Simple and straight forward synthesis of 2,4-disubstituted quinazolines in aqueous medium | European Journal of Chemistry

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Published: Jun 30, 2012

DOI: https://doi.org/10.5155/eurjchem.3.2.252-257.527

Keywords:

Catalyst free, Aqueous medium, One-pot synthesis, Ammonium acetate, 2-Amino carbonyl compounds, 2, 4-Disubstituted quinazolines

Section

Short Communication

Issue

Vol. 3 No. 2 (2012): June 2012

Dates

Received 2011-09-12
Accepted 2011-10-13
Published 2012-06-30

Madhav Bandaru

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Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

Narayana Murthy Sabbavarapu

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Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

Anil Kumar Bandam Santosh Pavan

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Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

Ashwan Kumar Akula

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Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

Nageswar Yadavalli Venkata Durga

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Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad, 500607, India

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.

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Bandaru, M.; Sabbavarapu, N. M.; Pavan, A. K. B. S.; Akula, A. K.; Durga, N. Y. V. Simple and Straight Forward Synthesis of 2,4-Disubstituted Quinazolines in Aqueous Medium. Eur. J. Chem. 2012, 3, 252-257.

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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 Agencies

Council of Scientific and Industrial Research (CSIR), New Delhi, India

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