Synthesis of N-aryl 2-chloroacetamides and their chemical reactivity towards various types of nucleophiles

References

• Micky, J. A. A.; Saleh, N. M. S.; Mohamed, M.; Mohameda, S. A.; Salem, M. M. Indian J. Chem. 2006, 45, 1579–1583.
   Google Scholar
• Duckworth, C. A. Stable emulsion flowable formulation of a 2-chloroacetamide herbicide and an imidazolinone herbicide. U. S. Patent 5,538,938, 1996.
   Google Scholar
• Ikeuchi, T.; Ohkawa, T.; Ohno, S.; Yamaji, Y.; Ogawa, Y. Phytotoxicity controlling agent for upland farming and phytotoxicity controlling method using the same. U.S. Patent 8,318,635, 2012.
   Google Scholar
• Concellón, J. M.; Rodríguez-Solla, H.; del Amo, V.; Diaz, P. J.Org. Chem. 2010, 75, 2407–2410. DOI: 10.1021/jo902708x.
   PubMed Web of Science ®Google Scholar
• Guthrie, D. B.; Damodaran, K.; Curran, D. P.; Wilson, P.; Clark, A. J. J. Org. Chem. 2009, 74, 4262–4266. DOI: 10.1021/jo900491w.
   PubMed Web of Science ®Google Scholar
• O’Reilly, E.; Lestini, E.; Balducci, D.; Paradisi, F. Tetrahedron Lett. 2009, 50, 1748–1750. DOI: 10.1016/j.tetlet.2009.01.146.
   Web of Science ®Google Scholar
• Paczal, A.; Bényei, A. C.; Kotschy, A. J. Org. Chem. 2006, 71, 5969–5979. DOI: 10.1021/jo060594+.
   PubMed Web of Science ®Google Scholar
• Busato, S.; Craig, D. C.; Judeh, Z. M.; Read, R. W. Tetrahedron. 2003, 59, 461–472. DOI: 10.1016/S0040-4020(02)01535-1.
   Web of Science ®Google Scholar
• Zaragoza, F.; Stephensen, H. J. Org. Chem. 1999, 64, 2555–2557. DOI: 10.1021/jo982070i.
   Web of Science ®Google Scholar
• Sirasani, G.; Andrade, R. B. Org. Lett. 2009, 11, 2085–2088. DOI: 10.1021/ol9004799.
   PubMed Web of Science ®Google Scholar
• Kaoudi, T.; Miranda, L. D.; Zard, S. Z. Org. Lett. 2001, 3, 3125–3127. DOI: 10.1021/ol016424v.
   PubMed Web of Science ®Google Scholar
• Evans, M. J.; Cravatt, B. F. Chem. Rev. 2006, 106, 3279–3301. DOI: 10.1021/cr050288g.
   PubMed Web of Science ®Google Scholar
• Abdel-Latif, E.; Radwan, A. S.; Karam, M.; Ismail, M. A. Indian J. Heterocycl. Chem. 2018, 28, 495–501.
   Web of Science ®Google Scholar
• Abdel-Latif, E.; Keshk, E. M.; Khalil, A. G. M.; Saeed, A.; Metwally, H. M. J. Heterocyclic Chem. 2018, 55, 2334–2341. DOI: 10.1002/jhet.3294.
   Web of Science ®Google Scholar
• Altalbawy, F. IJMS. 2013, 14, 2967–2979. DOI: 10.3390/ijms14022967.
   Google Scholar
• Zubkov, V. A.; Tsapko, T. A.; Gritsenko, I. S.; Maloshtan, L. N. Russ. Chem. Bull. 2010, 59, 2329–2332. DOI: 10.1007/s11172-010-0396-5.
   Web of Science ®Google Scholar
• Shaul, M.; Abourbeh, G.; Jacobson, O.; Rozen, Y.; Laky, D.; Levitzki, A.; Mishani, E. Bioorg. Med. Chem. 2004, 12, 3421–3429. DOI: 10.1016/j.bmc.2004.04.044.
   PubMed Web of Science ®Google Scholar
• Sonmez, H. B.; Bicak, N. React. Funct. Polym. 2002, 51, 55–60. DOI: 10.1016/S1381-5148(02)00033-0.
   Web of Science ®Google Scholar
• Borisa, A.; Bhatt, H. G.; Thakkar, D.; Trivedi, S. Wjpps. 2015, 4, 928–941. DOI: 10.20959/wjpps20174-8951.
   Google Scholar
• Tailor, J. H.; Patel, P. C.; Malik, G. M. Indian J. Chem. 2014, 53B, 1263–1268.
   Google Scholar
• Katke, S. A.; Amrutkar, S. V.; Bhor, R. J.; Khairnar, M. V. IJPSR. 2011, 2, 148–156.
   Google Scholar
• Shukla, M. B.; Mahyavanshi, J. B.; Parmar, K. A. Indian J. Chem. 2016, 55B, 374–380.
   Google Scholar
• Jayaramu, P. K.; Maralihallia, R. R. Der Pharma Chemica. 2015, 7, 30–35.
   Google Scholar
• Anthwal, A.; Thakur, B. K.; Rawat, M. S. M. J. Indian Chem. Soc. 2014, 91, 1525–1531.
   Web of Science ®Google Scholar
• Erol, I. J. Polym. Sci. A Polym. Chem. 2004, 42, 3157–3169. DOI: 10.1002/pola.20132.
   Web of Science ®Google Scholar
• Joshi, D.; Parikh, K. S. Med. Chem. Res. 2014, 23, 1855–1864. DOI: 10.1007/s00044-013-0791-1.
   Web of Science ®Google Scholar
• Harte, A. J.; Gunnlaugsson, T. Tetrahedron Lett. 2006, 47, 6321–6324. DOI: 10.1016/j.tetlet.2006.06.090.
   Web of Science ®Google Scholar
• Torrens, A.; Mas, J.; Port, A.; Castrillo, J. A.; Sanfeliu, O.; Guitart, X.; Dordal, A.; Romero, G.; Fisas, M. A.; Sánchez, E.; et al. J. Med. Chem. 2005, 48, 2080–2092., DOI: 10.1021/jm049599u.
   PubMed Web of Science ®Google Scholar
• Ahmed, E. M.; Taha, N. M.; El-Gawad, S. A.; Nady, N. M. S. Der. Chem. Sin. 2011, 2, 197–210.
   Google Scholar
• Bhausaheb, D. K.; Madhukar, G. V.; Balkrishna, S. S. IJPPR. 2015, 3, 112–124.
   Google Scholar
• Georgey, H. Molecules. 2014, 19, 3777–3792. DOI: 10.3390/molecules19033777.
   PubMed Web of Science ®Google Scholar
• Elzahabi, H. S. A.; Salem, M. A.; Thabet, H. K. Der Pharma. Chemica. 2011, 3, 48–58.
   Google Scholar
• Venkov, A. P.; Minkov, M.; Lukanov, M.; Synth, L. K. Commun. 1989, 19, 2133–2139. DOI: 10.1080/00397918908052608.
   Google Scholar
• Chupp, J. P.; Olin, J. F.; Landwehr, H. K. J. Org. Chem. 1969, 34, 1192–1197. DOI: 10.1021/jo01257a003.
   Web of Science ®Google Scholar
• Zupancic, B. G.; Sopcic, M. Synthesis. 1982, 942–944. DOI: 10.1055/s-1982-30008.
   Web of Science ®Google Scholar
• Blaser, H.-U.; Pugin, B.; Spindler, F.; Thommen, M. Acc. Chem. Res. 2007, 40, 1240–1250. DOI: 10.1021/ar7001057.
   PubMed Web of Science ®Google Scholar
• Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 17–31. DOI: 10.1002/1615-4169(200201)344.
   Web of Science ®Google Scholar
• Blaser, H.-U.; Buser, H.-P.; Coers, K.; Hanreich, R.; Jalett, H.-P.; Jelsch, E.; Pugin, B.; Schneider, H.-D.; Spindler, F.; Wegmann, A. Chimia. 1999, 53, 275–280.
   Web of Science ®Google Scholar
• Blaser, H.-U.; Spindler, F. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999.
   Google Scholar
• Blaser, H.-U. Chimia (Aarau). 2015, 69, 393–406. DOI: 10.2533/chimia.2015.393.
   Web of Science ®Google Scholar
• Pugin, B.; Landert, H.; Spindler, F.; Blaser, H.-U. Adv. Synth. Catal. 2002, 344, 974–979. DOI: 10.1002/1615-4169(200210)344.
   Web of Science ®Google Scholar
• Spindler, F.; Früh, T. Chirality in Agrochemicals; John Wiley & Sons Ltd.: Chichester, 1998.
   Google Scholar
• Huang, B.; Li, X.; Zhan, P.; De Clercq, E.; Daelemans, D.; Pannecouque, C.; Liu, X. Chem. Biol. Drug Des. 2016, 87, 283–289. DOI: 10.1111/cbdd.12657.
   PubMed Web of Science ®Google Scholar
• Ma, L.; Li, S.; Zheng, H.; Chen, J.; Lin, L.; Ye, X.; Chen, Z.; Xu, Q.; Chen, T.; Yang, J.; et al. Eur. J. Med. Chem. 2011, 46, 2003–2010. DOI: 10.1016/j.ejmech.2011.02.033.
   PubMed Web of Science ®Google Scholar
• Borisov, A. V.; Dzhavakhishvili, S. G.; Zhuravel, I. O. S.; Kovalenko, M.; Nikitchenko, V. M. J. Comb. Chem. 2007, 9, 5–8. DOI: 10.1021/cc060103z.
   PubMed Web of Science ®Google Scholar
• Moustafa, M. A.; Gineinah, M. M.; Nasr, M. N.; Bayoumi, W. A. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 427–433. DOI: 10.1002/ardp.200300847.
   PubMed Web of Science ®Google Scholar
• Abbas, S. E.; Abdel Gawad, N. M.; Georgey, H. H.; Abdullah, J. H. Int. J. Chemtech Res. 2010, 2, 1560–1578.
   Google Scholar
• Kryshchyshyn, A.; Atamanyuk, D.; Lesyk, R. Sci. Pharm. 2012, 80, 509–530. DOI: 10.3797/scipharm.1204-02.
   PubMedGoogle Scholar
• Lamie, P. F.; Ali, W. A.; Bazgier, V.; Rárová, L. Eur. J. Med. Chem. 2016, 123, 803–813. DOI: 10.1016/j.ejmech.2016.08.013.
   PubMed Web of Science ®Google Scholar
• Inam, A.; Van Zyl, R. L.; van Vuuren, N. J.; Chen, C. T.; Avecilla, F.; Agarwal, S. M.; Azam, A. RSC Adv. 2015, 5, 48368–48381. DOI: 10.1039/c5ra05472a.
   Web of Science ®Google Scholar
• El-Sabbagh, O. I. Arch. Pharm. Chem. Life. Sci. 2013, 346, 733–742. DOI: 10.1002/ardp.201300110.
   PubMed Web of Science ®Google Scholar
• Hamama, W. S.; Ibrahim, M. E.; Zoorob, H. H. J. Chinese Chem. Soc. 2017, 64, 1203–1212. DOI: 10.1002/jccs.201700064.
   Web of Science ®Google Scholar
• Shaaban, O. G.; Rizk, O. H.; Bayad, A. E.; El-Ashmawy, I. M. TOMCJ. 2013, 7, 49–65. DOI: 10.2174/1874104501307010049.
   Google Scholar
• Ren, J. L.; Zhang, X. Y.; Yu, B.; Wang, X. X.; Shao, K. P.; Zhu, X. G.; Liu, H. M. Eur. J. Med. Chem. 2015, 93, 321–329. DOI: 10.1016/j.ejmech.2015.02.026.
   PubMed Web of Science ®Google Scholar
• Harkov, S.; Havrylyuk, D.; Lesyk, R. CHCHT. 2013, 7, 381–389. DOI: 10.23939/chcht07.04.381.
   Google Scholar
• Al-Suwaidan, I. A.; Alanazi, A. M.; Alaa, A. M.; Mohamed, M. A.; El-Azab, A. S. Bioorg. Med. Chem. Lett. 2013, 23, 3935–3941. DOI: 10.1016/j.bmcl.2013.04.056.
   PubMed Web of Science ®Google Scholar
• Parikh, K.; Joshi, D. Med. Chem. Res. 2013, 22, 3688–3697. DOI: 10.1007/s00044-012-0369-3.
   Web of Science ®Google Scholar
• Awad, I. M.; Abdel-Rahman, A. E.; Bakhite, E. A. Phosphorus Sulfur Silicon Relat. Elem. 1991, 57, 293–301. DOI: 10.1080/10426509108038862.
   Web of Science ®Google Scholar
• Singh, D. C. P.; Hashim, S. R.; Singhal, R. G. E-Journal Chem. 2011, 8, 635–642. DOI: 10.1155/2011/482831.
   Google Scholar
• Taha, N. M. H.; Boray, A. A. A.; Saleh, N. M.; Fouad, S. A. J. Appl. Sci. Res. 2013, 9, 3108–3117.
   Google Scholar
• Ghorab, M. M.; Ragab, F. A.; Heiba, H. I.; Agha, H. M. J. Basic Appl. Chem. 2011, 1, 8–14.
   Google Scholar
• Behbehani, H.; Ibrahim, H. M. Molecules. 2012, 17, 6362–6385. DOI: 10.3390/molecules17066362.
   PubMed Web of Science ®Google Scholar
• Abu-Melha, S. Applied Sciences. 2018, 8, 2128. DOI: 10.3390/app8112128.
   Google Scholar
• Mohamed, O. S.; Al-Taifi, E. A.; El-Emary, T. I.; Bakhite, E. A. G. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 1061–1082. DOI: 10.1080/10426500601096369.
   Web of Science ®Google Scholar
• Dyachenko, V. D. Russ. J. Gen. Chem. 2004, 74, 641–642. DOI: 10.1023/B:RUGC.0000031876.17660.b5.
   Web of Science ®Google Scholar
• Fadda, A.; Refat, H.; Zaki, M. Molecules. 2000, 5, 701–709. DOI: 10.3390/50500701.
   Web of Science ®Google Scholar