NaOH/PEG-400: An eloquent system for the synthesis of new thienyl benzo[b]1,4-diazepines

Gajanan Gopinath Mandawad; Baseer Mubeen Shaikh; Santosh Subhash Chobe; Shankaraiah Guruvaiah Konda

doi:10.5155/eurjchem.11.4.276-279.2009

PDF

Published: Dec 31, 2020

DOI: https://doi.org/10.5155/eurjchem.11.4.276-279.2009

Keywords:

Chalcones, Green synthesis, NaOH/PEG-400, o-Phenylenediamine, Operational simplicity, Benzo[b]1, 4-diazepines

Section

Research Article

Issue

Vol. 11 No. 4 (2020): December 2020

Dates

Received 2020-07-19
Accepted 2020-08-18
Published 2020-12-31

Gajanan Gopinath Mandawad

Department of Chemistry, Maharashtra Udayagiri College, Udgir-413517, Maharashtra, India

http://orcid.org/0000-0002-5317-2637

Baseer Mubeen Shaikh

Department of Chemistry, Sir Sayyed College, Aurangabad-431001, Maharashtra, India

http://orcid.org/0000-0001-8073-3332

Santosh Subhash Chobe

Organic Research Laboratory, Loknete Vyankatrao Hirey College, Nashik-422003, Maharashtra, India

http://orcid.org/0000-0001-5522-2522

Shankaraiah Guruvaiah Konda

Department of Chemistry, Karamsibhai Jethabhai Somaiya College, Kopargaon-423601, Maharashtra, India

http://orcid.org/0000-0002-1939-6784

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.

This Abstract was viewed 1110 times |

Article PDF downloaded 588 times

How to Cite

(1)

Mandawad, G. G.; Shaikh, B. M.; Chobe, S. S.; Konda, S. G. NaOH/PEG-400:/An/Eloquent/System/for/the/Synthesis/of/New/Thienyl/benzo[b]1,4-Diazepines. Eur. J. Chem. 2020, 11, 276-279.

Links for Article

Crossref - Scopus - Google - European PMC

References

[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)

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

Copyright © 2024 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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics