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Synthesis 2015; 47(14): 2055-2062
DOI: 10.1055/s-0034-1380550
DOI: 10.1055/s-0034-1380550
paper
Synthesis of 4-(Dimethylamino)quinazoline via Direct Amination of Quinazolin-4(3H)-one Using N,N-Dimethylformamide as a Nitrogen Source at Room Temperature
Further Information
Publication History
Received: 17 January 2015
Accepted after revision: 18 March 2015
Publication Date:
22 April 2015 (online)
Abstract
An efficient direct amination of quinazolin-4(3H)-ones using N,N-dimethylformamide as a nitrogen source is described that affords the corresponding 4-(dimethylamino)quinazolines in high yields. This transformation proceeds through efficient 4-toluenesulfonyl chloride mediated C–OH bond activation at room temperature.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380550.
- Supporting Information
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References
- 1a Havera HJ, Vidrio HJ. J. Med. Chem. 1979; 22: 1548
- 1b Hori M, Iemura R, Hara H, Ozaki A, Sukamoto T, Ohtaka H. Chem. Pharm. Bull. 1990; 38: 681
- 1c Liverton NJ, Armstrong DJ, Claremon DA, Remy DC, Bardwin JJ, Lynch RJ, Zhang G, Gould RJ. Bioorg. Med. Chem. Lett. 1998; 8: 483
- 1d Kung PP, Casper MD, Cook KL, Wilson-Lingardo L, Risen LM, Vickers TA, Ranken R, Blyn LB, Wyatt JR, Cook PD, Ecker DJ. J. Med. Chem. 1999; 42: 4705
- 1e Chao Q, Deng L, Shih H, Leoni LM, Genini D, Carson DA, Cottam HB. J. Med. Chem. 1999; 42: 3860
- 1f Brunton SA, Stibbard JH. A, Rubin LL, Kruse LI, Guicherit OM, Boyd EA, Price S. J. Med. Chem. 2008; 51: 1108
- 2a Barlaam B, Ballard P, Bradbury RH, Ducray R, Germain H, Hickinson DM, Hudson K, Kettle JG, Klinowska T, Magnien F, Ogilvie DJ, Olivier A, Pearson SE, Scott JS, Suleman A, Trigwell CB, Vautier M, Whittaker RD, Wood R. Bioorg. Med. Chem. Lett. 2008; 18: 674
- 2b Smits RA, de Esch IJ. P, Zuiderveld OP, Broeker J, Sansuk K, Guaita E, Coruzzi G, Adami M, Haaksma E, Leurs R. J. Med. Chem. 2008; 51: 7855
- 2c Sirisoma N, Pervin A, Zhang H, Jiang SC, Willardsen JA, Anderson MB, Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX. J. Med. Chem. 2009; 52: 2341
- 2d Iino T, Sasaki Y, Bamba M, Mitsuya M, Ohno A, Kamata K, Hosaka H, Maruki H, Futamura M, Yoshimoto R, Ohyama S, Sasaki K, Chiba M, Ohtake N, Nagata Y, Eiki J, Nishimura T. Bioorg. Med. Chem. Lett. 2009; 19: 5531
- 3 Barker AJ, Gibson KH, Grundy W, Godfrey AA, Barlow JJ, Healy MP, Woodburn JR, Ashton SE, Curry BJ, Scarlett L, Henthorn L, Richards L. Bioorg. Med. Chem. Lett. 2001; 11: 1911
- 4a Zhang YD, Xu CL, Houghten RA, Yu YP. J. Comb. Chem. 2007; 9: 9
- 4b Wissner A, Floyd MB, Johnson BD, Fraser H, Ingalls C, Nittoli T, Dushin RG, Discafani C, Nilakantan R, Marini J, Ravi M, Cheung K, Tan XZ, Musto S, Annable T, Siegel MM, Loganzo F. J. Med. Chem. 2005; 48: 7560
- 4c Hennequin LF, Allen J, Breed J, Curwen J, Fennell M, Green TP, Brempt CL. V. D, Morgentin R, Norman RA, Olivier A, Otterbein L, Ple PA, Warin N, Costello G. J. Med. Chem. 2006; 49: 6465
- 5a Kumar R, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 1121 ; and references therein
- 5b Kang F.-A, Sui Z, Murray WV. J. Am. Chem. Soc. 2008; 130: 11300
- 5c Luo Y, Wu J. Tetrahedron Lett. 2009; 50: 2103
- 5d Luo Y, Wu J. Tetrahedron 2009; 65: 6810
- 5e Hu Y, Ding Q, Ye S, Peng Y, Wu J. Tetrahedron 2011; 67: 7258
- 5f Qiu G, Huang P, Yang Q, Lu H, Xu JS, Deng Z, Zhang M, Peng YY. Synthesis 2013; 45: 3131
- 6 Lockman JW, Klimova Y, Anderson MB, Willardsen JA. Synth. Commun. 2012; 42: 1715
- 7 Peng Y.-Y, Wen Y, Mao X, Qiu G. Tetrahedron Lett. 2009; 50: 2405
- 8 Peng Y, Qiu G, Yang Q, Yuan J, Deng Z. Synthesis 2012; 44: 1237
- 10a Kadish KM, Han BC, Franzen MM, Araullo-McAdams C. J. Am. Chem. Soc. 1990; 112: 8364
- 10b Agarwal A, Chauhan PM. S. Synth. Commun. 2004; 34: 2925
- 10c Watanabe T, Tanaka Y, Sekiya K, Akita Y, Ohta A. Synthesis 1980; 39
- 10d D’Amico JJ, Webster ST, Campbell RH, Twine CE. J. Org. Chem. 1965; 30: 3618
- 10e Čechová L, Jansa P, Šála M, Dračínský M, Holý A, Janeba Z. Tetrahedron 2011; 67: 866
- 10f Samadi A, Silva D, Chioua M, do Carmo Carreiras M, Marco-Contelles J. Synth. Commun. 2011; 41: 2859
- 10g Li Y, Xie Y, Zhang R, Jin K, Wang X, Duan C. J. Org. Chem. 2011; 76: 5444
- 10h Wang J, Hou J.-T, Wen J, Zhang J, Yu X.-Q. Chem. Commun. 2011; 47: 3652
- 11 Chen W.-X, Shao L.-X. J. Org. Chem. 2012; 77: 9236
- 12a Peng Y.-Y, Liu J, Lei X, Yin Z. Green Chem. 2010; 12: 1072
- 12b Ding Q, Cao B, Liu X, Zong Z, Peng Y.-Y. Green Chem. 2010; 12: 1607
- 12c Liu J.-B, Zhou H.-P, Peng Y.-Y. Tetrahedron Lett. 2014; 55: 2872
- 13 Kodimuthali A, Mungara A, Prasunamba PL, Pal M. J. Braz. Chem. Soc. 2010; 21: 1439
- 14 Zielinski W, Mazik M. Pol. J. Chem. 1994; 68: 489