly efficient catalyst for synthesis of some nitrogen- and oxygen-containing heterocyclic compounds | ||
| Iranian chemical communication | ||
| مقاله 1، دوره 7، Issue 3, pp. 160-229, Serial No. 24، مهر 2019، صفحه 160-173 اصل مقاله (743.75 K) | ||
| نوع مقاله: Original Research Article | ||
| شناسه دیجیتال (DOI): 10.30473/icc.2018.40557.1441 | ||
| نویسندگان | ||
| Maryam Dashtizadeh1؛ Maryam Khalili1؛ Fatemeh Reghbat1؛ Eshagh Abdi1؛ Zahra Bahadori1؛ Zahra Sadripour1؛ Abdolkarim Zare* 2؛ Khadijeh Didehban1؛ Seyed Sajad Sajadikhah3 | ||
| 1Department of Chemistry, Payame Noor University, P.O. Box 19395-4697 Tehran, Iran | ||
| 2Department of Chemistry, Payame Noor University of Bushehr, Bushehr, Iran | ||
| 3Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran | ||
| چکیده | ||
| In this research, a Brønsted acidic ionic liquid namely N1,N1,N2,N2-tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride {[TMBSED][Cl]2} was employed as a highly efficient catalyst for the solvent-free production of some nitrogen- and oxygen-containing heterocyclic compounds including: (i) polyhydroquinolines (from arylaldehydes, dimedone, β-ketoesters and ammonium acetate), (ii) 3,4-dihydropyrimidin-2-(1H)-ones/thiones (from arylaldehydes, β-ketoesters and urea/thiourea), and (iii) 14-aryl-14H-dibenzo[a,j]xanthenes (from aromatic aldehydes and β-naphthol). In all cases, the heterocycles were obtained in high yields and in short reaction times. The salient features of using [TMBSED][Cl]2 in the reactions, include effectiveness, generality, simple preparation of the catalyst from inexpensive and easy available reactants, achieving the reactions under solvent-free conditions, synthesis of the products with high yields in short reaction times and need to milder conditions compared with many reported methods for the preparation of the aforesaid organic compounds. | ||
| کلیدواژه‌ها | ||
| [TMBSED][Cl]2؛ polyhydroquinoline؛ dihydropyrimidin-2-(1H)-one؛ 3,4-dihydropyrimidin-2-(1H)-thione؛ 14-aryl-14H-dibenzoxanthene | ||
| مراجع | ||
|
[1] A.S. BronycaClare, D.R. MacFarlane, Ionic Liquids (Topics in Current Chemistry), Kirchner, B. (Ed.), Springer, 2010.
[2] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H.G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem., 2012, 77, 3640-3645.
[3] A. Zare, M. Rezaei, A. Hasaninejad, Iran. Chem. Commun.,2016, 4, 94-101.
[4] S. Rezayati, R. Hajinasiri, Z. Hossaini, S. Abbaspour, Asian J. Green Chem., 2018, 2, 268-280.
[5] A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal., 2017, 7, 233-241.
[7] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A Gen.,2011, 400, 70-81.
[8] S. Keskin, D. Kayrak-Talay, U. Akman, Ö. Hortaçsu, J. Supercrit. Fluids, 2007, 43, 150-180.
[9] S. Sowmiah, V. Srinivasadesikan, M.-C. Tseng, Y.-H. Chu, Molecules, 2009, 14, 3780-3813.
[10] A. Kumar, R.A. Maurya, Tetrahedron Lett., 2007, 48, 3887-3890.
[11] S.J. Garden, C.R.W. Guimaraes, M.B. Correa, C.A.F.D. Oleveira, A.D.C. Pinto, R.B.D. Alencastro, J. Org. Chem., 2003, 68, 8815-8822.
[12] A. Heydari, S. Khaksar, M. Tajbakhsh, H.R. Bijanzadeh, J. Fluor. Chem., 2009, 130, 609-614.
[13] R.H. Boecker, F. P. Guengerich, J. Med. Chem., 1986, 29, 1596-1603.
[14] V. Klusa, Drugs Future, 1995, 20, 135-138.
[15] R.G. Bretzel, C.C. Bollen, E. Maeser, K.F. Federlin, Drugs Future, 1992, 17, 465-468.
[16] M. Nasr-Esfahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, H. Nasrabadi, J. Mol. Catal. A: Chem., 2014, 382, 99-105.
[17] F. Matloubi Moghaddam, H. Saeidian, Z. Mirjafary, A. Sadeghi, J. Iran. Chem. Soc., 2009, 6, 317-324. [18] A.S. Somwanshia, V.U. Panditb, A.D. Gholapa, R.D. Ghogarea, S.S. Pandit, Iran. Chem. Commun., 2017, 5, 293-300.
[19] A. Kumar, R.A. Maurya, Tetrahedron, 2007, 63, 1946-1952.
[20] J.S. Yoo, T.J. Laughlin, J.J. Krob, R.S. Mohan, Tetrahedron Lett., 2015, 56, 4060-4062.
[21] Z., Zarnegar, J. Safari, Z. Mansouri-Kafroudi, Catal. Commun., 2015, 59, 216-221.
[22] A. Zare, F. Abi, A.R. Moosavi-Zare, M.H. Beyzavi, M.A., Zolfigol, J. Mol. Liq., 2013, 178, 113-121.
[23] M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, J. Magn. Magn. Mater., 2016, 398, 205-214.
[24] G. Mohammadi Ziarani, A.R. Badiei, Y. Khaniania, M. Haddadpour, Iran. J. Chem. Chem. Eng., 2010, 29, 1-10.
[25] Z.D. Aron, L.E. Overman, Chem. Commun., 2004, 253-265.
[26] S.J. Haggarty, T.U. Mayer, D.T. Miyamoto, R. Fathi, R.W. King, T.J. Mitchison, S.L. Schreiber, Chem. Biol., 2000, 7, 275-286.
[27] M. Yarim, S. Sarac, F.S. Kilic, K. Erol, IL Farmaco, 2003, 58, 17-24.
[28] C.O. Kappe, Eur. J. Med. Chem., 2000, 35, 1043-1052.
[29] M.Z. Kassaee, H. Masrouri, F. Movahedi, R. Mohammadi, Helv. Chim. Acta, 2010, 93, 261-264.
[30] M. Moghaddasi, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, Chin. J. Catal., 2012, 33, 706-710.
[31] A. Ghorbani-Choghamarani, P. Zamani, Chin. Chem. Lett., 2013, 24, 804-808.
[32] A.R. Momeni, H.A. Samimi, H. Vaezzadeh, Chem. Method., 2018, 2, 260-269.
[33] F. Tamaddon, S. Ghazi, Catal. Commun., 2015, 72, 63-67.
[34] R. Tayebee, M.M. Amini, M. Ghadamgahi, M. Armaghan, J. Mol. Catal. A Chem., 2013, 366, 266-274.
[35] H. Eshghi, A. Javid, A. Khojastehnezhad, F. Moeinpour, F.F. Bamoharram, M. Bakavoli, M. Mirzaei, Chin. J. Catal., 2015, 36, 299-307.
[36] A. Zare, Z. Nasouri, J. Mol. Liq., 2016, 216, 364-369.
[37] M. Kargar, R. Hekmatshoar, A. Mostashari, Z. Hashemi, Catal. Commun., 2011, 15, 123-126.
[38] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, G. Narcisse, G. Uchida-Ernouf, R. Lacroix, Eur. J. Med. Chem., 1978, 13, 67-71.
[39] J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Cell. Biol. Int. Rep., 1990, 14, 1075-1084.
[40] T. Hideo, Jpn. Tokkyo Koho JP 56005480, 1981; Chem. Abstr., 1981, 95, 80922b. [41] S.M. Menchen, S.C. Benson, J.Y.L. Lam, W. Zhen, D. Sun, B.B. Rosenblum, S.H. Khan, M., Taing, U.S. Patent 6, 583, 168, 2003.
[42] C.G. Knight, V. Stephens, Biochem. J., 1989, 258, 683-687.
[43] M. Hong, C. Cai, J. Fluorine Chem., 2009, 130, 989-992.
[44] F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc., 2011, 8, S129-S134.
[45] Z. Arzehgar, A. Aydi, M. Mirzaei Heydari, Asian J. Green Chem., 2018, 2, 281-298.
[46] A. Zare, S. Ahmadi, F. Abi, T. Hekmat-Zadeh, M. Merajoddin, M. Hatami, M. Keshtkar, A. Khazaei, Sci. Iran. C, 2015, 22, 2271-2281.
[47] A. Zare, M. Merajoddin, F. Abi, A.R. Moosavi-Zare, M. Mokhlesi, M.A. Zolfigol, Z. Asgari, V. Khakyzadeh, A. Hasaninejad, A. Khalafi-Nezhad, A. Parhami, J. Chin. Chem. Soc.,2012, 59, 860-865.
[48] H. Naeimi, Z.S. Nazifi, C. R. Chim., 2014, 17, 41-48.
[49] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, M.A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M.H. Beyzavi, E. Rostami, A. Argoon, R. Roohandeh, J. Mol. Liq., 2012, 167, 69-77. [50] A.R. Moosavi-Zare, M.A. Zolfigol, O. Khaledian, V. Khakyzadeh, Chin. J. Catal.,2014, 35, 573-578. [51] F. Heidarizadeh, M.M. Zahedi, S. Nourizad, Sci. Iran. C, 2015, 22, 919-924. | ||
|
آمار تعداد مشاهده مقاله: 804 تعداد دریافت فایل اصل مقاله: 458 |
||