Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

A Review on the Syntheses and Applications of the 5H-chromeno[2,3- b]pyridines

Author(s): Ali Ramazani*, Mohammad Taghi Kiani and Sobhan Rezayati*

Volume 20, Issue 1, 2023

Published on: 06 September, 2022

Page: [28 - 53] Pages: 26

DOI: 10.2174/1570178619666220818151151

Price: $65

Abstract

5H-Chromeno[2,3-b]pyridine derivatives are a series of the most important compounds of chromenes with industrial, biological, and medicinal properties. These compounds are known as the privileged medicinal scaffold and can be synthesized by different methods such as multicomponent reactions (MCRs), Multicomponent coupling reactions (MCCRs), pot, atom, and step economy (PASE). In this review article, we have focused on the significant reactions for the syntheses and applications of 5H-chromeno[2,3-b] pyridines, including two-component reactions, three-component reactions, fourcomponent reactions, and multi-step reactions. This review is expected to serve as a useful conceptual overview and inspire the next generation to develop the different strategies for the preparation of 5HChromeno[ 2,3-b] pyridine derivatives.

Keywords: Chromenopyridines, privileged scaffold, multicomponent reactions, biological activity, antibacterial.

« Previous Next »
Graphical Abstract

[1]
Ren, Q.; Siau, W.Y.; Du, Z.; Zhang, K.; Wang, J. Chemistry, 2011, 17(28), 7781-7785.
[http://dx.doi.org/10.1002/chem.201100927] [PMID: 21618299]
[2]
Cheng, J.F.; Ishikawa, A.; Ono, Y.; Arrhenius, T.; Nadzan, A. Bioorg. Med. Chem. Lett., 2003, 13(21), 3647-3650.
[http://dx.doi.org/10.1016/j.bmcl.2003.08.025] [PMID: 14552749]
[3]
Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Eur. J. Med. Chem., 1993, 28(6), 517-520.
[http://dx.doi.org/10.1016/0223-5234(93)90020-F]
[4]
Gourdeau, H.; Leblond, L.; Hamelin, B.; Desputeau, C.; Dong, K.; Kianicka, I.; Custeau, D.; Boudreau, C.; Geerts, L.; Cai, S.X.; Drewe, J.; Labrecque, D.; Kasibhatla, S.; Tseng, B. Mol. Cancer Ther., 2004, 3(11), 1375-1384.
[PMID: 15542776]
[5]
Ali, T.E.S. Phosphorus Sulfur., 2007, 182(6), 1717-1726.
[http://dx.doi.org/10.1080/10426500701313896]
[6]
Moon, D.O.; Kim, K.C.; Jin, C.Y.; Han, M.H.; Park, C.; Lee, K.J.; Park, Y.M.; Choi, Y.H.; Kim, G.Y. Int. Immunopharmacol., 2007, 7(2), 222-229.
[http://dx.doi.org/10.1016/j.intimp.2006.10.001] [PMID: 17178390]
[7]
Chen, Y.J.; Huang, S.M.; Tai, M.C.; Chen, J.T.; Lee, A.R.; Huang, R.Y.; Liang, C.M. Pharmacol. Rep., 2020, 72(1), 115-125.
[http://dx.doi.org/10.1007/s43440-019-00026-9] [PMID: 32016832]
[8]
Mladenović, M.; Mihailović, M.; Bogojević, S.; Matić, Nićiforović, N.; Mihailović, V.; Vuković, N.; Sukdolak, S.; Solujić, S. Int. J. Mol. Sci., 2011, 12(5), 2822-2841.
[PMID: 21686153]
[9]
Rueping, M.; Sugiono, E.; Merino, E. Chemistry, 2008, 14(21), 6329-6332.
[http://dx.doi.org/10.1002/chem.200800836] [PMID: 18576457]
[10]
Ramazani, A.; Ahmadi, Y.; Aghahosseini, H.; Joo, S.W. Phosphorus Sulfur Silicon Relat. Elem., 2016, 191(3), 354-358.
[http://dx.doi.org/10.1080/10426507.2015.1072193]
[11]
Ghoneim, A.A.; El-Farargy, A.F.; Abdelaziz, S. Nucleosides Nucleotides Nucleic Acids, 2014, 33(9), 583-596.
[http://dx.doi.org/10.1080/15257770.2014.912320] [PMID: 25105450]
[12]
Patel, A.A.; Lad, H.B.; Pandya, K.R.; Patel, C.V.; Brahmbhatt, D.I. Med. Chem. Res., 2013, 22, 4745-4754.
[http://dx.doi.org/10.1007/s00044-013-0489-4]
[13]
Jadhav, G.R.; Deshmukh, D.G.; Medhane, V.J.; Gaikwad, V.B.; Bholay, A.D. Heterocycl. Commun., 2016, 22(3), 123-130.
[http://dx.doi.org/10.1515/hc-2015-0215]
[14]
Mori, J.; Iwashima, M.; Takeuchi, M.; Saito, H. Chem. Pharm. Bull. (Tokyo), 2006, 54(3), 391-396.
[http://dx.doi.org/10.1248/cpb.54.391] [PMID: 16508200]
[15]
Jain, N.; Xu, J.; Kanojia, R.M.; Du, F.; Jian-Zhong, G.; Pacia, E.; Lai, M.T.; Musto, A.; Allan, G.; Reuman, M.; Li, X.; Hahn, D.; Cousineau, M.; Peng, S.; Ritchie, D.; Russell, R.; Lundeen, S.; Sui, Z. J. Med. Chem., 2009, 52(23), 7544-7569.
[http://dx.doi.org/10.1021/jm900146e] [PMID: 19366247]
[16]
Amr, A.G.; Mohamed, A.M.; Mohamed, S.F.; Abdel-Hafez, N.A.; Hammam, Ael-F. Bioorg. Med. Chem., 2006, 14(16), 5481-5488.
[http://dx.doi.org/10.1016/j.bmc.2006.04.045] [PMID: 16713269]
[17]
Bhat, M.A.; Siddiqui, N.; Khan, S.A. Acta Pol. Pharm., 2008, 65(2), 235-239.
[PMID: 18666431]
[18]
El-Sayed, R.; Fadda, A.A. J. Oleo Sci., 2016, 65(11), 929-940.
[http://dx.doi.org/10.5650/jos.ess15300] [PMID: 27803492]
[19]
Uesawa, Y.; Ishii-Nozawa, R.; Ishihara, M.; Kagaya, H.; Kanamoto, T.; Terakubo, S.; Nakashima, H.; Takao, K.; Sugita, Y.; Sakagami, H. Anticancer Res., 2014, 34(10), 5405-5411.
[PMID: 25275035]
[20]
Ryzhkova, Y.E.; Ryzhkov, F.V.; Elinson, M.N.; Vereshchagin, A.N.; Egorov, M.P. ARKIVOC, 2020, vi, 193-208.
[http://dx.doi.org/10.24820/ark.5550190.p011.220]
[21]
Banerjee, S.; Wang, J.; Pfeffer, S.; Ma, D.; Pfeffer, L.M.; Patil, S.A.; Li, W.; Miller, D.D. Molecules, 2015, 20(9), 17152-17165.
[http://dx.doi.org/10.3390/molecules200917152] [PMID: 26393554]
[22]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Egorov, M.P.P. Compd., 2020, 40(1), 108-115.
[23]
Chake, A.; Zribi, F.; Nepveu, F.; Chabchoub, F. Chin. Chem. Lett., 2014, 25(8), 1207-1210.
[http://dx.doi.org/10.1016/j.cclet.2014.03.048]
[24]
Heravi, M.M.; Ansari, P.; Saeedi, M.; Tavakoli-Hosseini, N.; Karimi, N. Bull. Chem. Soc. Ethiop., 2011, 25(2), 315-320.
[http://dx.doi.org/10.4314/bcse.v25i2.65915]
[25]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Krymov, S.K.; Fakhrutdinov, A.N.; Egorov, M.P. Monatsh. Chem., 2019, 150, 1073-1078.
[http://dx.doi.org/10.1007/s00706-019-02388-5]
[26]
Kamboj, S.; Singh, R. Arab. J. Sci. Eng., 2022, 47, 75-111.
[http://dx.doi.org/10.1007/s13369-021-05858-3]
[27]
Evdokimov, N.M.; Kireev, A.S.; Yakovenko, A.A.; Antipin, M.Y.; Magedov, I.V.; Kornienko, A. J. Org. Chem., 2007, 72(9), 3443-3453.
[http://dx.doi.org/10.1021/jo070114u] [PMID: 17408286]
[28]
Choi, J.S.; Shi, S.C. Biomol. Ther. (Seoul), 2008, 16(3), 210-214.
[http://dx.doi.org/10.4062/biomolther.2008.16.3.210]
[29]
Katsarou, M.E.; Efthimiadou, E.K.; Psomas, G.; Karaliota, A.; Vourloumis, D. J. Med. Chem., 2008, 51(3), 470-478.
[http://dx.doi.org/10.1021/jm7013259] [PMID: 18205294]
[30]
Tang, G.M.; Han, J.Y.; Wang, Y.T.; Cui, Y.Z.; Ng, S.W. Polyhedron, 2017, 133(5), 336-342.
[http://dx.doi.org/10.1016/j.poly.2017.05.031]
[31]
Anderson, D.R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W.F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P.A.; Masih, L. Bioorg. Med. Chem. Lett., 2005, 15(6), 1587-1590.
[http://dx.doi.org/10.1016/j.bmcl.2005.01.067] [PMID: 15745802]
[32]
Verma, C.; Olasunkanmi, L.O.; Obot, I.B.; Ebensob, E.E.; Quraishi, M.A. RSC Advances, 2016, 6, 53933-53948.
[http://dx.doi.org/10.1039/C6RA04900A]
[33]
Zhang, C.H.; Huang, R.; Hu, X.M.; Lin, J.; Yan, S.J. J. Org. Chem., 2018, 83(9), 4981-4989.
[http://dx.doi.org/10.1021/acs.joc.8b00099] [PMID: 29648823]
[34]
Elinson, M.; Vereshchagin, A.N.; Anisina, Y.E.; Goloveshkin, A.S.; Ushakov, I.E.; Egorov, M.P. Russ. Chem. Bull., 2018, 67, 1695-1703.
[http://dx.doi.org/10.1007/s11172-018-2278-1]
[35]
Nikookar, H.; Moghimi, S.; Sayahi, M.H.; Mahdavi, M.; Ranjbar, P.R.; Firoozpour, L.; Foroumadi, A. Comb, 2018, 21(5), 344-348.
[http://dx.doi.org/10.2174/1386207321666180524110635]
[36]
Gorokhov, V.Y.; Makhova, T. Russ. Chem. Bull., 2020, 69, 425-434.
[http://dx.doi.org/10.1007/s11172-020-2781-z]
[37]
(a) Yavari, I.; Ramazani, A. Phosphorus Sulfur, 1997, 130(1), 73-77.
[http://dx.doi.org/10.1080/10426509708033699];
(b) Mohamadpour, F.; Feilizadeh, M. Chem. Methodol., 2020, 4(5), 647-659.;
(c) Belgasem Mezoughi, A.; Abdussalam Mohammed, W.; Ettarhouni, Z.O. J. Chem. Rev., 2021, 3(3), 196-218.
[38]
(a) Azizmohammadi, M.; Khoobi, M.; Ramazani, A.; Emami, S.; Zarrin, A.; Firuzi, O.; Miri, R.; Shafiee, A. Eur. J. Med. Chem., 2013, 59, 15-22.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.044] [PMID: 23202485];
(b) Sapra, R.; Patel, D.; Meshram, D. J. Med. Chem. Sci., 2020, 3(1), 71-78.
[http://dx.doi.org/10.26655/JMCHEMSCI.2020.1.9];
(c) Asirvatham, S.; Thakor, E.; Jain, H. J. Chem. Rev., 2021, 3(4), 247-272.
[http://dx.doi.org/10.22034/jcr.2021.295839.1123]
[39]
Khoobi, M.; Ma’mani, L.; Rezazadeh, F.; Zareie, Z.; Foroumadi, A.; Ramazani, A.; Shafiee, A. J. Mol. Catal. Chem., 2012, 359, 74-80.
[http://dx.doi.org/10.1016/j.molcata.2012.03.023]
[40]
(a) Ramazani, A.; Shajari, N.; Mahyari, A.; Ahmadi, Y. Mol. Divers., 2011, 15(2), 521-527.
[http://dx.doi.org/10.1007/s11030-010-9275-0] [PMID: 20812029];
(b) Irannejad-Gheshlaghchaei, N.; Zare, A.; Banaei, A.; Kaveh, H.; Varavi, N. Chem. Methodol., 2020, 4(4), 400-407.
[http://dx.doi.org/10.33945/SAMI/CHEMM.2020.4.3];
(c) Muhiebes, R.M.; Al-Tamimi, E.O. Chem. Methodol., 2021, 5(5), 416-421.;
(d) Fadel, Z.H.; Al-Azzawi, A.M. Chem. Methodol., 2021, 5(6), 464-470.;
(e) Baghernejad, B.; Nazari, L. Chem. Commun. (Camb.), 2021, 3(5), 319-326.;
(f) Baghernejad, B.; Rostami Harzevili, M. Chem. Methodol., 2021, 5(2), 90-95.;
(g) Karimi, A.H.; Hekmat-Ara, A.; Zare, A.; Barzegar, M.; Khanivar, R.; Sadeghi-Takallo, M. Chem. Commun. (Camb.), 2021, 3(6), 360-368.;
(h) Nikpassand, M.; Zare Fekri, L. Chem. Methodol., 2020, 4(4), 437-446.
[http://dx.doi.org/10.33945/SAMI/CHEMM.2020.4.6]
[41]
(a) Ramazani, A.; Mahyari, A.T.; Rouhani, M.; Rezaei, A. Tetrahedron Lett., 2009, 50(40), 5625-5627.
[http://dx.doi.org/10.1016/j.tetlet.2009.07.115];
(b) Khazaei, A.; Gohari-Ghalil, F.; Tavasoli, M.; Rezaei-Gohar, M.; Moosavi-Zare, A.R. Chem. Methodol, 2020, 4(5), 543-553.;
(c) Kamali, F.; Shirini, F. Chem. Commun. (Camb.), 2021, 3(4), 278-290.;
(d) Fernandes, C.; Park, S.H.; Sloop, J.; Wilmott, K. Chem. Methodol., 2020, 4(5), 554-564.;
(e) Albadi, J.; Samimi, H.A.; Momeni, A.R. Chem. Methodol, 2020, 4(5), 565-571.;
(f) Moosavi-Zare, A.R.; Zolfigol, M.A.; Rezanejad, Z. Chem. Methodol., 2020, 4(5), 614-622.;
(g) Hoseini, Z.; Davoodnia, A.; Pordel, M. Advanced Journal of Chemistry, Section A, 2021, 4(1), 68-77.;
(h) Rehan, T.A.; Al-Lami, N.; Khudhair, N.A. Chem. Methodol., 2021, 5(4), 285-295.
[42]
(a) Baghernejad, B.; Zareie, A.; Asian, J. Green Chem., 2021, 5(4), 343-350.;
(b) Rezayati, S.; Kalantari, F.; Ramazani, A.; Sajjadifar, S.; Aghahosseini, H.; Rezaei, A. Inorg. Chem., 2022, 61(2), 992-1010.
[http://dx.doi.org/10.1021/acs.inorgchem.1c03042] [PMID: 34962386];
(c) Singha, R.; Brahman, D.; Sinha, B.; Ghosh, P.; Asian, J. Green Chem., 2021, 5(1), 91-110.;
(d) Fallah-Mehrjardi, M.; Foroughi, M.; Banitaba, S.H.; Asian, J. Green Chem., 2020, 4(1), 75-86.;
(e) Rezayati, S.; Ramazani, A.; Sajjadifar, S.; Aghahosseini, H.; Rezaei, A. ACS Omega, 2021, 6(39), 25608-25622.
[http://dx.doi.org/10.1021/acsomega.1c03672] [PMID: 34632217];
(f) Baghernejad, B.; Talebi, M.; Asian, J. Green Chem., 2021, 5(4), 368-377.;
(g) Majidi Arlan, F.; Javahershenas, R.; Khalafy, J. Asian J. Nanosci. Mater., 2020, 3(3), 238-250.;
(h) Kalantari, F.; Rezayati, S.; Ramazani, A.; Aghahosseini, H.; Ślepokura, K.; Lis, T. ACS Appl. Nano Mater., 2022, 5(2), 1783-1797.
[http://dx.doi.org/10.1021/acsanm.1c03169];
(i) Pagore, V.P.; Jadhav, V.B.; Bajad, P.N.; Pawar, R.P.; Asian, J. Green Chem., 2020, 4(4), 379-386. (j) Yadollahzadeh. K. Asian J. Nanosci. Mater., 2021, 4(1), 81-94.
[43]
(a) Butler, R.N.; Coyne, A.G. Org. Biomol. Chem., 2016, 14(42), 9945-9960.
[http://dx.doi.org/10.1039/C6OB01724J] [PMID: 27714194];
(b) Rezayati, S.; Salehi, E.; Hajinasiri, R.; Afshari Sharif Abad, S. C. R. Chim., 2017, 20(5), 554-558.
[http://dx.doi.org/10.1016/j.crci.2016.07.004];
(c) Rezayati, S.; Hajinasiri, R.; Erfani, Z. Res. Chem. Intermed., 2016, 42, 2567-2576.
[http://dx.doi.org/10.1007/s11164-015-2168-1]
[44]
Elinson, M.N.; Nasybullin, R.F.; Ryzhkov, F.V.; Zaimovskaya, T.A.; Nikishin, G.I. Monatshefte für Chemie-Chemical Monthly, 2015, 146, 631-635.
[http://dx.doi.org/10.1007/s00706-014-1318-2]
[45]
Nouri, H.; Cadiou, C.; HenryaIsabelle, A.; Déchamps-Oliviera, I.; Ternane, R.; Trabelsi-Ayadi, M.; Lemercier, G.; Chuburu, F. J. Lumin., 2014, 148, 202-206.
[http://dx.doi.org/10.1016/j.jlumin.2013.12.027]
[46]
de Silva, A.P.; Gunaratne, H.Q.; Gunnlaugsson, T.; Huxley, A.J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Chem. Rev., 1997, 97(5), 1515-1566.
[http://dx.doi.org/10.1021/cr960386p] [PMID: 11851458]
[47]
Weinstein, D.S.; Gong, H.; Doweyko, A.M.; Cunningham, M.; Habte, S.; Wang, H. J. Med. Chem., 2011, 54(20), 7318-7333.
[http://dx.doi.org/10.1021/jm200879j] [PMID: 21899328]
[48]
Gong, H.; Yang, Z. Bioorg. Med. Chem. Lett., 2014, 24(15), 3268-3273.
[http://dx.doi.org/10.1016/j.bmcl.2014.06.010] [PMID: 24980053]
[49]
Osyanin, V.A.; Osipov, D.V.; Klimochkin, Y.N. Tetrahedron, 2012, 68(27-28), 5612-5618.
[http://dx.doi.org/10.1016/j.tet.2012.04.065]
[50]
Bardasov, I.N.; Alekseeva, A.Y.; Malyshkina, N.L.; Ershov, O.V.; Grishanov, D.A. Russ. J. Org. Chem., 2016, 52, 830-833.
[http://dx.doi.org/10.1134/S1070428016060117]
[51]
Yunnikova, L.P.; Gorokhov, V.Y.; Makhova, T.V.; Aleksandrova, G.A. Pharm. Chem. J., 2013, 47, 139-141.
[http://dx.doi.org/10.1007/s11094-013-0912-7]
[52]
Festa, A.A.; Storozhenko, O.A.; Bella Ndoutoume, D.R.; Varlamov, A.V.; Voskressensky, L.G. Mendeleev Commun., 2017, 27, 451-453.
[http://dx.doi.org/10.1016/j.mencom.2017.09.006]
[53]
Elinson, M.N.; Gorbunov, S.V.; Vereshchagin, A.N.; Nasybullin, R.F.; Goloveshkin, A.S.; Bushmarinov, I.S.; Egorov, M.P. Tetrahedron, 2014, 70(45), 8559-8563.
[http://dx.doi.org/10.1016/j.tet.2014.09.066]
[54]
Clarke, P.A.; Santos, S.; Martin, W.H. Green Chem., 2007, 9(5), 438-440.
[http://dx.doi.org/10.1039/b700923b]
[55]
Hayashi, Y. Chem. Sci. (Camb.), 2016, 7, 866-880.
[http://dx.doi.org/10.1039/C5SC02913A]
[56]
Bhattacharyya, P.; Pradhan, K.; Paul, S.; Das, A.R. Tetrahedron Lett., 2012, 53(35), 4687-4691.
[http://dx.doi.org/10.1016/j.tetlet.2012.06.086]
[57]
Mishra, S.; Ghosh, R. Synth. Commun., 2012, 42(15), 2229-2244.
[http://dx.doi.org/10.1080/00397911.2011.555284]
[58]
Ghasemzadeh, M.A.; Abdollahi-Basir, M.H.; Babaei, M. Green Chem. Lett. Rev., 2015, 8(3-4), 40-49.
[http://dx.doi.org/10.1080/17518253.2015.1107139]
[59]
Elinson, M.N.; Ilovaisky, A.I.; Merkulova, V.M.; Belyakov, P.A.; Chizhov, A.O.; Nikishin, G.I. Tetrahedron, 2010, 66(23), 4043-4048.
[http://dx.doi.org/10.1016/j.tet.2010.04.024]
[60]
Vereshchagin, A.N.; Elinson, M.N.; Anisina, Y.E.; Ryzhkov, F.V.; Goloveshkin, A.S.; Bushmarinov, I.S.; Zlotin, S.G. Mendeleev Commun., 2015, 6, 424-426.
[http://dx.doi.org/10.1016/j.mencom.2015.11.008]
[61]
Poupaert, J.; Carato, P.; Colacino, E.; Yous, S. Curr. Med. Chem., 2005, 12(7), 877-885.
[http://dx.doi.org/10.2174/0929867053507388] [PMID: 15853716]
[62]
Perez-Fernandez, R.; Goya, P.; Elguero, J. ARKIVOC, 2014, ii, 233-293.
[63]
Wise, L.D.; Butler, D.E.; DeWald, H.A.; Lustgarten, D.M.; Pattison, I.C.; Schweiss, D.N.; Coughenour, L.L.; Downs, D.A.; Heffner, T.G.; Pugsley, T.A. J. Med. Chem., 1987, 30(10), 1807-1812.
[http://dx.doi.org/10.1021/jm00393a021] [PMID: 2888897]
[64]
Singh, P.; Paul, K.; Holzer, W. Bioorg. Med. Chem., 2006, 14(14), 5061-5071.
[http://dx.doi.org/10.1016/j.bmc.2006.02.046] [PMID: 16554161]
[65]
Kees, K.L.; Fitzgerald, J.J., Jr; Steiner, K.E.; Mattes, J.F.; Mihan, B.; Tosi, T.; Mondoro, D.; McCaleb, M.L. J. Med. Chem., 1996, 39(20), 3920-3928.
[http://dx.doi.org/10.1021/jm960444z] [PMID: 8831758]
[66]
Herk, T.V.; Brussee, J.; van den Nieuwendijk, A.M.C.H.; van der Klein, P.A.M.; IJzerman, A.P.; Stannek, C.; Burmeister, A.; Lorenzen, A. J. Med. Chem., 2003, 46(18), 3945-3951.
[http://dx.doi.org/10.1021/jm030888c] [PMID: 12930155]
[67]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Fakhrutdinov, A.N.; Goloveshkin, A.S.; Egorov, M.P. J. Fluor. Chem., 2018, 213, 31-36.
[http://dx.doi.org/10.1016/j.jfluchem.2018.06.008]
[68]
Elinson, M.N.; Vereshchagin, A.N.; Anisina, Y.E.; Fakhrutdinov, A.N.; Goloveshkin, A.S.; Egorov, M.P. Eur. J. Org. Chem., 2019, 2019(26), 4171-4178.
[http://dx.doi.org/10.1002/ejoc.201900240]
[69]
Quin, L.D. A guide to organophosphorus chemistry; John Wiley & Sons, 2000.
[70]
Hildebrand, R. The Role of Phosphonates in Living Systems, 1983, 139-169.
[http://dx.doi.org/10.1201/9781351076470]
[71]
Benbrook, C.M. Environ. Sci. Eur., 2016, 28(1), 3.
[http://dx.doi.org/10.1186/s12302-016-0070-0] [PMID: 27752438]
[72]
Paliwal, P.; Jetti, S.R.; Bhatewara, A.; Kadre, T.; Jain, S. ISRN Org. Chem., 2013, 2013, 526173.
[http://dx.doi.org/10.1155/2013/526173] [PMID: 24052863]
[73]
Gupta, S.; Khurana, J.M. Green Chem., 2017, 19, 4153-4156.
[http://dx.doi.org/10.1039/C7GC01463E]
[74]
Olyaei, A.; Shahsavari, M.S.; Sadeghpour, M. Res. Chem. Intermed., 2018, 44, 943-956.
[http://dx.doi.org/10.1007/s11164-017-3145-7]
[75]
Zhang, W.; Wang, J.; Mao, J.; Hu, L.; Wu, X.; Guo, C. Tetrahedron Lett., 2016, 57, 1985-1989.
[http://dx.doi.org/10.1016/j.tetlet.2016.03.081]
[76]
Chung, S.T.; Huang, W.H.; Huang, C.K.; Liu, F.C.; Huang, R.Y.; Wu, C.C.; Lee, A.R. Res. Chem. Intermed., 2016, 42, 1195-1215.
[http://dx.doi.org/10.1007/s11164-015-2081-7]
[77]
Vereshchagin, A.N.; Elinson, M.N.; Anisina, Y.E.; Ryzhkov, F.V.; Novikov, R.A.; Egorov, M.P. ChemistrySelect, 2017, 2(17), 4593-4597.
[http://dx.doi.org/10.1002/slct.201700606]
[78]
Ansari, K.; Quraishi, M.; Singh, A. J. Assoc. Arab Univ. Basic Appl. Sci., 2017, 22, 45-54.
[79]
Zhang, M.; Chen, M.N.; Zhang, Z.H. Adv. Synth. Catal., 2019, 361(22), 5182-5190.
[http://dx.doi.org/10.1002/adsc.201900994]
[80]
Safaei-Ghomi, J.; Tavazo, M.; Vakili, M.R.; Shahbazi-Alavi, H. J. Sulfur Chem., 2017, 38(3), 236-248.
[http://dx.doi.org/10.1080/17415993.2016.1275633]
[81]
Sudheesh, N.; Sharma, S.K.; Shukla, R.S. J. Mol. Catal. Chem., 2010, 321(1-2), 77-82.
[http://dx.doi.org/10.1016/j.molcata.2010.02.005]
[82]
Abdelmoniem, A.M.; Ghozlan, S.A.S.; Abdelmoniem Ahmed, D.M.; Elwahy, H.M.; Abdelhamid, I.A. J. Heterocycl. Chem., 2017, 54(5), 2844-2849.
[http://dx.doi.org/10.1002/jhet.2890]
[83]
Rajanarendar, E.; Ramakrishna, S.; Kishore, B. J. Heterocycl. Chem., 2014, 51(5), 1415-1420.
[http://dx.doi.org/10.1002/jhet.1836]
[84]
Dineen, T.A.; Chen, K.; Cheng, A.C.; Derakhchan, K.; Epstein, O.; Esmay, J.; Hickman, D.; Kreiman, C.E.; Marx, I.E.; Wahl, R.C.; Wen, P.H.; Weiss, M.M.; Whittington, D.A.; Wood, S.; Fremeau, R.T., Jr; White, R.D.; Patel, V.F. J. Med. Chem., 2014, 57(23), 9811-9831.
[http://dx.doi.org/10.1021/jm5012676] [PMID: 25363711]

Rights & Permissions Print Cite
Article Metrics
3
© 2024 Bentham Science Publishers | Privacy Policy