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Synthesis 2013; 45(18): 2533-2544
DOI: 10.1055/s-0033-1338511
DOI: 10.1055/s-0033-1338511
paper
Synthesis of Aroylguanidines by an Unexpected Demethylation–Addition Cascade
Further Information
Publication History
Received: 06 May 2013
Accepted after revision: 30 June 2013
Publication Date:
01 August 2013 (online)
Abstract
A simple and efficient method was developed for the synthesis of N-aroyl-N′-arylguanidines under mild conditions by an unexpected demethylation–addition cascade reaction of readily available N-cyanoimidates with aryl amines. Moreover, 1-aryl-2-aminoquinazolin-4(1H)-ones and 2-(arylamino)quinazolin-4(3H)-ones can also be prepared by selective cyclization reactions of (2-fluorobenzoyl)- or (2-nitrobenzoyl)guanidines, respectively. This method provided two attractive strategies for the preparation 2-aminoquinazolinones derivatives from inexpensive reactants.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Masereel B, Pochet L, Laeckmann D. Eur. J. Med. Chem. 2003; 38: 547
- 2a Kehraus S, Gorzalka S, Hallmen C, Iqbal J, Müller CE, Wright AD, Wiese M, König GM. J. Med. Chem. 2004; 47: 2243
- 2b Wessels M, König GM, Wright AD. J. Nat. Prod. 2001; 64: 1556
- 2c Graziani EI, Andersen RJ. J. Nat. Prod. 1998; 61: 285
- 2d Tsukamoto S, Kato H, Hirota H, Fusetani N. Tetrahedron Lett. 1996; 37: 5555
- 2e Nozawa D, Takikawa H, Mori K. Bioorg. Med. Chem. Lett. 2001; 11: 1481
- 3a Ahmad S, Doweyko LM, Dugar S, Grazier N, Ngu K, Wu SC, Yost KJ, Chen B.-C, Gougoutas JZ, DiMarco JD, Lan S.-J, Gavin BJ, Chen AY, Dorso CR, Serafino R, Kirby M, Atwal KS. J. Med. Chem. 2001; 44: 3302
- 3b Lee S, Yi KY, Hwang SK, Lee BH, Yoo S, Lee K. J. Med. Chem. 2005; 48: 2882
- 3c Ahmad S, Ngu K, Combs DW, Wu SC, Weinstein DS, Liu W, Chen B.-C, Chandrasena G, Dorso CR, Kirby M, Atwal KS. Bioorg. Med. Chem. Lett. 2004; 14: 177
- 4a Peyman A, Scheunemann K.-H, Will DW, Knolle J, Wehner V, Breipohl G, Stilz HU, Carniato D, Ruxer J.-M, Gourvest J.-F, Auberval M, Doucet B, Baron R, Gaillard M, Gadek TR, Bodary S. Bioorg. Med. Chem. Lett. 2001; 11: 2011
- 4b Zhao Y, Bachelier R, Treilleux I, Pujuguet P, Peyruchaud O, Baron R, Clément-Lacroix P, Clézardin P. Cancer Res. 2007; 67: 5821
- 5 Adang AE. P, Lucas H, de Man AP. A, Engh RA, Grootenhuis PD. J. Bioorg. Med. Chem. Lett. 1998; 8: 3603
- 6a Ghorai P, Kraus A, Keller M, Gotte C, Igel P, Schneider E, Schnell D, Bernhardt G, Dove S, Zabel M, Elz S, Seifert R, Buschauer A. J. Med. Chem. 2008; 51: 7193
- 6b Birnkammer T, Spickenreither A, Brunskole I, Lopuch M, Kagermeier N, Bernhardt G, Dove S, Seifert R, Elz S, Buschauer A. J. Med. Chem. 2012; 55: 1147
- 7 Sorkin EM, Heel RC. Drugs 1986; 31: 301
- 8 Matthews H, Ranson M, Tyndall JD. A, Kelso MJ. Bioorg. Med. Chem. Lett. 2011; 21: 6760
- 9a Heel RC, Brogden RN, Speight TM, Avery GS. Drugs 1980; 20: 409
- 9b Scholz W, Albus U, Counillon L, Gögelein H, Lang H.-J, Linz W, Weichert A, Schölkens BA. Cardiovasc. Res. 1995; 29: 260
- 10 Zeymer U, Suryapranata H, Monassier JP, Opolski G, Davies J, Rasmanis G, Linssen G, Tebbe U, Schröder R, Tiemann R, Machnig T, Neuhaus K. J. Am. Coll. Cardiol. 2001; 38: 1644
- 11 Padmanabhan S, Lavin RC, Thakker PM, Guo J, Zhang L, Moore D, Perlman ME, Kirk C, Daly D, Burke-Howie KJ, Wolcott T, Chari S, Berlove D, Fischer JB, Holt WF, Durant GJ, McBurney RN. Bioorg. Med. Chem. Lett. 2001; 11: 3151
- 12 Carniato D, Gadek TR, Gourvest J.-F, Knolle J, Peyman A, Ruxer J.-M, Bodary SC. WO 0031046, 2000 ; Chem. Abstr. 2000, 133, 4997.
- 13a Baumgarth M, Beier N, Gericke R. J. Med. Chem. 1997; 40: 2017
- 13b Aihara K, Hisa H, Sato T, Yoneyama F, Sasamori J, Yamaguchi F, Yoneyama S, Mizuno Y, Takahashi A, Nagai A, Kimura T, Kogi K, Satoh S. Eur. J. Pharmacol. 2000; 404: 221
- 13c Andreadou I, Iliodromitis EK, Koufaki M, Kremastinos DT. Mini-Rev. Med. Chem. 2008; 8: 952
- 14 Bream JB, Picard CW. CH 518910, 1972 ; Chem. Abstr. 1972, 77, 61634.
- 15 Roudaut H, Traiffort E, Gorojankina T, Vincent L, Faure H, Schoenfelder A, Mann A, Manetti F, Solinas A, Taddei M, Ruat M. Mol. Pharmacol. 2011; 79: 453
- 16 Grigat E. DE 2020937, 1972 ; Chem. Abstr.; 1972, 76: 34266
- 17 Shi Y, Li C, O’Connor SP, Zhang J, Shi M, Bisaha SN, Wang Y, Sitkoff D, Pudzianowski AT, Huang C, Klei HE, Kish K, Yanchunas JJr, Liu EC.-K, Hartl KS, Seiler SM, Steinbacher TE, Schumacher WA, Atwal KS, Stein PD. Bioorg. Med. Chem. Lett. 2009; 19: 6882
- 18a Miyabe H, Matsumura A, Yoshida K, Yamauchi M, Takemoto Y. Lett. Org. Chem. 2004; 1: 119
- 18b Powell DA, Ramsden PD, Batey RA. J. Org. Chem. 2003; 68: 2300
- 18c Baker TJ, Tomioka M, Goodman M. Org. Synth. Coll. Vol. X . Wiley; London: 2004: 266
- 19 Groziak MP, Townsend LB. J. Org. Chem. 1986; 51: 1277
- 20 Debray J, Lévêque J, Philouze C, Draye M, Demeunynck M. J. Org. Chem. 2010; 75: 2092
- 21 Fray MJ, Mathias JP, Nichols CL, Po-Ba YM, Snow H. Tetrahedron Lett. 2006; 47: 6365
- 22 Citerio L, Rivera E, Saccarello M.-L, Stradi R, Gioia B. J. Heterocycl. Chem. 1980; 17: 97
- 23 Götz N, Zeeh B. Synthesis 1976; 268
- 24a Cunha S, Costa MB, Napolitano HB, Lariucciand C, Vencato I. Tetrahedron 2001; 57: 1671
- 24b Cunha S, de Lima BR, de Souza AR. Tetrahedron Lett. 2002; 43: 49
- 25 Hegarty AF, Hegarty CN, Scott FL. J. Chem. Soc., Perkin Trans. 2 1973; 2054
- 26a Lin P, Ganesan A. Tetrahedron Lett. 1998; 39: 9789
- 26b Dodd DS, Zhao Y. Tetrahedron Lett. 2001; 42: 1259
- 26c Ghosh AK, Hol WG. J, Fan E. J. Org. Chem. 2001; 66: 2161
- 26d Katritzky AR, Rogovoy BV, Cai X, Kirichenko N, Kovalenko KV. J. Org. Chem. 2004; 69: 309
- 27 Shinada T, Umezawa T, Ando T, Kozuma H, Ohfune Y. Tetrahedron Lett. 2006; 47: 1945
- 28 Yin P, Ma W.-B, Chen Y, Huang W.-C, Deng Y, He L. Org. Lett. 2009; 11: 5482
- 29a M’Hamed MO, M’Rabet H, Efrit ML. C. R. Chim. 2007; 10: 1147
- 29b Zarguil A, Boukhris S, El Efrit ML, Souizi A, Essassi EM. Tetrahedron Lett. 2008; 49: 5883
- 29c He RJ, Ching SM, Lam YL. J. Comb. Chem. 2006; 8: 923
- 29d Che J, Raghavendra MS, Lam YL. J. Comb. Chem. 2009; 11: 378
- 29e Huffman KR, Schaefer FC. J. Org. Chem. 1963; 28: 1816
- 30 Yin P, Liu N, Deng Y.-X, Chen Y, Deng Y, He L. J. Org. Chem. 2012; 77: 2649
- 31 DeRuiter J, Brubaker AN, Millen J, Riley TN. J. Med. Chem. 1986; 29: 627
- 32 Kulkarni A, Zhou W, Török B. Org. Lett. 2011; 13: 5124
- 33 Sahoo SK, Jamir L, Guin S, Patel BK. Adv. Synth. Catal. 2010; 352: 2538