Synthesis of 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones under solvent free conditions using ionic liquid as a mild and efficient catalyst | European Journal of Chemistry

Default Image

PDF

Published: Dec 31, 2014

DOI: https://doi.org/10.5155/eurjchem.5.4.671-675.1071

Keywords:

Aldehyde, Ionic liquid, Anthranilamide, Choline chloride, Solvent free condition, 2, 3-Dihydroquinazoline4(1H)-ones

Section

Short Communication

Issue

Vol. 5 No. 4 (2014): December 2014

Dates

Received 2014-04-10
Accepted 2014-06-13
Published 2014-12-31

Obaiah Obaiah

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Nandeesh Nagalingaiah Kebbahalli

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Raghavendra Manchigaiah Goravanahalli

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Pavankumar Siddalingaiah Chottanahalli

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Rangappa Subbegowda Kanchugarakoppal

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Mantelingu Kempegowda

eMail

Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570006, India

Abstract

A simple, green and environmentally benign procedure has been developed for the synthesis of 2,3-dihydroquinazoline-4(1H)-ones in basic ionic liquid via the cyclocondensation of 2-amino benzamide with an aldehyde. This offers several advantages such as high yields, simple procedure, low cost, short reaction times, mild and solvent free condition.

This Abstract was viewed 1855 times |

Article PDF downloaded 904 times

How to Cite

(1)

Obaiah, O.; Kebbahalli, N. N.; Goravanahalli, R. M.; Chottanahalli, P. S.; Kanchugarakoppal, R. S.; Kempegowda, M. Synthesis of 2-Aryl Substituted 2,3-Dihydroquinazoline-4(1H)-Ones under Solvent Free Conditions Using Ionic Liquid As a Mild and Efficient Catalyst. Eur. J. Chem. 2014, 5, 671-675.

Share

Links for Article

Crossref - Scopus - Google - European PMC

Crossref

Scopus

Google Scholar

Europe PMC

References

[1]. Daniel, A.; Erlanson, R. S.; McDowell, T. J. Med. Chem. 2004, 47, 3463-3482.
http://dx.doi.org/10.1021/jm040031v

[2]. Hour, M. J.; Huang, L. J.; Kuo, S. C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K. H. J. Med. Chem. 2000, 43, 4479-4487.
http://dx.doi.org/10.1021/jm000151c

[3]. Birch, H. L.; Buckley, G. M.; Davies, N.; Dyke, H. J.; Frost, E. J.; Gilbert, P. J.; Hannah, D. R.; Haughan, A. F.; Madigan, M. J.; Morgan, T.; Pitt, W. R.; Ratcliffe, A. J.; Ray, N. C.; Richard, M. D.; Sharpe, A.; Taylor, A. J.; Whitworth, J. M.; Williams, S. C. Bioorg. Med. Chem. Lett. 2005, 15, 5335-5339.
http://dx.doi.org/10.1016/j.bmcl.2005.06.108

[4]. Bonola, G.; Da, R. P.; Magistretti, M. J.; Massarani, E.; Setnikar, I. J. Med. Chem. 1968, 11, 1136-1139.
http://dx.doi.org/10.1021/jm00312a007

[5]. Rexall Drug Co., U. S. Patent 3257397, 1966.

[6]. Okumura, K.; Oine, T.; Yamada, Y.; Hayashi, G.; Nakama, M. J. Med. Chem. 1968, 11, 348-351.
http://dx.doi.org/10.1021/jm00308a036

[7]. Cohen, E.; Klarberg, B.; Vaughan, J. R. J. Am. Chem. Soc. 1959, 81, 5508-5509.
http://dx.doi.org/10.1021/ja01529a062

[8]. Alagarsamy, V.; Solomon, V. R.; Murugan, M. Bioorg. Med. Chem. 2007, 15, 4009-4015.
http://dx.doi.org/10.1016/j.bmc.2007.04.001

[9]. Levin, J. I.; Chan, P. I.; Bailey, T.; Katocs, A. S.; Venkatesan, A. M. Bioorg. Med. Chem. Lett. 1994, 4, 1141-1146.
http://dx.doi.org/10.1016/S0960-894X(01)80244-4

[10]. Instituto De Angeli S. P. A. French Patent M. 1893, 1963.

[11]. Shulton Inc. U. S. Patent 3265697, 1966.

[12]. Hirose, N.; Kuriyama, S.; Sohda, S.; Sakaguchi, K.; Yamamoto, H. Chem. Pharm. Bull. 1973, 21, 1005-1013.
http://dx.doi.org/10.1248/cpb.21.1005

[13]. Mustazza, C.; Borioni, A.; Sestili, I.; Sbraccia, M.; Rodomonte, A.; Ferretti, R.; Giudice, M. R. D. Chem. Pharm. Bull. 2006, 54, 611-622.
http://dx.doi.org/10.1248/cpb.54.611

[14]. Hamel, E.; Lin, C. M.; Plowman, J.; Wang, H.; Lee, K.; Paull, K. D. Biochem. Pharmacol. 1996, 51, 53-59.
http://dx.doi.org/10.1016/0006-2952(95)02156-6

[15]. Liu, X. W.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Angew. Chem., Int. Ed. 2009, 48, 348-351.
http://dx.doi.org/10.1002/anie.200804675

[16]. Zhang, Z. H.; Lu, H. Y.; Yang, S. H.; Gao, J. W. J. Comb. Chem. 2010, 12, 643-646.
http://dx.doi.org/10.1021/cc100047j

[17]. Chinigo, G. M.; Paige, M.; Grindrod, S.; Hamel, E.; Dakshanamurthy, S.; Chruszcz, M.; Minor, W.; Milton, L.; Brown, M. L. J. Med. Chem. 2008, 51, 4620-4631.
http://dx.doi.org/10.1021/jm800271c

[18]. Rueping, M.; Antonchick, A. P.; Sugiono, E.; Grenader, K. Angew. Chem., Int. Ed. 2009, 48, 908-910
http://dx.doi.org/10.1002/anie.200804770

[19]. Chowdhury, S.; Mohan, R. S.; Scott, J. L. Tetrahedron 2007, 63, 2363-2389.
http://dx.doi.org/10.1016/j.tet.2006.11.001

[20]. Muzart, J. Adv. Synth. Catal. 2006, 348, 275-295.
http://dx.doi.org/10.1002/adsc.200505273

[21]. Jain, N.; Kumar, A.; Chauhan, S.; Chauhan, S. M. S. Tetrahedron 2005, 61, 1015-1060.
http://dx.doi.org/10.1016/j.tet.2004.10.070

[22]. Zhao, H.; Malhotra, S. V. Aldrichimica Acta 2002, 35(3), 75-83.
http://dx.doi.org/10.1016/S0003-2670(01)01543-4

[23]. Darvatkar, N. B.; Bhilare, S. V.; Deorukhkar, A. R.; Raut, D. G.; Salunkhe, M. M. Green Chem. Lett. Rev. 2010, 3, 301-306.
http://dx.doi.org/10.1080/17518253.2010.485581

[24]. Greaves, T. L.; Drummond, C. J. Chem. Rev. 2008, 108(1), 206-237.
http://dx.doi.org/10.1021/cr068040u

[25]. Zhao, G.; Jiang, T.; Gao, H.; Han, B.; Juang, J.; Sun, D. Green Chem. 2004, 6, 75-77.
http://dx.doi.org/10.1039/b309700p

[26]. Raghavendra, G. M.; Ramesha, A. B.; Revanna, C. N.; Nandeesh, K. N.; Mantelingu, K.; Rangappa, K. S. Tetrahedron Lett. 2011, 52, 5571-5574.
http://dx.doi.org/10.1016/j.tetlet.2011.08.037

[27]. Chandrappa, S.; Umashankara, M.; Vinaya, K.; Ananda Kumar, C. S. Rangappa, K. S. Tetrahedron Lett. 2012, 53, 2632-2635.
http://dx.doi.org/10.1016/j.tetlet.2012.03.052

[28]. Raghavendra, G. M.; Harsha, K. B.; Vinaya, K.; Mantelingu, K.; Rangappa, K. S. Synth. Commun. 2011, 41, 2296-2303.
http://dx.doi.org/10.1080/00397911.2010.502986

[29]. Raghavendra, G. M.; Ramesha, A. B.; Revanna, C. N.; Nandeesh, K. N.; Mantelingu, K.; Rangappa, K. S. Tetrahedron Lett. 2011, 52(43), 5571-5574.
http://dx.doi.org/10.1016/j.tetlet.2011.08.037

[30]. Revanna, C. N.; Raghavendra, G. M.; JeniferVijay, T. A.; Rangappa, K. S.; Badregowd, D. G.; Mantelingu, K. Chem. Lett. 2014, 43, 178-180.
http://dx.doi.org/10.1246/cl.130732

[31]. Ramesha, A. B.; Raghavendra, G. M.; Nandeesh, K. N.; Rangappa, K. S.; Mantelingu, K. Tetrahedron Lett. 2012, 54, 95-100.
http://dx.doi.org/10.1016/j.tetlet.2012.10.112

[32]. Jenifer Vijay, T. A.; Nandeesh, K. N.; Raghavendra, G. M.; Rangappa, K. S.; Mantelingu, K. Tetrahedron Lett. 2013, 54, 6533-6537.
http://dx.doi.org/10.1016/j.tetlet.2013.09.094

[33]. Nandeesh, K. N.; Raghavendra, G. M.; Revanna, C. N.; Jenifer Vijay, T. A.; Rangappa, K. S.; Mantelingu, K. Synth. Commun. 2014, 44, 1103-1110.
http://dx.doi.org/10.1080/00397911.2013.848368

Supporting Agencies

University Grants Commission, Government of India, The project vide No. F. No. 39-710-2011 (SR/dated 12-01-2010).

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

License Terms

License Terms

by-nc

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).