Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

A Green and Convenient Approach for the Synthesis of Indole-acrylonitrile and Indole-coumarin Hybrids in Aqueous Media

Author(s): Adeleh Moshtaghi Zonouz* and Davoud Moghani

Volume 21, Issue 5, 2024

Published on: 22 January, 2024

Page: [448 - 455] Pages: 8

DOI: 10.2174/0115701786275818231117053307

Price: $65

conference banner
Abstract

Indole–acrylonitrile hybrids were synthesized via a catalyst-free reaction of aromatic aldehydes and 3-(cyanoacetyl)indole in aqueous media. Also, indole-coumarin hybrids were synthesized via a domino reaction of salicylaldehyde derivatives and 3-(cyanoacetyl)indole in the presence of ammonium acetate in aqueous media. The advantages of the present protocol are high yields, short reaction times, mild reaction conditions, operational simplicity, and environmentally benign, and also there is no need to purification of products.

Keywords: Indole–acrylonitrile hybrids, indole-coumarin hybrids, aqueous media, domino reaction, anti-inflammatory, organic solvents.

Graphical Abstract
[1]
Houlihan, W.J.; Remers, W.A.; Brown, R.K. Indoles; Wiley: New York, 1992.
[2]
Sundberg, R.J. The Chemistry of Indoles; Academic Press: New York, 1996.
[3]
Sravanthi, T.V.; Manju, S.L. Eur. J. Pharm. Sci., 2016, 91, 1-10.
[http://dx.doi.org/10.1016/j.ejps.2016.05.025] [PMID: 27237590]
[4]
Chadha, N.; Silakari, O. Eur. J. Med. Chem., 2017, 134, 159-184.
[http://dx.doi.org/10.1016/j.ejmech.2017.04.003] [PMID: 28412530]
[5]
Kumar, D.; Sharma, S.; Kalra, S.; Singh, G.; Monga, V.; Kumar, B. Curr. Drug Targets, 2020, 21(9), 864-891.
[http://dx.doi.org/10.2174/18735592MTA1FMTE62] [PMID: 32156235]
[6]
Kumar, R.; Lee, M.H.; Mickael, C.; Kassa, B.; Pasha, Q.; Tuder, R.; Graham, B. ERJ Open Res., 2020, 6(4), 00405-02020.
[http://dx.doi.org/10.1183/23120541.00405-2020] [PMID: 33313306]
[7]
Kumari, A.; Singh, R.K. Bioorg. Chem., 2019, 89, 103021.
[http://dx.doi.org/10.1016/j.bioorg.2019.103021] [PMID: 31176854]
[8]
Yadav, J.S.; Reddy, B.V.S.; Narasimhulu, G.; Reddy, N.S.; Reddy, P.N.; Purnima, K.V.; Naresh, P.; Jagadeesh, B. Tetrahedron Lett., 2010, 51(2), 244-247.
[http://dx.doi.org/10.1016/j.tetlet.2009.10.128]
[9]
Kumar, D.; Sundaree, S.; Johnson, E.O.; Shah, K. Bioorg. Med. Chem. Lett., 2009, 19(15), 4492-4494.
[http://dx.doi.org/10.1016/j.bmcl.2009.03.172] [PMID: 19559607]
[10]
Radwan, M.A.A.; Ragab, E.A.; Sabry, N.M.; El-Shenawy, S.M. Bioorg. Med. Chem., 2007, 15(11), 3832-3841.
[http://dx.doi.org/10.1016/j.bmc.2007.03.024] [PMID: 17395469]
[11]
Rapolu, S.; Alla, M.; Bommena, V.R.; Murthy, R.; Jain, N.; Bommareddy, V.R.; Bommineni, M.R. Eur. J. Med. Chem., 2013, 66, 91-100.
[http://dx.doi.org/10.1016/j.ejmech.2013.05.024] [PMID: 23792319]
[12]
Dadashpour, S.; Emami, S. Eur. J. Med. Chem., 2018, 150, 9-29.
[http://dx.doi.org/10.1016/j.ejmech.2018.02.065] [PMID: 29505935]
[13]
Wan, Y.; Li, Y.; Yan, C.; Yan, M.; Tang, Z. Eur. J. Med. Chem., 2019, 183, 111691.
[http://dx.doi.org/10.1016/j.ejmech.2019.111691] [PMID: 31536895]
[14]
Yuan, W.; Yu, Z.; Song, W.; Li, Y.; Fang, Z.; Zhu, B.; Li, X.; Wang, H.; Hong, W.; Sun, N. Infect. Drug Resist., 2019, 12, 2283-2296.
[http://dx.doi.org/10.2147/IDR.S208757] [PMID: 31413605]
[15]
Qin, H.L.; Liu, J.; Fang, W.Y.; Ravindar, L.; Rakesh, K.P. Eur. J. Med. Chem., 2020, 194, 112245.
[http://dx.doi.org/10.1016/j.ejmech.2020.112245] [PMID: 32220687]
[16]
Mazzotta, S.; Frattaruolo, L.; Brindisi, M.; Ulivieri, C.; Vanni, F.; Brizzi, A.; Carullo, G.; Cappello, A.R.; Aiello, F. Future Med. Chem., 2020, 12(1), 5-17.
[http://dx.doi.org/10.4155/fmc-2019-0234] [PMID: 31710253]
[17]
Dorababu, A. Med. Chem., 2020, 11, 1335.
[18]
Nieto, M.J.; Lupton, H.K. Curr. Med. Chem., 2021, 28(24), 4828-4844.
[http://dx.doi.org/10.2174/0929867327666201102114923] [PMID: 33138747]
[19]
Jasiewicz, B.; Okupnik, W.K.; Przygodzki, M.; Warz˙ajtis, B.; Rychlewska, U.; Pospieszny, T. Sci. Rep., 2021, 11, 15425.
[http://dx.doi.org/10.1038/s41598-021-94904-z] [PMID: 34326403]
[20]
Reddy, G.S.; Pal, M. Curr. Med. Chem., 2021, 28(22), 4531-4568.
[http://dx.doi.org/10.2174/1875533XMTEwcMDkow] [PMID: 32951569]
[21]
Zhu, Y.; Zhao, J.; Luo, L.; Gao, Y.; Bao, H.; Li, P.; Zhang, H. Eur. J. Med. Chem., 2021, 223, 113665.
[http://dx.doi.org/10.1016/j.ejmech.2021.113665] [PMID: 34192642]
[22]
Mehra, A. ChemistrySelect, 2022, 7, e202202361.
[http://dx.doi.org/10.1002/slct.202202361]
[23]
Solangi, M.; Kanwal, Kh. Bioorg. Med. Chem., 2020, 28, 115605.
[http://dx.doi.org/10.1016/j.bmc.2020.115605] [PMID: 33065441]
[24]
Dhiman, A.; Sharma, R.; Singh, R.K. Acta Pharm. Sin. B, 2022, 12(7), 3006-3027.
[http://dx.doi.org/10.1016/j.apsb.2022.03.021] [PMID: 35865090]
[25]
Ke, S.; Yang, Z.; Zhang, Z.; Liang, Y.; Wang, K.; Liu, M.; Shi, L. Bioorg. Med. Chem. Lett., 2014, 24(8), 1907-1911.
[http://dx.doi.org/10.1016/j.bmcl.2014.03.011] [PMID: 24684840]
[26]
Aksenov, A.V.; Kirilov, N.K.; Arutiunov, N.A.; Aksenov, D.A.; Kuzminov, I.K.; Aksenov, N.A.; Turner, D.N.; Rogelj, S.; Kornienko, A.; Rubin, M. J. Org. Chem., 2022, 87(21), 13955-13964.
[http://dx.doi.org/10.1021/acs.joc.2c01627] [PMID: 36260110]
[27]
Abe, T.; Noda, K.; Sawada, D. Chem. Commun., 2021, 57(61), 7493-7496.
[http://dx.doi.org/10.1039/D1CC02821A] [PMID: 34212954]
[28]
Aksenov, D.A.; Akulova, A.S.; Aleksandrova, E.A.; Aksenov, N.A.; Leontiev, A.V.; Aksenov, A.V.; Aksenov, A.V. Molecules, 2023, 28(5), 2324.
[http://dx.doi.org/10.3390/molecules28052324] [PMID: 36903571]
[29]
Kornicka, A.; Gzella, K.; Garbacz, K.; Jarosiewicz, M.; Gdaniec, M.; Fedorowicz, J.; Balewski, Ł.; Kokoszka, J.; Ordyszewska, A. Pharmaceuticals, 2023, 16(7), 918.
[http://dx.doi.org/10.3390/ph16070918] [PMID: 37513830]
[30]
Kumar, M.; Goswami, A. Org. Lett., 2023, 25(18), 3254-3259.
[http://dx.doi.org/10.1021/acs.orglett.3c00987] [PMID: 37126068]
[31]
Kaplancıklı, Z.A.; Turan-Zitouni, G.; Özdemir, A.; Revial, G. Eur. J. Med. Chem., 2008, 43(1), 155-159.
[http://dx.doi.org/10.1016/j.ejmech.2007.03.019] [PMID: 17499887]
[32]
Huang, L.; Zheng, S.C.; Tan, B.; Liu, X.Y. Org. Lett., 2015, 17(6), 1589-1592.
[http://dx.doi.org/10.1021/acs.orglett.5b00479] [PMID: 25763688]
[33]
Abe, T.; Suzuki, T.; Anada, M.; Matsunaga, S.; Yamada, K. Org. Lett., 2017, 19(16), 4275-4278.
[http://dx.doi.org/10.1021/acs.orglett.7b01940] [PMID: 28762744]
[34]
Hirao, S.; Yamashiro, T.; Kohira, K.; Mishima, N.; Abe, T. Chem. Commun., 2020, 56(38), 5139-5142.
[http://dx.doi.org/10.1039/D0CC01210F] [PMID: 32253401]
[35]
Mahmoud, E.; Hayallah, A.M.; Kovacic, S.; Abdelhamid, D.; Abdel-Aziz, M. Pharmacol. Rep., 2022, 74(4), 570-582.
[http://dx.doi.org/10.1007/s43440-022-00370-3] [PMID: 35594012]
[36]
Fabitha, K.; Chandrakanth, M.; Pramod, R.N.; Arya, C.G.; Li, Y.; Banothu, J. ChemistrySelect, 2022, 7(21), e202201064.
[http://dx.doi.org/10.1002/slct.202201064]
[37]
Lakshmi, N.V.; Thirumurugan, P.; Noorulla, K.M.; Perumal, P.T. Bioorg. Med. Chem. Lett., 2010, 20(17), 5054-5061.
[http://dx.doi.org/10.1016/j.bmcl.2010.07.039] [PMID: 20675130]
[38]
Gunasekaran, P.; Balamurugan, K.; Sivakumar, S.; Perumal, S.; Menéndez, J.C.; Almansour, A.I. Green Chem., 2012, 14(3), 750.
[http://dx.doi.org/10.1039/c2gc16517a]
[39]
Rangel, J.; Díaz-Uribe, C.; Rodriguez-Serrano, A.; Zarate, X.; Serge, Y.; Vallejo, W.; Nogueras, M.; Trilleras, J.; Quiroga, J.; Tatchen, J.; Cobo, J. J. Mol. Struct., 2017, 1137, 431-439.
[http://dx.doi.org/10.1016/j.molstruc.2017.02.038]
[40]
Enriz, R.D.; Tosso, R.D.; Andújar, S.A.; Cabedo, N.; Cortés, D.; Nogueras, M.; Cobo, J.; Vargas, D.F.; Trilleras, J. Tetrahedron, 2018, 74(49), 7047-7057.
[http://dx.doi.org/10.1016/j.tet.2018.10.038]
[41]
Li, Y-H.; Zhao, B-L.; Gao, Y. Tetrahedron Asymmetry, 2014, 25, 1513.
[http://dx.doi.org/10.1016/j.tetasy.2014.10.012]
[42]
Zhao, K.; Xu, X.P.; Zhu, S.L.; Shi, D.Q.; Zhang, Y.; Ji, S.J. Synthesis, 2009, 16, 2697.
[43]
Olyaei, A.; Sadeghpour, M. RSC Advances, 2023, 13(31), 21710-21745.
[http://dx.doi.org/10.1039/D3RA04385A] [PMID: 37476036]
[44]
Hassaneen, H.M.; Hassaneen, H.M.E.; Gomaa, Z.A. Int. J. Org. Chem., 2011, 1(3), 97-104.
[http://dx.doi.org/10.4236/ijoc.2011.13015]
[45]
Baharfar, R.; Asghari, S.; Kiani, M. Monatsh. Chem., 2015, 146(2), 335-343.
[http://dx.doi.org/10.1007/s00706-014-1310-x]
[46]
Hossein nia, R.; Mamaghani, M.; Tabatabaeian, K.; Shirini, F.; Rassa, M. Bioorg. Med. Chem. Lett., 2012, 22(18), 5956-5960.
[http://dx.doi.org/10.1016/j.bmcl.2012.07.059] [PMID: 22892120]
[47]
Shiri, M.; Zolfigol, M.A.; Pirveysian, M.; Ayazi-Nasrabadi, R.; Kruger, H.G.; Naicker, T.; Mohammadpoor-Baltork, I. Tetrahedron, 2012, 68(30), 6059-6064.
[http://dx.doi.org/10.1016/j.tet.2012.05.006]
[48]
Nataraj, P.; Muralidharan, D.; Perumal, P.T. Tet. Lett., 2013, 54, 7091.
[49]
Slätt, J.; Janosik, T.; Wahlström, N.; Bergman, J. ChemInform, 2005, 42, 141.
[50]
Kreher, R.; Wagner, P.H. Chem. Ber., 1980, 113(11), 3675-3677.
[http://dx.doi.org/10.1002/cber.19801131127]
[51]
Slätt, J.; Romero, I.; Bergman, J. Synthesis, 2004, 2760.
[52]
Sobhani, S.; Parizi, Z.P. Tetrahedron, 2011, 67(19), 3540-3545.
[http://dx.doi.org/10.1016/j.tet.2011.03.014]
[53]
Zhou, F.; Hearne, Z.; Li, C.J. Curr. Opin. Green Sustain. Chem., 2019, 18, 118-123.
[http://dx.doi.org/10.1016/j.cogsc.2019.05.004]
[54]
Adeeyo, A.O.; Oyetade, J.A.; Alabi, M.A.; Adeeyo, R.O.; Samie, A.; Makungo, R. RSC Advances, 2023, 13(10), 6808-6826.
[http://dx.doi.org/10.1039/D2RA06596G] [PMID: 36865581]
[55]
De Rosa, M.; Soriente, A. Tetrahedron, 2011, 67(33), 5949-5955.
[http://dx.doi.org/10.1016/j.tet.2011.06.035]
[56]
Lu, J.; Ma, E.Q.; Liu, Y.H.; Li, Y.M.; Mo, L.P.; Zhang, Z.H. RSC Advances, 2015, 5(73), 59167-59185.
[http://dx.doi.org/10.1039/C5RA09517D]
[57]
Zhu, Y.S.; Shi, L.; Fu, L.; Chen, X.; Zhu, X.; Hao, X.Q.; Song, M.P. Chin. Chem. Lett., 2022, 33(3), 1497-1500.
[http://dx.doi.org/10.1016/j.cclet.2021.08.070]
[58]
Li, C.J.; Chen, L. Chem. Soc. Rev., 2006, 35(1), 68-82.
[http://dx.doi.org/10.1039/B507207G] [PMID: 16365643]
[59]
Cortes-Clerget, M.; Yu, J.; Kincaid, J.R.A.; Walde, P.; Gallou, F.; Lipshutz, B.H. Chem. Sci., 2021, 12(12), 4237-4266.
[http://dx.doi.org/10.1039/D0SC06000C]
[60]
Sheldon, R.A. Green Chem., 2017, 19(1), 18-43.
[http://dx.doi.org/10.1039/C6GC02157C]
[61]
Fatma, S.; Singh, D.; Ankit, P.; Mishra, P.; Singh, M.; Singh, J. Tet. Lett., 2014, 55, 2201.
[62]
Moshtaghi Zonouz, A.; Moghani, D.; Okhravi, S. Curr. Chem. Lett., 2014, 3(2), 71-74.
[http://dx.doi.org/10.5267/j.ccl.2014.2.001]
[63]
Moshtaghi Zonouz, A.; Moghani, D. Synth. Commun., 2016, 46(3), 220-225.
[http://dx.doi.org/10.1080/00397911.2015.1129668]
[64]
Moshtaghi Zonouz, A.; Okhravi, S.; Moghani, D. Monatsh. Chem., 2016, 147(10), 1819-1824.
[http://dx.doi.org/10.1007/s00706-016-1683-0]
[65]
Moshtaghi Zonouz, A.; Beiranvand, M.; Mohammad-Rezaei, R.; Naderi, S. Lett. Org. Chem., 2020, 17, 548.
[http://dx.doi.org/10.2174/1570178617666191111121813]
[66]
Slätt, J.; Janosik, T.; Wahlström, N.; Bergman, J. J. Heterocycl. Chem., 2005, 42(1), 141-145.
[http://dx.doi.org/10.1002/jhet.5570420122]
[67]
Venkatanarayana, M.; Dubey, P.K. J. Heterocycl. Chem., 2014, 51(4), 877-882.
[http://dx.doi.org/10.1002/jhet.1784]
[68]
Basha, K.N.U.; Gnanamani, S.; Shanmugam, P.; Venugopal, S.; Murthy, S.; Ramasamy, B. J. Heterocycl. Chem., 2021, 58, 2000.
[http://dx.doi.org/10.1002/jhet.4326]
[69]
Tarleton, M.; Dyson, L.; Gilbert, J.; Sakoff, J.A.; McCluskey, A. Bioorg. Med. Chem., 2013, 21(1), 333-347.
[http://dx.doi.org/10.1016/j.bmc.2012.10.003] [PMID: 23176751]

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