Generic placeholder image

Letters in Organic Chemistry

Author(s): Gholamhassan Imanzadeh*, Roghayyeh Asgharzadeh and Zahra Soltanzadeh

DOI: 10.2174/1570178619666220127123822

DownloadDownload PDF Flyer Cite As
Green Synthesis of Acylhydrazides Involving a Heterocyclic Moiety using Terminal Dihaloalkanes in Organic Salt Media under Solvent-Free Conditions

Page: [1005 - 1012] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

This paper aimed at investigating the reaction of some acyl hydrazides with different terminal dibromoalkanes. This investigation revealed that acyl hydrazide by reacting with 1,4 and 1,5- dibromoalkanes in the presence of DABCO (1,4-diazabicyclo[2.2.2]octane) and TBAB (tetrabutylammonium bromide) underwent a facile intramolecular N2-double-alkylation to form pyrrolidine and piperidine ring derivatives under solvent-free conditions. Moreover, the alkylation of acyl hydrazide with 1,6-dibromohexane as a substrate produced the related N2-mono-alkylated derivatives under the same conditions. Interestingly, using K2CO3 as the base in this reaction for 1,6-dibromohexane led to acyl hydrazide containing an azepane ring. Surprisingly, direct alkylation of 4-nitrobenzohydrazide with 1,2-dibromoethane led to an oxadiazine ring derivative. The product yield was found to be 60- 85% in 6-12 h.

Keywords: Acyl hydrazide, dihaloalkane, heterocyclic compound, organic salt media, solvent-free conditions, medicinal chemistry.

Graphical Abstract

[1]
Campos, J.F.; Berteina-Raboin, S. Catalysts, 2020, 10, 429-502.
[http://dx.doi.org/10.3390/catal10040429]
[2]
Himaja, M.; Poppy, D.; Asif, K. IJRAP, 2011, 2, 1079-1086.
[3]
Onitsuka, S.; Jin, Y.Z.; Shaikh, A.C.; Furuno, H.; Inanaga, J. Molecules, 2012, 17(10), 11469-11483.
[http://dx.doi.org/10.3390/molecules171011469] [PMID: 23018922]
[4]
Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Bahramnejad, M. Tetrahedron Lett., 2006, 47, 6983-6986.
[http://dx.doi.org/10.1016/j.tetlet.2006.07.127]
[5]
Ould M’hamed, M. Synth. Commun., 2015, 45, 2511-2528.
[http://dx.doi.org/10.1080/00397911.2015.1058396]
[6]
Banaszak, E. Aza-π-déficientsd’Intérêt Biologique Potentiel., Université Henri Poincaré Nancy I: French, 2007.
[7]
Fernandez, X.; Kerverdo, S.; Dunach, E.; Lizzani-Cuvelier, L. Actual. Chim., 2002, 252, 4-14.
[8]
Kraft, P.; Bajgrowicz, J.A.; Denis, C.; Frater, G. Angew. Chem. Int. Ed., 2000, 39, 2980-3010.
[http://dx.doi.org/10.1002/1521-3773(20000901)39:17<2980:AID-ANIE2980>3.0.CO;2-#]
[9]
Fournier. J. Actual. Chim., 2006, 298, 43-53.
[10]
Cao, H.; Chang, V.; Hernandez, R.; Heagy, M.D. J. Org. Chem., 2005, 70(13), 4929-4934.
[http://dx.doi.org/10.1021/jo050157f] [PMID: 15960490]
[11]
Mustafa, A.; Hishmat, O.H. J. Am. Chem. Soc., 1957, 79, 2225-2230.
[http://dx.doi.org/10.1021/ja01566a052]
[12]
Alcázar, J.; Oehlrich, D. Future Med. Chem., 2010, 2(2), 169-176.
[http://dx.doi.org/10.4155/fmc.09.144] [PMID: 21426184]
[13]
Katritzky, A.R.; Rees, C.W. Comprehensive heterocyclic chemistry; Pergamon Press: New York, 1984.
[14]
Kummar, S.; Kinders, R.; Rubinstein, L.; Parchment, R.E.; Murgo, A.J.; Collins, J.; Pickeral, O.; Low, J.; Steinberg, S.M.; Gutierrez, M.; Yang, S.; Helman, L.; Wiltrout, R.; Tomaszewski, J.E.; Doroshow, J.H. Nat. Rev. Cancer, 2007, 7(2), 131-139.
[http://dx.doi.org/10.1038/nrc2066] [PMID: 17251919]
[15]
Mc Devitt, C.A.; Callaghan, R. Pharm. Thera, 2007, 113, 429-441.
[http://dx.doi.org/10.1016/j.pharmthera.2006.10.003]
[16]
Leroux, V.; Gresh, N.; Liu, W.Q.; Garbay, C.; Maigret, B. J. Mol. Struct. THEOCHEM, 2007, 806, 51-66.
[http://dx.doi.org/10.1016/j.theochem.2006.11.010]
[17]
Raboisson, P.; Desjarlais, R.L.; Reed, R.; Lattanze, J.; Chaikin, M.; Manthey, C.L.; Tomczuk, B.E.; Marugán, J.J. Eur. J. Med. Chem., 2007, 42(3), 334-343.
[http://dx.doi.org/10.1016/j.ejmech.2006.10.015] [PMID: 17184884]
[18]
McGinley, P.L.; Koh, J.T. J. Am. Chem. Soc., 2007, 129(13), 3822-3823.
[http://dx.doi.org/10.1021/ja0701154] [PMID: 17348658]
[19]
Li, S-X.; Tong, Y-P.; Xie, X-C.; Wang, Q-H.; Zhou, H-N.; Han, Y.; Zhang, Z-Y.; Gao, W.; Li, S-G.; Zhang, X.C.; Bi, R-C. J. Mol. Biol., 2007, 366(5), 1603-1614.
[http://dx.doi.org/10.1016/j.jmb.2006.12.027] [PMID: 17224163]
[20]
Xu, J.; Stevenson, J. J. Chem. Inf. Comput. Sci., 2000, 40(5), 1177-1187.
[http://dx.doi.org/10.1021/ci000026+] [PMID: 11045811]
[21]
Fyaz, I. J. Fluor. Chem., 2002, 118, 27-33.
[http://dx.doi.org/10.1016/S0022-1139(02)00201-4]
[22]
Litvinov, V.P. Russ. Chem. Rev., 2003, 72, 69-85.
[http://dx.doi.org/10.1070/RC2003v072n01ABEH000764]
[23]
Kim, J.S.; Rhee, H.K.; Park, H.J.; Lee, S.K.; Lee, C.O.; Park Choo, H.Y. Bioorg. Med. Chem., 2008, 16(8), 4545-4550.
[http://dx.doi.org/10.1016/j.bmc.2008.02.049] [PMID: 18321715]
[24]
Zhang, L.; Guan, L.P.; Sun, X.Y.; Wei, C.X.; Chai, K.Y.; Quan, Z.S. Chem. Biol. Drug Des., 2009, 73(3), 313-319.
[http://dx.doi.org/10.1111/j.1747-0285.2009.00776.x] [PMID: 19207467]
[25]
Ryu, C.K.; Park, R.E.; Ma, M.Y.; Nho, J.H. Bioorg. Med. Chem. Lett., 2007, 17(9), 2577-2580.
[http://dx.doi.org/10.1016/j.bmcl.2007.02.003] [PMID: 17320386]
[26]
Li, J.; Zhao, Y.F.; Yuan, X.Y.; Xu, J.X.; Gong, P. Molecules, 2006, 11(7), 574-582.
[http://dx.doi.org/10.3390/11070574] [PMID: 17971729]
[27]
Sinkkonen, J.; Ovcharenko, V.; Zelenin, K.N.; Bezhan, I.P.; Chakchir, B.A.; Al-Assar, F.; Pihlaja, K. Eur. J. Org. Chem., 2002, 2046-2053.
[http://dx.doi.org/10.1002/1099-0690(200207)2002:13<2046:AID-EJOC2046>3.0.CO;2-C]
[28]
Hoepping, A.; Diekers, M.; Deuther-Conrad, W.; Scheunemann, M.; Fischer, S.; Hiller, A.; Wegner, F.; Steinbach, J.; Brust, P. Bioorg. Med. Chem., 2008, 16(3), 1184-1194.
[http://dx.doi.org/10.1016/j.bmc.2007.10.079] [PMID: 18023192]
[29]
Wawer, I.; Pisklak, M.; Chilmonczyk, Z. J. Pharm. Biomed. Anal., 2005, 38(5), 865-870.
[http://dx.doi.org/10.1016/j.jpba.2005.01.046] [PMID: 16087048]
[30]
Taylor, R.D.; MacCoss, M.; Lawson, A.D.G. J. Med. Chem., 2014, 57(14), 5845-5859.
[http://dx.doi.org/10.1021/jm4017625] [PMID: 24471928]
[31]
Vitaku, E.; Smith, D.T.; Njardarson, J.T. J. Med. Chem., 2014, 57(24), 10257-10274.
[http://dx.doi.org/10.1021/jm501100b] [PMID: 25255204]
[32]
Koz’minykh, V.O. Pharm. Chem. J., 2006, 40, 8-17.
[http://dx.doi.org/10.1007/s11094-006-0048-0]
[33]
Kidwai, M.; Kumar, R.; Goel, Y. Gp. Met. Chem., 1997, 20, 367-372.
[34]
Kidwai, M.; Mishra, P.; Kumar, R.; Saxsena, R.K.; Gupta, R.; Bradoo, S. Monatsh. Chem., 1998, 129, 961-965.
[35]
Fuqiang, L.I.U.; Palmer, D.C.; Sorgi, K.L. Tetrahedron Lett., 2004, 45, 1877-1880.
[http://dx.doi.org/10.1016/j.tetlet.2004.01.015]
[36]
Saha, A.; Kumar, R.; Kumar, R.; Devakumar, C. Indian J. Chem., 2010, 49B, 526-531.
[37]
Shindy, H.A.; El-Maghraby, M.A.; Eissa, F.M. Dyes Pigm, 2006, 70, 110-116.
[http://dx.doi.org/10.1016/j.dyepig.2005.04.003]
[38]
Zyl, J.M.V.; Basson, K.; Uebel, R.A.; Watt, V.D. Biochem. Pharmacol., 1989, 38, 2357-2362.
[http://dx.doi.org/10.1016/0006-2952(89)90476-0] [PMID: 2502119]
[39]
Danilenco, G.I.; Rubalco, S.L.; Maksimov, Y.N.; Baklan, U.F.; Guzhova, S.V. Pharm. Chem. J., 2000, 34, 23-24.
[http://dx.doi.org/10.1007/BF02524553]
[40]
Kettle, A.J.; Gedye, C.A.; Hampton, M.B.; Winterbourn, C.C. Biochem. J., 1995, 308(Pt 2), 559-563.
[http://dx.doi.org/10.1042/bj3080559] [PMID: 7772042]
[41]
Maruani, A.; Lee, M.T.W.; Watkins, G.; Akhbar, A.R.; Baggs, H.; Shamsabadi, A.; Richards, D.A.; Chudasama, V. RSC Advances, 2016, 6, 3372-3376.
[http://dx.doi.org/10.1039/C5RA26842G]
[42]
Akhbar, A.R.; Chudasama, V.; Fitzmaurice, R.J.; Powell, L.; Caddick, S. Chem. Commun. (Camb.), 2014, 50(6), 743-746.
[http://dx.doi.org/10.1039/C3CC47967F] [PMID: 24292272]
[43]
Chudasama, V.; Ahern, J.M.; Fitzmaurice, R.J.; Caddick, S. Tetrahedron Lett., 2011, 52, 1067-1069.
[http://dx.doi.org/10.1016/j.tetlet.2010.12.083]
[44]
Kim, Y.J.; Lee, D. Org. Lett., 2004, 6(23), 4351-4353.
[http://dx.doi.org/10.1021/ol048136f] [PMID: 15524481]
[45]
Shamsabadi, A.; Chudasama, V. Org. Biomol. Chem., 2016, 15(1), 17-33.
[http://dx.doi.org/10.1039/C6OB02099B] [PMID: 27782283]
[46]
Gillis, B.T.; Kadunce, R.E. J. Org. Chem., 1967, 32(1), 91-94.
[http://dx.doi.org/10.1021/jo01277a023] [PMID: 6035704]
[47]
Ismailov, V.M.; Mamedov, I.A.; Yusubov, N.N. Russ. J. Org. Chem., 2004, 40, 284-285.
[http://dx.doi.org/10.1023/B:RUJO.0000034957.86085.c2]
[48]
T.M.. Ismailov, V.M.; Yusubov, N.N.; Moskva, V.V. Russ. J. Org. Chem., 2009, 45, 1862-1863.
[49]
Mobinikhaledi, A.; Foroughifar, N.; Ahmadi, B. Phosphorus Sulfur Silicon Relat. Elem., 2004, 179, 1769-1775.
[http://dx.doi.org/10.1080/10426500490466391]
[50]
Mobinikhaledi, A.; Foroughifar, N.; Ahmadi, B. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180, 339-345.
[http://dx.doi.org/10.1080/104265090508406]
[51]
Dongamanti, A.; Aamate, V.K.; Gundu, S.; Devulapally, M.G. Russ. J. Gen. Chem., 2016, 86, 1705-1710.
[http://dx.doi.org/10.1134/S1070363216070288]
[52]
Asami, M.; Miyairi, N.; Sasahara, Y.; Ichikawa, K.; Hosoda, N.; Ito, S. Tetrahedron, 2015, 71, 6796-6802.
[http://dx.doi.org/10.1016/j.tet.2015.07.031]
[53]
Asgharzadeh, R.; Imanzadeh, G.H.; Soltanzadeh, Z. Green Chem. Lett. Rev., 2017, 10, 80-87.
[http://dx.doi.org/10.1080/17518253.2017.1293177]
[54]
Soltanzadeh, Z. Imanzadeh, G.H.; Noroozi-Pesyan, N.; Şahin, E.; Hooshmand, H. Tetrahedron, 2016, 72, 1736-1741.
[http://dx.doi.org/10.1016/j.tet.2016.02.024]
[55]
Imanzadeh, G.; Kazemi, F.; Zamanloo, M.; Mansoori, Y. Ultrason. Sonochem., 2013, 20(2), 722-728.
[http://dx.doi.org/10.1016/j.ultsonch.2012.09.003] [PMID: 23084790]
[56]
Imanzadeh, G.H.; Zare, A.; Khalafinezhad, A.; Hasaninejad, A.A.R.; Parhami, A.J. Iran. Chem. Soc, 2007, 4, 467-475.
[http://dx.doi.org/10.1007/BF03247234]
[57]
Imanzadeh, G.; Ahmadi, F.; Zamanloo, M.; Mansoori, Y. Molecules, 2010, 15(10), 7353-7362.
[http://dx.doi.org/10.3390/molecules15107353] [PMID: 20966877]
[58]
Imanzadeh, G.H.; Soltanizadeh, Z.; Khodayari, A.; Zamanloo, M.; Mansoori, Y.; Salehzadeh, J. Chin. J. Chem., 2012, 30, 891-899.
[http://dx.doi.org/10.1002/cjoc.201100351]
[59]
Imanzadeh, G.H.; Banaei, A.; Fathi, T.; Soltanzadeh, Z. Green Chem. Lett. Rev., 2016, 10, 1-9.
[http://dx.doi.org/10.1080/17518253.2016.1250958]
[60]
Katritzky, A.R.; Fan, W.Q. J. Org. Chem., 1990, 55, 3205-3209.
[http://dx.doi.org/10.1021/jo00297a041]
[61]
Yeung, J.M.; Knaus, E.E. Eur. J. Med. Chem-. Chim. Ther., 1986, 21, 181-185.