Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

An Efficient and Green Procedure for the Synthesis of Quinoxaline Derivatives using 3,5-Bis(trifluoromethyl)phenylammonium triflate (BFPAT) Organocatalyst

Author(s): Mandana Alipour, Zinatossadat Hossaini, Samad Khaksar* and Faramarz Rostami-Charati

Volume 18, Issue 3, 2021

Published on: 13 March, 2020

Page: [183 - 186] Pages: 4

DOI: 10.2174/1570178617666200313105049

Price: $65

Abstract

The application of 3,5-bis(trifluoromethyl)phenylammonium triflate (BFPAT) as a convenient new organocatalyst for the synthesis of quinoxaline derivatives is described. In the presence of BFPAT, one-pot synthesis of a wide variety of quinoxaline derivatives was achieved by the reaction of various o-phenylenediamines and 1,2-dicarbonyl compounds in water.

Keywords: Cavitands, green chemistry, heterocyclics, kinase inhibitors, organocatalyst, quinoxalines.

Graphical Abstract
[1]
MacMillan, D.W.C. Nature, 2008, 455(7211), 304-308.
[http://dx.doi.org/10.1038/nature07367] [PMID: 18800128]
[2]
Seayad, J.; List, B. Org. Biomol. Chem., 2005, 3(5), 719-724.
[http://dx.doi.org/10.1039/b415217b] [PMID: 15731852]
[3]
Schreiner, P.R. Chem. Soc. Rev., 2003, 32(5), 289-296.
[http://dx.doi.org/10.1039/b107298f] [PMID: 14518182]
[4]
Dalko, P.I.; Moisan, L. Angew. Chem. Int. Ed., 2004, 43, 5138-5175.
[http://dx.doi.org/10.1002/anie.200400650]
[5]
Renzi, P.; Bella, M. Chem. Commun. (Camb.), 2012, 48(55), 6881-6896.
[http://dx.doi.org/10.1039/c2cc31599h] [PMID: 22662324]
[6]
Li, J.; Lin, S.; Dai, J.; Su, W. J. Chem. Res., 2010, 34, 196-199.
[http://dx.doi.org/10.3184/030823410X12698803608765]
[7]
Wakasugi, K.; Misaki, T.; Yamada, K.; Tanabe, Y. Tetrahedron Lett., 2000, 41, 5249-5252.
[http://dx.doi.org/10.1016/S0040-4039(00)00821-2]
[8]
Funatomi, T.; Wakasugi, K.; Misaki, T.; Tanabe, Y. Green Chem., 2006, 8, 1022-1027.
[http://dx.doi.org/10.1039/b609181b]
[9]
Shen, Z.L.; Jiang, X.Z. J. Mol. Catal. Chem., 2004, 213, 193-198.
[http://dx.doi.org/10.1016/j.molcata.2003.12.008]
[10]
Mercs, L.; Pozzi, G.; Quici, S. Tetrahedron Lett., 2007, 48, 3053-3056.
[http://dx.doi.org/10.1016/j.tetlet.2007.02.117]
[11]
Li, J.; He, P.; Yu, C. Tetrahedron, 2012, 68, 4138-4144.
[http://dx.doi.org/10.1016/j.tet.2012.03.104]
[12]
Iida, A.; Osada, J.; Nagase, R.; Misaki, T.; Tanabe, Y. Org. Lett., 2007, 9(10), 1859-1862.
[http://dx.doi.org/10.1021/ol070191b] [PMID: 17429977]
[13]
Khaksar, S.; Ostad, S.M. J. Fluor. Chem., 2011, 132, 937-939.
[http://dx.doi.org/10.1016/j.jfluchem.2011.07.011]
[14]
He, W.; Myers, M.R.; Hanney, B.; Spada, A.P.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, M.H. Bioorg. Med. Chem. Lett., 2003, 13(18), 3097-3100.
[http://dx.doi.org/10.1016/S0960-894X(03)00655-3 ] [PMID: 12941342]
[15]
Thomas, K.R.J.; Velusamy, M.; Lin, J.T.; Chuen, C-H.; Tao, Y-T. Chem. Mater., 2005, 17, 1860-1866.
[http://dx.doi.org/10.1021/cm047705a]
[16]
Dailey, S.; Feast, W.J.; Peace, R.J.; Sage, I.C.; Till, S.; Wood, E.L. J. Mater. Chem., 2001, 11, 2238-2243.
[http://dx.doi.org/10.1039/b104674h]
[17]
Hegedus, L.S.; Greenberg, M.M.; Wendling, J.J.; Bullock, J.P. J. Org. Chem., 2003, 68(11), 4179-4188.
[http://dx.doi.org/10.1021/jo020708r] [PMID: 12762716]
[18]
Sessler, J.L.; Maeda, H.; Mizuno, T.; Lynch, V.M.; Furuta, H. J. Am. Chem. Soc., 2002, 124(45), 13474-13479.
[http://dx.doi.org/10.1021/ja0273750] [PMID: 12418900]
[19]
Ott, S.; Faust, R. Synlett, 2004, 1509-1512.
[20]
Crossley, M.J.; Johnston, L.A. Chem. Commun. (Camb.), 2002, (10), 1122-1123.
[http://dx.doi.org/10.1039/b111655j] [PMID: 12122695]
[21]
Hirayama, T.; Yamasaki, S.; Ameku, H.; Ishi-i, T.; Thiemann, T.; Mataka, S. Dyes Pigments, 2005, 67, 105-110.
[http://dx.doi.org/10.1016/j.dyepig.2004.09.023]
[22]
Seitz, L.E.; Suling, W.J.; Reynolds, R.C. J. Med. Chem., 2002, 45(25), 5604-5606.
[http://dx.doi.org/10.1021/jm020310n] [PMID: 12459027]
[23]
Brown, D.J. The Chemistry of Heterocyclic Compounds. Quinoxalines. Supplement II; John Wiley & Sons, Inc.: Hoboken, New Jersey, USA, 2004.
[24]
Zhao, Z.; Wisnoski, D.D.; Wolkenberg, S.E.; Leister, W.H.; Wang, Y.; Lindsley, C.W. Tetrahedron Lett., 2004, 45, 4873-4876.
[http://dx.doi.org/10.1016/j.tetlet.2004.04.144]
[25]
Mirjalili, B.B.F.; Bamoniri, A.; Akbari, A. Iran. J. Catal., 2011, 1, 87-92.
[26]
Kaupp, G.; Naimi‐Jamal, M.R. Eur. J. Org. Chem., 2002, 1368-1373.
[http://dx.doi.org/10.1002/1099-0690(200204)2002:8<1368:AID-EJOC1368>3.0.CO;2-6]
[27]
Darabi, H.R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. Catal. Commun., 2007, 8, 389-392.
[http://dx.doi.org/10.1016/j.catcom.2006.06.033]
[28]
Heravi, M.M.; Taheri, S.; Bakhtiari, K.; Oskooie, H.A. Catal. Commun., 2007, 8, 211-214.
[http://dx.doi.org/10.1016/j.catcom.2006.06.013]
[29]
Li, Z.; Li, W.; Sun, Y.; Huang, H.; Ouyang, P. J. Heterocycl. Chem., 2008, 45, 285-288.
[http://dx.doi.org/10.1002/jhet.5570450135]
[30]
Srinivas, C.; Kumar, C.N.S.S.P.; Rao, V.J.; Palaniappan, S. J. Mol. Catal. Chem., 2007, 265, 227-230.
[http://dx.doi.org/10.1016/j.molcata.2006.10.018]
[31]
Sithambaram, S.; Ding, Y.; Li, W.; Shen, X.; Gaenzler, F.; Suib, S.L. Green Chem., 2008, 10, 1029-1032.
[http://dx.doi.org/10.1039/b805155k]
[32]
Cai, J-J.; Zou, J-P.; Pan, X-Q.; Zhang, W. Tetrahedron Lett., 2008, 49, 7386-7390.
[http://dx.doi.org/10.1016/j.tetlet.2008.10.058]
[33]
Huang, T-k.; Wang, R.; Shi, L.; Lu, X-x. Catal. Commun., 2008, 9, 1143-1147.
[http://dx.doi.org/10.1016/j.catcom.2007.10.024]
[34]
Liu, J-Y.; Liu, J.; Wang, J-D.; Jiao, D-Q.; Liu, H-W. Synth. Commun., 2010, 40, 2047-2056.
[http://dx.doi.org/10.1080/00397910903219401]
[35]
Ajaikumar, S.; Pandurangan, A. Appl. Catal. A Gen., 2009, 357, 184-192.
[http://dx.doi.org/10.1016/j.apcata.2009.01.021]
[36]
Niknam, K.; Saberi, D.; Mohagheghnejad, M. Molecules, 2009, 14(5), 1915-1926.
[http://dx.doi.org/10.3390/molecules14051915] [PMID: 19471211]
[37]
Darabi, H.R.; Aghapoor, K.; Mohsenzadeh, F.; Taala, F.; Asadollahnejad, N.; Badiei, A. Catal. Lett., 2009, 133, 84-89.
[http://dx.doi.org/10.1007/s10562-009-0161-2]
[38]
Heravi, M.M.; Tehrani, M.H.; Bakhtiari, K.; Oskooie, H.A. Catal. Commun., 2007, 8, 1341-1344.
[http://dx.doi.org/10.1016/j.catcom.2006.11.026]
[39]
Khaksar, S.; Rostamnezhad, F. Bull. Korean Chem. Soc., 2012, 33, 2581-2584.
[http://dx.doi.org/10.5012/bkcs.2012.33.8.2581]
[40]
Narsaiah, A.V.; Kumar, J.K. Synth. Commun., 2012, 42, 883-892.
[http://dx.doi.org/10.1080/00397911.2010.533050]
[41]
Oskooie, H.A.; Heravi, M.M.; Bakhtiari, K.; Taheri, S. Monatsh. Chem., 2007, 138, 875-877.
[http://dx.doi.org/10.1007/s00706-007-0694-2]
[42]
Zi, J.; Gu, D-W.; Zhang, Y.; Hu, Z-Y.; Zhang, X-Q.; Guo, X-X. Synth. Commun., 2018, 48, 915-920.
[http://dx.doi.org/10.1080/00397911.2018.1428752]
[43]
Khan, K.M.; Hussain, S.; Perveen, S.; Rahim, F.; Yousuf, S.; Hussain, E. Lett. Org. Chem., 2014, 11, 426-431.
[http://dx.doi.org/10.2174/1570178611666140304000936]
[44]
Lü, H.Y.; Yang, S-H.; Deng, J.; Zhang, Z-H. Aust. J. Chem., 2010, 63, 1290-1296.
[http://dx.doi.org/10.1071/CH09532]
[45]
J.T.J. Heterocycl, Chem, 2010, 47, 703-706.
[46]
Indalkar, K.S.; Khatri, C.K.; Chaturbhuj, G.U. J. Chem. Sci., 2017, 129, 141-148.
[http://dx.doi.org/10.1007/s12039-017-1235-0]
[47]
Abadi, S.S.A.D.M.; Abdollahi-Alibeik, M. Silicon, 2018, 10, 1667-1678.
[http://dx.doi.org/10.1007/s12633-017-9651-9]
[48]
Abdelraheem, E.M.M.; Khaksar, S.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Shaabani, S.; Dömling, A. J. Org. Chem., 2018, 83(3), 1441-1447.
[http://dx.doi.org/10.1021/acs.joc.7b02984] [PMID: 29327924]
[49]
Khaksar, S.; Gholami, M. Res. Chem. Intermed., 2015, 41, 3709-3718.
[http://dx.doi.org/10.1007/s11164-013-1483-7]
[50]
Khaksar, S.; Behzadi, N. Chin. J. Catal., 2012, 33, 982-985.
[http://dx.doi.org/10.1016/S1872-2067(11)60393-8]
[51]
Khaksar, S.; Tajbakhsh, M.; Gholami, M.; Rostamnezhad, F. Chin. Chem. Lett., 2014, 25, 1287-1290.
[http://dx.doi.org/10.1016/j.cclet.2014.04.008]
[52]
Khaksar, S.; Vahdat, S.M.; Moghaddamnejad, R.N. Monatsh. Chem., 2012, 143, 1671-1674.
[http://dx.doi.org/10.1007/s00706-012-0752-2]
[53]
Khaksar, S.; Behzadi, N. Comb. Chem. High T. Scr., 2012, 15, 845-848.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy