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Letters in Organic Chemistry

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

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Research Article

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2Hchromen- 3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

Author(s): Abolfazl Olyaei*, Zahra Ghahremany and Mahdieh Sadeghpour

Volume 19, Issue 3, 2022

Published on: 15 June, 2021

Page: [208 - 213] Pages: 6

DOI: 10.2174/1570178618666210615101248

Price: $65

Abstract

A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

Keywords: 4-hydroxycoumarin, ninhydrin, guanidine hydrochloride, chromene, arylamine, solvent-free.

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[1]
Jung, J-C.; Jung, Y-J.; Park, O-S. Synth. Commun., 2001, 31, 1195-1200.
[http://dx.doi.org/10.1081/SCC-100104003]
[2]
Lee, B.H.; Clothier, M.F.; Dutton, F.E.; Conder, G.A.; Johnson, S.S. Bioorg. Med. Chem. Lett., 1998, 8(23), 3317-3320.
[http://dx.doi.org/10.1016/S0960-894X(98)00588-5] [PMID: 9873726]
[3]
Hesse, S.; Kirsch, G. Tetrahedron Lett., 2002, 43, 1213-1215.
[http://dx.doi.org/10.1016/S0040-4039(01)02373-5]
[4]
Adib, M.; Peytam, F.; Rahmanian-Jazi, M.; Mohammadi-Khanaposhtani, M.; Mahernia, S.; Bijanzadeh, H.R.; Jahani, M.; Imanparast, S.; Faramarzi, M.A.; Mahdavi, M.; Larijani, B. New J. Chem., 2018, 42, 17268-17278.
[5]
(a) Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Detsi, A.; Koufaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina, D.J. Eur. J. Med. Chem., 2009, 44(7), 3020-3026.
[http://dx.doi.org/10.1016/j.ejmech.2008.12.027] [PMID: 19232783]
(b) Narendran, K.; Nanthini, R. New J. Chem., 2015, 39, 4948-4956.
[http://dx.doi.org/10.1039/C5NJ00322A]
[6]
Jung, J-C.; Lee, J-H.; Oh, S.; Lee, J-G.; Park, O-S. Bioorg. Med. Chem. Lett., 2004, 14(22), 5527-5531.
[http://dx.doi.org/10.1016/j.bmcl.2004.09.009] [PMID: 15482917]
[7]
Bye, A.; King, H.K.; Biochem, J. 1970, 117(2), 237-245.
[http://dx.doi.org/10.1042/bj1170237] [PMID: 4192639]
[8]
Thaisrivongs, S.; Tomich, P.K.; Watenpaugh, K.D.; Chong, K.T.; Howe, W.J.; Yang, C.P.; Strohbach, J.W.; Turner, S.R.; McGrath, J.P.; Bohanon, M.J.; Lynn, J.; Mulichak, A.; Spinelli, P.; Hinshaw, R.; Pagano, P.; Moon, J.; Ruwart, M.; Wilkinson, K.; Rush, B.; Zipp, G.; Dalga, R.; Schwende, F.; Howard, G.; Padbury, G.; Toth, L.; Zhao, Z.; Koeplinger, K.; Kakuk, T.; Cole, S.; Zaya, R.; Piper, R.; Jeffrey, P. J. Med. Chem., 1994, 37(20), 3200-3204.
[http://dx.doi.org/10.1021/jm00046a002] [PMID: 7932546]
[9]
Bell, R.G.; Caldwell, P.T. Biochemistry, 1973, 12(9), 1759-1762.
[http://dx.doi.org/10.1021/bi00733a015] [PMID: 4699235]
[10]
Hansen, D.B.; Joullie, M.M. Chem. Soc. Rev., 2005, 34(5), 408-417.
[http://dx.doi.org/10.1039/B315496N] [PMID: 15852153]
[11]
Friedman, M. J. Agric. Food Chem., 2004, 52(3), 385-406.
[http://dx.doi.org/10.1021/jf030490p] [PMID: 14759124]
[12]
(a) LaPorte, G.M.; Ramotowski, R.S. J. Forensic Sci., 2003, 48(3), 658-663.
[http://dx.doi.org/10.1520/JFS2002342] [PMID: 12762543]
(b) Schwarz, L.; Frerichs, I. J. Forensic Sci., 2002, 47(6), 1274-1277.
[http://dx.doi.org/10.1520/JFS15559J] [PMID: 12455648]
(c) Nagaraja, P. Anal. Sci., 2002, 18, 1027-1030.
[http://dx.doi.org/10.2116/analsci.18.1027] [PMID: 12243398]
(d) Pavia, M.; Trujillo, A.J.; Guamis, B.; Ferragut, V. J. Dairy Sci., 2000, 83(7), 1441-1447.
[http://dx.doi.org/10.3168/jds.S0022-0302(00)75014-4] [PMID: 10908050]
(e) Moulin, M.; Deleu, C.; Larher, F.R.; Bouchereau, A. Anal. Biochem., 2002, 308(2), 320-327.
[http://dx.doi.org/10.1016/S0003-2697(02)00202-6] [PMID: 12419346]
[13]
(a) Khalil, A.M.; Berghot, M.A.; Gouda, M.A. Eur. J. Med. Chem., 2009, 44(11), 4434-4440.
[http://dx.doi.org/10.1016/j.ejmech.2009.06.002] [PMID: 19581025]
(b) Catto, M.; Aliano, R.; Carotti, A.; Cellamare, S.; Palluotto, F.; Purgatorio, R.; De Stradis, A.; Campagna, F. Eur. J. Med. Chem., 2010, 45(4), 1359-1366.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.029] [PMID: 20137834]
(c) Prabhakar, K.R.; Veerapur, V.P.; Bansal, P.; Vipan, K.P.; Reddy, K.M.; Barik, A.; Reddy, B.K.D.; Reddanna, P.; Priyadarsini, K.I.; Unnikrishnan, M.K. Bioorg. Med. Chem., 2006, 14(21), 7113-7120.
[http://dx.doi.org/10.1016/j.bmc.2006.06.068] [PMID: 16889968]
(d) Ghalib, R.M.; Hashim, R.; Mehdi, S.H.; Sulaiman, O.; Silva, P.S.P.; Jassbi, A.R.; Firuzi, O.; Kawamura, F.; Chan, K-L.; Murugaiyah, V. Lett. Org. Chem., 2012, 9, 767-774.
[14]
(a) Mohammadi Ziarani, G.; Lashgari, N.; Azimian, F.; Kruger, H.G.; Gholamzadeh, P. ARKIVOC, 2015, (vi), 1-139.
(b) Dus, S. RSC Advances, 2020, 10, 18875-18906.
[http://dx.doi.org/10.1039/D0RA02930K]
(c) Liu, T.; Lai, Y-H.; Yu, Y-Q.; Xu, D-Z. New J. Chem., 2018, 42, 1046-1051.
[http://dx.doi.org/10.1039/C7NJ03967K]
(d) Maharani, S.; Kumar, S.V.; Almansour, A.I.; Kumar, R.S.; Kandasamy, A.; Kumar, R.R. New J. Chem., 2017, 41, 11009-11015.
[http://dx.doi.org/10.1039/C7NJ01673E]
[15]
Sangshetti, J.N.; Khan, F.A.K.; Kute, C.S.; Zaheer, Z.; Ahmed, R.Z. Russ. J. Org. Chem., 2015, 51, 69-73.
[http://dx.doi.org/10.1134/S107042801501011X]
[16]
Ghafuri, H.; Ghorbani, B.; Rashidizadeh, A.; Talebi, M.; Roshani, M. Appl. Organomet. Chem., 2017, 32, 4147-4152.
[http://dx.doi.org/10.1002/aoc.4147]
[17]
Dehghan, A.; Shams, N. Life Sci., 2015, 5, 5288-5293.
[18]
Kumar, A.; Gupta, M.K.; Kumar, M. Tetrahedron Lett., 2001, 52, 4521-4523.
[http://dx.doi.org/10.1016/j.tetlet.2011.06.040]
[19]
Zahiri, S.; Mokhtary, M.J. Taibah. Univ. Med. Sci., 2015, 9, 89-94.
[http://dx.doi.org/10.1016/j.jtusci.2014.09.006]
[20]
Rao, P.; Konda, S.; Iqubal, J.; Oruganti, S. Tetrahedron Lett., 2012, 53, 5314-5317.
[http://dx.doi.org/10.1016/j.tetlet.2012.07.098]
[21]
Zaheer, Z.; Kalam, F.A. Chin. Chem. Lett., 2016, 27, 287-294.
[http://dx.doi.org/10.1016/j.cclet.2015.10.028]
[22]
Anaraki-Ardakani, H.; Zaki, E. Ind. J. Fundamental App. Life Sci., 2015, 5, 5421-5427.
[23]
Ghashang, M.; Shafiee, M.R.M.; Delzendeh, S.; Fazlinia, A.; Esfandiari, H.; Biregan, M.N.; Heydari, N. Bulg. Chem. Commun.,, 2016, 48, 694-697.
[24]
Ghosh, P.P.; Das, A.R. Tetrahedron Lett., 2012, 53, 3140-3143.
[http://dx.doi.org/10.1016/j.tetlet.2012.04.033]
[25]
Olyaei, A.; Dortaj, E.; Khoeiniha, R.; Rajabi, F. J. Heterocycl. Chem., 2018, 55, 2971-2976.
[http://dx.doi.org/10.1002/jhet.3379]
[26]
(a) Olyaei, A.; Javarsineh, S.; Sadeghpour, M. Chem. Heterocycl. Compd., 2018, 54, 934-939.
[http://dx.doi.org/10.1007/s10593-018-2376-x]
(b) Olyaei, A.; Abforushha, E.S.; Khoeiniha, R. Lett. Org. Chem., 2017, 14, 103-108.
[http://dx.doi.org/10.2174/1570178614666170201171426]
(c) Olyaei, A.; Zarnegar, M.; Sadeghpour, M.; Rezaei, M. Lett. Org. Chem., 2012, 9, 451-456.
[http://dx.doi.org/10.2174/157017812801322499]
(d) Noruzian, F.; Olyaei, A.; Hajinasiri, R. Res. Chem. Intermed., 2019, 45, 4383-4394.
[http://dx.doi.org/10.1007/s11164-019-03837-w]
(e) Noruzian, F.; Olyaei, A.; Hajinasiri, R.; Sadeghpour, M. Synth. Commun., 2019, 49, 2717-2724.
[http://dx.doi.org/10.1080/00397911.2019.1643483]
(f) Olyaei, A.; Mohammad Ebrahimi, R.; Adl, A.R.; Sadeghpour, M. Chem. Heterocycl. Compd., 2019, 55, 1104-1110.
[http://dx.doi.org/10.1007/s10593-019-02585-4]
(g) Olyaei, A.; Rezaei, M. Lett. Org. Chem., 2013, 10, 311-316.
[http://dx.doi.org/10.2174/1570178611310050002]
(h) Sadeghpour, M.; Mohammadgoliha, M. Lett. Org. Chem., 2017, 14, 128-133.
[http://dx.doi.org/10.2174/1570178614666170207141938]

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