

Simple and straight forward synthesis of 2,4-disubstituted quinazolines in aqueous medium
Madhav Bandaru (1)





(1) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
(2) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
(3) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
(4) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
(5) Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India
(*) Corresponding Author
Received: 12 Sep 2011 | Revised: 12 Oct 2011 | Accepted: 13 Oct 2011 | Published: 30 Jun 2012 | Issue Date: June 2012
Abstract
Efficient synthesis of diverse quinazolines from readily available starting materials was achieved in aqueous medium via one-pot protocol. A number of 2,4-disubstituted quinazolines were prepared in moderate to good yields under mild and catalyst-free conditions. Neutral reaction conditions, easy work-up procedures with wide substrate scope and atom economy are the remarkable features of this method.
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.3.2.252-257.527
Links for Article
| | | | | | |
| | | | | | |
| | |
Related Articles
Article Metrics


Funding information
Council of Scientific and Industrial Research (CSIR), New Delhi, India
Citations
[1]. Subrahmanya Ishwar Bhat, U. K. Das, Darshak R. Trivedi
An Efficient Three-component, One-pot Synthesis of Quinazolines under Solvent-free and Catalyst-free Condition
Journal of Heterocyclic Chemistry 52(4), 1253, 2015
DOI: 10.1002/jhet.2220

[2]. Xinglin Ye, Zhihan Yuan, Yirong Zhou, Qin Yang, Yepeng Xie, Zhihong Deng, Yiyuan Peng
Nickel-catalyzed Kumada Cross-coupling Reaction for the Synthesis of 2,4-Diarylquinazolines
Journal of Heterocyclic Chemistry 53(6), 1956, 2016
DOI: 10.1002/jhet.2513

[3]. Wing Cheung, Raymond J. Patch, Mark R. Player
Silver(II) oxide-mediated synthesis of 2,4-diarylquinazolines
Tetrahedron Letters 59(24), 2368, 2018
DOI: 10.1016/j.tetlet.2018.05.019

[4]. Wei Gao, Chun Gong, Qin Yang, Jianjun Yuan, Linchu Xu, Yiyuan Peng
Rh(III)-catalyzed oxidative ortho-C–H alkylation of 2,4-diarylquinazoline with potassium alkyltrifluoroborates
Canadian Journal of Chemistry 95(10), 1052, 2017
DOI: 10.1139/cjc-2017-0258

[5]. Tanya Gupta, Ankit Rohilla, Ankita Pathak, Md Jawaid Akhtar, Md Rafi Haider, M. Shahar Yar
Current perspectives on quinazolines with potent biological activities: A review
Synthetic Communications 48(10), 1099, 2018
DOI: 10.1080/00397911.2018.1431282

References
[1]. Kung, P. P.; Casper, M. D.; Cook, K. L.; Lingardo, L. W.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, J. R.; Cook, P. D.; Ecker, D. J. J. Med. Chem. 1999, 42, 4705-4713
http://dx.doi.org/10.1021/jm9903500
PMid:10579832
[2]. Malamas, M. S.; Millen, J. J. Med. Chem. 1991, 34, 1492-1503
http://dx.doi.org/10.1021/jm00108a038
PMid:1901912
[3]. Hess, H. J.; Cronin, T. H.; Scriabine, A. J. Med. Chem. 1968, 11, 130-136.
http://dx.doi.org/10.1021/jm00307a028
PMid:5637156
[4]. Baek, D.; Park, Y.; Heo, H. I.; Lee, M.; Yang, Z.; Choi, M. Bioorg. Med. Chem. Lett. 1998, 8, 3287-3290.
http://dx.doi.org/10.1016/S0960-894X(98)00602-7
[5]. Webber, S. E.; Bleckman, T. M.; Attard, J.; Deal, J. G.; Kathardekar, V.; Welsh, K. M.; Webber, S.; Janson, C. A.; Matthews, D. A.; Smith, W. W. J. Med. Chem. 1993, 36, 733-746.
http://dx.doi.org/10.1021/jm00058a010
PMid:8459400
[6]. Chao, Q.; Deng, L.; Shih, H.; Leoni, L. M.; Genini, D.; Carson, D. A.; Cottam, H. B. J. Med. Chem. 1999, 42, 3860-3873.
http://dx.doi.org/10.1021/jm9805900
PMid:10508435
[7]. Witt, A.; Bergman, J. Curr. Org. Lett. 2003, 7, 659-677.
[8]. Michael, J. P. Nat. Prod. Rep. 2008, 25, 166-187.
http://dx.doi.org/10.1039/b612168n
PMid:18250901
[9]. Michael, J. P. Nat. Prod. Rep. 2007, 24, 223-246.
http://dx.doi.org/10.1039/b509528j
PMid:17268614
[10]. Doyle, L. A.; Ross, D. D. Oncogene 2003, 22, 7340-7358.
http://dx.doi.org/10.1038/sj.onc.1206938
PMid:14576842
[11]. Henderson, E. A.; Bavetsias, V.; Theti, D. S.; Wilson, S. C.; Clauss, R.; Jackman, A. L. Bioorg Med. Chem. 2006, 14, 5020-5042.
http://dx.doi.org/10.1016/j.bmc.2006.03.001
[12]. Baruah, B.; Dasu, K.; Vaitilingam, B.; Mamnoor, P.; Venkata, P. P.; Rajagopal, S.; Yeleswarapu, K. R. Bioorg. Med. Chem. 2004, 12, 1991-1994.
http://dx.doi.org/10.1016/j.bmc.2004.03.005
[13]. Sharma, V. M.; Prasanna, P.; Adi Seshu, K. V.; Renuka, B.; Rao, C. V. L.; Kumar, G. S.; Narasimhulu, C. P.; Rajagopalan, R. Bioorg. Med. Chem. Lett. 2002, 12, 2303-2307.
http://dx.doi.org/10.1016/S0960-894X(02)00431-6
[14]. Chien, T. -C.; Chen, C. -S.; Yu, F. -H.; Chern, J. -W. Chem. Pharm. Bull. 2004, 52, 1422-1426.
http://dx.doi.org/10.1248/cpb.52.1422
[15]. Herget, T.; Freitag, M.; Morbitzer, M.; Kupfer, R.; Stamminger, T.; Marschall, M. Antimicrob. Agents Chemother. 2004, 48, 4154-4162.
http://dx.doi.org/10.1128/AAC.48.11.4154-4162.2004
PMid:15504835 PMCid:525407
[16]. Waisser, K.; Gregor, J.; Dostal, H.; Kunes, J.; Kubicova, L.; Klimesova, V.; Kaustova, J. Farmaco 2001, 56, 803-807.
http://dx.doi.org/10.1016/S0014-827X(01)01134-X
[17]. Kunes, J.; Bazant, J.; Pour, M.; Waisser, K.; Slosarek, M.; Janota, J. Farmaco 2000, 55, 725-729.
http://dx.doi.org/10.1016/S0014-827X(00)00100-2
[18]. Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095.
http://dx.doi.org/10.1126/science.8066447
PMid:8066447
[19]. Klutchko, S. R.; Zhou, H.; Winters, R. T.; Tran, T. P.; Bridges, A. J.; Althaus, I. W.; Amato, D. M.; Elliott, W. L.; Ellis, P. A.; Meade, M. A.; Roberts, B. J.; Fry, D. W.; Gonzales, A. J.; Harvey, P. J.; Nelson, J. M.; Sherwood, V.; Han, H. -K.; Pace, G.; Smaill, J. B.; Denny, W. A.; Showalter, H. D. H. J. Med. Chem. 2006, 49, 1475-1485.
http://dx.doi.org/10.1021/jm050936o
PMid:16480284
[20]. Ple, P. A.; Green, T. P.; Hennequin, L. F.; Curwen, J.; Fennell, M.; Allen, J.; Brempt, C. L.; Costello, G. J. Med. Chem. 2004, 47, 871-887.
http://dx.doi.org/10.1021/jm030317k
PMid:14761189
[21]. Colotta, V.; Catarzi, D.; Varano, F.; Lenzi, O.; Filacchioni, G.; Costagli, C.; Galli, A.; Ghelardini, C.; Galeotti, N.; Gratteri, P.; Sgrignani, J.; Deflorian, F.; Moro, S. J. Med. Chem. 2006, 49, 6015-6026.
http://dx.doi.org/10.1021/jm0604880
PMid:17004715
[22]. Lewerenz, A.; Hentschel, S.; Vissiennon, Z.; Michael, S.; Nieber, K. Drug Dev. Res. 2003, 58, 420-427.
http://dx.doi.org/10.1002/ddr.10187
[23]. Malecki, N.; Carato, P.; Rigo, G.; Goossens, J. F.; Houssin, R.; Bailly, C.; Henichart, J. P. Bioorg. Med. Chem. 2004, 12, 641-647.
http://dx.doi.org/10.1016/j.bmc.2003.10.014
[24]. Roy, A. D.; Subramanian, A.; Roy, R. J. Org. Chem. 2006, 71, 382-385.
http://dx.doi.org/10.1021/jo0518912
PMid:16388665
[25]. Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. J. Org. Chem. 2005, 70, 6941-6943
http://dx.doi.org/10.1021/jo050450f
PMid:16095321
[26]. Shreder, K. R.; Wong, M. S.; Nomanbhoy, T.; Leventhal, P. S.; Fuller, S. R. Org. Lett. 2004, 6, 3715-3718.
http://dx.doi.org/10.1021/ol048656a
PMid:15469331
[27]. Wiklund, P.; Evans, M. R.; Bergman, J. J. Org. Chem. 2004, 69, 6371-6376.
http://dx.doi.org/10.1021/jo049169b
PMid:15357597
[28]. Costa, M.; Ca, N. D.; Gabriele, B.; Massera, C.; Salerno, G.; Soliani, M. J. Org. Chem. 2004, 69, 2469-2477.
http://dx.doi.org/10.1021/jo0357770
PMid:15049647
[29]. Liu, J. -F.; Ye, P.; Zhang, B.; Bi, G.; Sargent, K.; Yu, L.; Yohannes, D.; Baldino, C. M. J. Org. Chem. 2005, 70, 6339-6345.
http://dx.doi.org/10.1021/jo0508043
PMid:16050695
[30]. Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B. Org. Lett. 2004, 6, 4775-4778.
http://dx.doi.org/10.1021/ol047919y
PMid:15575683
[31]. Connolly, D. J.; Cusack, D.; O’Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153-10202.
http://dx.doi.org/10.1016/j.tet.2005.07.010
[32]. Cubillo, F. P.; Scott, J. S.; Walton, J. C. Chem. Commun. 2008, 44, 2935-2937.
http://dx.doi.org/10.1039/b803630f
PMid:18566730
[33]. Ferrini, S.; Ponticelli, F.; Taddei, M. Org. Lett. 2007, 9, 69-72.
http://dx.doi.org/10.1021/ol062540s
PMid:17192087
[34]. Zhang, J.; Yu, C.; Wang, S.; Wan, C.; Wang, Z. Chem. Commun. 2010, 46, 5244-5246.
http://dx.doi.org/10.1039/c002454f
PMid:20574559
[35]. Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841-2843.
http://dx.doi.org/10.1021/ol100954x
PMid:20481477
[36]. Sarma, R. and Prajapati, D. Green Chem. 2011, 13, 718-722.
http://dx.doi.org/10.1039/c0gc00838a
[37]. Dabiri, M.; Salehi, P. and Bahramnejad, M. Synth. comm. 2010, 21, 3214-3225.
[38]. Dabiri, M.; Salehi, P.; Bahramnejad, M. and Sherafat, F. J. Comb. Chem. 2010, 12, 638-642.
http://dx.doi.org/10.1021/cc100043z
PMid:20831263
[39]. Murthy, S. N.; Madhav, B.; Kumar, A. V.; Nageswar, Y. V. D.; Rao, K. R. Tetrahedron 2009, 65, 5251-5256.
http://dx.doi.org/10.1016/j.tet.2009.04.081
[40]. Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Helv. Chim. Acta. 2009, 92, 2118-2124.
http://dx.doi.org/10.1002/hlca.200900098
[41]. Madhav, B.; Murthy, S. N.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, 6025-6028.
http://dx.doi.org/10.1016/j.tetlet.2009.08.033
[42]. Madhav, B.; Murthy, S. N.; Rao, K. R.; Nageswar, Y. V. D. Helv. Chim. Acta. 2010, 93, 257-260.
http://dx.doi.org/10.1002/hlca.200900254
[43]. Murthy, S. N.; Madhav, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3649-3653.
http://dx.doi.org/10.1016/j.tetlet.2010.05.028
[44]. Murthy, S. N.; Madhav, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, 5009-5011.
http://dx.doi.org/10.1016/j.tetlet.2009.06.078
[45]. Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3938-3939.
http://dx.doi.org/10.1016/j.tetlet.2010.05.096
[46]. Zhang, J.; Zhu, D.; Yu, C.; Wan, C. and Wang, Z. Org. Lett. 2010, 12, 2841-2843.
http://dx.doi.org/10.1021/ol100954x
PMid:20481477
[47]. Karnakar, K.; Shankar, J.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D. Synlett. 2011, 8, 1089-1096.
[48]. Portela-Cubillo, F.; Walton, J. C.; Scott, J. S. Chem. Comm. 2008, 25, 2935-2937.
http://dx.doi.org/10.1039/b803630f
PMid:18566730
[49]. Sarma, R.; Prajapati, D. Green Chem. 2011, 13, 718-722.
http://dx.doi.org/10.1039/c0gc00838a
[50]. Ferrini, S.; Ponticelli, F.; Taddei, M. Org. Lett. 2007, 9, 69-72.
http://dx.doi.org/10.1021/ol062540s
PMid:17192087
[51]. Fernando, P. -C.; Scott, J. S.; Walton, J. C. J. Org. Chem. 2009, 74, 4934-4942.
http://dx.doi.org/10.1021/jo900629g
PMid:19449842
[52]. Alonso, R.; Caballero, A.; Campos, P. J.; Sampedro, D.; Rodriguez, Miguel A. Tetrahedron, 2010, 66, 4469-4473.
http://dx.doi.org/10.1016/j.tet.2010.04.082
[53]. Dabiri, M.; Bahramnejad, M.; Salehi, P. Synthetic Commun. 2010, 40, 3214-3225.
http://dx.doi.org/10.1080/00397910903395250
[54]. Zhang, J.; Yu, C.; Wang, S.; Wan, C.; Wang, Z. Chem. Comm. 2010, 46, 5244-5246.
http://dx.doi.org/10.1039/c002454f
PMid:20574559
Supporting information
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.3.2.252-257.527

















European Journal of Chemistry 2012, 3(2), 252-257 | doi: https://doi.org/10.5155/eurjchem.3.2.252-257.527 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2021 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.