
NaOH/PEG-400: An eloquent system for the synthesis of new thienyl benzo[b]1,4-diazepines
Main Article Content
Abstract
A simple and eloquent procedure for the synthesis of a new series of thienyl benzo[b]1,4-diazepines is reported. They were synthesized by the condensation of o-phenylenediamine (o-PDA) with distinct hetero chalcones using NaOH in polyethylene glycol (PEG-400) as green and alternative reaction solvent. The significances of this present method are shorter reaction time, easy work-up, high yields, and mild reaction conditions. Furthermore, this method is environment friendly and without use of an expensive catalyst. The all newly synthesized compounds are characterized by the spectroscopic methods.


Article Details
[1]. Mallinath, M. L. Der Pharma Chem. 2011, 3(2), 273-276.
[2]. Konda, S. G.; Shaikh, B. M.; Chavan, S. A.; Dawane, B. S. Chinese Chem. Lett. 2011, 22, 65-68.
https://doi.org/10.1016/j.cclet.2010.09.012
[3]. Naraboli, B. S.; Biradar, J. S. Int. J. Pharm. Pharm. Sci. 2017, 9(8), 128-138.
https://doi.org/10.22159/ijpps.2017v9i8.19725
[4]. Sandra, C. M.; Eduardo, C. C.; Simon, H. O.; Teresa, R. A.; Antonio, N. C.; Lijanova, I. V. Med. Chem. 2012, 12(6), 611-618.
https://doi.org/10.2174/187152012800617713
[5]. Henderson, E. A.; Alber, D. G.; Baxter, R. C.; Bithell, S. K.; Budworth, J.; Carter, M. C. J. Med. Chem. 2007, 50(7), 1685-1692.
https://doi.org/10.1021/jm060747l
[6]. Griffin, C. E.; Kaye, A. M.; Bueno, F. R.; Kaye, A. D. Ochsner. J. 2013, 13(2), 214-223.
[7]. Thakuria, H.; Pramanik, A.; Borah, B. M.; Das, G. Tetrahedron Lett. 2006, 47, 3135-3138.
https://doi.org/10.1016/j.tetlet.2006.02.137
[8]. Reddy, K. V. V.; Rao, P. S.; Ashok, D. Synth. Commun. 2000, 30, 1825-1836.
[9]. Gupta, R.; Kumar, M.; Gupta, V. Heterocyclic Chemistry of Five Membered Heterocycles, New York, 1999, 2. 416-426.
https://doi.org/10.1007/978-3-662-07757-3
[10]. Herbert, J. A. L.; Suschitzky, H. J. Chem. Soc., Perkin Trans. 1974, 1, 2657-2661.
https://doi.org/10.1039/p19740002657
[11]. Morales, H. R.; Bulbarela, A. Heterocycles 1986, 24, 135-139.
https://doi.org/10.3987/R-1986-01-0135
[12]. Jung, D. I.; Choi, T. W.; Kim, Y. Y.; Kim, I. S.; Park, Y. M.; Lee, Y. G.; Jung, D. H. Synth. Commun. 1999, 29, 1941-1951.
[13]. Yadav, J. S.; Reddy, B. V. S.; Eshwaraian, B.; Anuradha, K. Green Chem. 2002, 4, 592-594.
https://doi.org/10.1039/B206558B
[14]. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 2001, 42, 3193-3195.
https://doi.org/10.1016/S0040-4039(01)00413-0
[15]. Balakrishna, M. S.; Kaboundin, B. Tetrahedron Lett. 2001, 42, 1127-1129.
https://doi.org/10.1016/S0040-4039(00)02168-7
[16]. Pozarentzi, M.; Stephanidou, S. J. Tetrahedron Lett. 2002, 43, 1755-1758.
https://doi.org/10.1016/S0040-4039(02)00115-6
[17]. Ma, Y.; Zhang, Y. Synth. Commun. 2002, 32, 163-166.
[18]. Jarikote, D. V.; Siddique, S. A.; Rajagopal, R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron Lett. 2003, 44, 1835-1838.
https://doi.org/10.1016/S0040-4039(03)00096-0
[19]. Kodomari, M.; Noguchi, T.; Aoyama, T. Synth. Commun. 2004, 34, 1783-1790.
https://doi.org/10.1081/SCC-120034159
[20]. Sabitha, G. S.; Reddy, K. K.; Reddy, K. B.; Reddy, N. M.; Yadav, J. S. Adv. Synth. Catal. 2004, 346, 921-923.
https://doi.org/10.1002/adsc.200303196
[21]. Reddy, B. M.; Sreekanth, P. M.; Reddy, V. R. J. Mol. Cat A 2005, 225, 71-78.
https://doi.org/10.1016/j.molcata.2004.09.003
[22]. Kaboudin, B.; Navaee, K. Heterocycles 2001, 55(8), 1443-1446.
https://doi.org/10.3987/COM-01-9253
[23]. Yadav, J. S.; Reddy, B. V. S.; Praveenkumar, S.; Nagaiah, K.; Lingaiah, N.; Saiprasad, P. S. Synthesis 2004, 6, 901-904.
https://doi.org/10.1055/s-2004-816013
[24]. Chari, M. A.; Syamasundar, K. Cat. Commun. 2005, 6(1), 67-70.
https://doi.org/10.1016/j.catcom.2004.10.009
[25]. Hegedus, A.; Hell, Z.; Potor, A. Cat. Lett. 2005, 105, 229-232.
https://doi.org/10.1007/s10562-005-8695-4
[26]. Chen, J.; Spear, S. K.; Huddieston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64-82.
https://doi.org/10.1039/b413546f
[27]. Heldebrant, D.; Jessop, P. G. J. Am. Chem. Soc. 2003, 125, 5600-5601.
https://doi.org/10.1021/ja029131l
[28]. Chandrasekhar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. K. Org. Lett. 2002, 4, 4383-4399.
https://doi.org/10.1021/ol0266976
[29]. Jiang, R.; Kuang, Y. Q.; Sun, X. L.; Zhang, S. Y. Tetrahedron Asym. 2004, 15, 743-746.
https://doi.org/10.1016/j.tetasy.2004.01.011
[30]. Namboodiri, V. V.; Varma, R. S. Green Chem. 2001, 3, 146-148.
https://doi.org/10.1039/b102337n
[31]. Suryakiran, N.; Ramesh, D.; Venkateswarulu, Y. Green Chem. Lett. 2007, 1, 73-78.
https://doi.org/10.1080/17518250701771909
[32]. Kamal, A.; Reddy, D. R.; Rajendar, S. Tetrahedron Lett. 2005, 46, 7951-7953.
https://doi.org/10.1016/j.tetlet.2005.09.082
[33]. Kamble, V. T.; Dawane, B. S.; Chavan, S. A.; Bhosale, R. B. Aust. J. Chem. 2007, 60, 302-304.
https://doi.org/10.1071/CH06377
[34]. Das, B.; Krishnaiah, M.; Balasybramanyam, P.; Veeranjaneyulu, B.; Nanda, K. D. Tetrahedron Lett. 2008, 49, 2225-2227.
https://doi.org/10.1016/j.tetlet.2008.02.050
[35]. Konda, S. G.; Humne, V. T.; Lokhande, P. D. Green Chem. 2011, 13, 2354-2358.
https://doi.org/10.1039/c1gc15153c
[36]. Dawane, B. S.; Konda, S. G.; Bhosale, R. B.; Shaikh, B. M. Acta. Pharm. 2009, 59, 473-482.
https://doi.org/10.2478/v10007-009-0034-7
[37]. Dawane, B. S.; Konda, S. G.; Mandawad, G. G.; Shaikh, B. M. Eur. J. Med. Chem. 2010, 45, 387-392.
[38]. Konda, S. G. Eur. J. Chem. 2014, 5(4), 676-680.
https://doi.org/10.5155/eurjchem.5.4.676-680.1110
[39]. Konda, S. G. J. Adv. Chem. Sci. 2016, 2(3), 363-365.
[40]. Mandawad, G. G.; Chobe, S. S.; Yemul, O. S.; Dawane, B. S. J. Pharm Res. 2011, 4(10), 3360-3363.
Most read articles by the same author(s)
- Pradeep Lokhande, Kamal Hasanzadeh, Shankaraiah Guruvaiah Konda, A novel and efficient approach for the synthesis of new halo substituted 2-arylpyrazolo[4,3-c] coumarin derivatives , European Journal of Chemistry: Vol. 2 No. 2 (2011): June 2011
- Shankaraiah Guruvaiah Konda, PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines , European Journal of Chemistry: Vol. 5 No. 4 (2014): December 2014
See how this article has been cited at scite.ai
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Downloads
Metrics
License Terms
Copyright © 2025 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).