Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(22): 3131-3136
DOI: 10.1055/s-0033-1339848
DOI: 10.1055/s-0033-1339848
paper
Synthesis of 4-Arylquinazolines by Arylation of Quinazolin-4-ones under Mild Conditions
Further Information
Publication History
Received: 05 June 2013
Accepted after revision: 25 August 2013
Publication Date:
23 September 2013 (online)
Abstract
An efficient route to 4-arylquinazolines via arylation of quinazolin-4-ones under mild condition is described. The reaction is carried out by the palladium-catalyzed coupling of quinazolin-4-ones with arylboronic acids in the presence of TsCl leading to 4-arylquinazolines in good to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Deng YJ, Zhou XL, Desmoulin SK, Wu JM, Cherian C, Hou ZJ, Matherly LH, Gangjee A. J. Med. Chem. 2009; 52: 2940
- 1b Kabri Y, Gellis A, Vanelle P. Green Chem. 2009; 11: 201
- 1c Chen K, Aowad AF, Adelstein SJ, Kassis AI. J. Med. Chem. 2007; 50: 663
- 1d Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
- 1e Dempcy RO, Skibo EB. Biochemistry 1991; 30: 8480
- 1f Calvert AH, Jones TR, Dady PJ, Grzelakowskasztabert B, Paine RM, Taylor GA, Harrap KR. Eur. J. Cancer 1980; 16: 713
- 2a Baruah B, Dasu K, Vaitilingam B, Mamnoor P, Venkata PP, Rajagopal S, Yeleswarapu KR. Bioorg. Med. Chem. 2004; 12: 1991
- 2b Sharma VM, Prasanna P, Seshu KV, Renuka B, Rao CV. L, Kumar GS, Narasimhulu CP, Babu PA, Puranik RC, Subramanyam D, Venkateswarlu A, Rajagopal S, Kumar KB, Rao CS, Mamidi NV, Deevi DS, Ajaykumar R, Rajagopalan R. Bioorg. Med. Chem. Lett. 2002; 12: 2303
- 2c Foster A, Coffrey HA, Morin MJ, Rastinejad F. Science 1999; 286: 2507
- 3a Henderson EA, Bavetsias V, Theti DS, Wilson SC, Clauss R, Jackman AL. Bioorg. Med. Chem. 2006; 14: 5020
- 3b Malecki N, Carato P, Rigo B, Goossens J.-F, Houssin R, Baillyc C, Hènichart J.-P. Bioorg. Med. Chem. 2004; 12: 641
- 3c 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
- 4a 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
- 4b Murai M, Sekiguchi K, Nishioka T, Miyoshi H. Biochemistry 2009; 48: 688
- 4c Chappie TA, Humphrey JM, Allen MP, Estep KG, Fox CB, Lebel LA, Liras S, Marr ES, Menniti FS, Pandit J, Schmidt CJ, Tu MH, Williams RD, Yang FV. J. Med. Chem. 2007; 50: 182
- 4d Yang S, Liu G, Song BA, Jin LH, Hu DY, Zhang SM. Chin. J. Org. Chem. 2006; 26: 1429 ; Chem. Abstr. 2007, 147, 301104
- 4e Kanuma K, Omodera K, Nishiguchi M, Funakoshi T, Chaki S, Semple G, Tran TA, Kramer B, Hsu D, Casper M, Thomsen B, Beeley N, Sekiguchi Y. Bioorg. Med. Chem. Lett. 2005; 15: 2565
- 4f Liu G, Song BA, Sang WJ, Yang S, Jin LH, Ding X. Chin. J. Org. Chem. 2004; 24: 1296 ; Chem. Abstr. 2004 , 142, 134667
- 4g Shreder KR, Wong MS, Nomanbhoy T, Leventhal PS, Fuller SR. Org. Lett. 2004; 6: 3715
- 4h Tobe M, Isobe Y, Tomizawa H, Nakasaki T, Takahashi H, Fukazawa T, Hayashi H. Bioorg. Med. Chem. 2003; 11: 383
- 4i Rewcastle GW, Denny WA, Bridges AJ, Zhou HR, Cody DR, Mcmichael A, Fry DW. J. Med. Chem. 1995; 38: 3482
- 4j Rachid Z, Brahimi F, Qiu QY, Williams C, Hartaley JM, Hartaley JA, Jean-Claude BJ. J. Med. Chem. 2007; 50: 2605
- 4k Gomtsyan A, Bayburt EK, Schmidt RG, Zheng GZ, Perner RJ, Didomenico S, Koenig JR, Turner S, Jinkerson T, Drizin I, Hannick SM, Macri BS, McDonald HA, Honore P, Wismer CT, Marsh KC, Wetter J, Stewar KD, Oie T, Jarvis MF, Surowy CS, Faltynek CR, Lee CH. J. Med. Chem. 2005; 48: 744
- 5a Liu G, Liu CP, Ji CN, Sun L, Wen QW. Chin. J. Org. Chem. 2008; 28: 525 ; Chem. Abstr. 2009, 150, 121577
- 5b Ma Y, Liu F, Yan K, Song BA, Yang BS, Hu DY, Jin LH, Xue W. Chin. J. Org. Chem. 2008; 28: 1268 ; Chem. Abstr. 2009, 150, 352066
- 5c Xu GF, Song BA, Bhadury PS, Yang S, Zhang PQ, Jin LH, Xue W, Hu DY, Lu P. Bioorg. Med. Chem. 2007; 15: 3768
- 6a Brown DJ. Quinazolines, In The Chemistry of Heterocyclic Compounds (Supplement I). Vol. 55. Wiley; New York: 1996
- 6b Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
- 6c Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
- 6d Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
- 6e Fan S, Yang J, Zhang X. Org. Lett. 2011; 13: 4374
- 6f Lockman JW, Klimova Y, Anderson MB, Willardsen JA. Synth. Commun. 2012; 42: 1715
- 7a Seijas JA, Vásquez-Tato MP, Martinez MM. Tetrahedron Lett. 2000; 41: 2215
- 7b Weber C, Bielik A, Szendrei GI, Greiner I. Tetrahedron Lett. 2002; 43: 2971
- 7c Shreder KR, Wong MS, Nomanbhoy T, Leventhal PS, Fuller SR. Org. Lett. 2004; 6: 3715
- 7d Costa M, Cai ND, Gabriele B, Massera C, Salerno G, Soliani M. J. Org. Chem. 2004; 69: 2469
- 7e Nakamura H, Onagi S. Tetrahedron Lett. 2006; 47: 2539
- 7f Roy AD, Subramanian A, Roy R. J. Org. Chem. 2006; 71: 382
- 7g Zhang YD, Xu CL, Houghten RA, Yu YP. J. Comb. Chem. 2007; 9: 9
- 7h Ferrini S, Ponticelli F, Taddei M. Org. Lett. 2007; 9: 69
- 7i Harden DB, Mokrosz MJ, Strekowski L. J. Org. Chem. 1988; 53: 4137
- 7j Rueping M, Ieawsuwan W. Synlett 2007; 247
- 7k Milhau L, Guiry PJ. Synlett 2011; 383
- 8a Wacharasindhu S, Bardhan S, Wan Z.-K, Tabei K, Mansour TS. J. Am. Chem. Soc. 2009; 131: 4174
- 8b Kang F.-A, Sui ZH, Murray WV. J. Am. Chem. Soc. 2008; 130: 11300
- 8c Wan ZK, Wacharasindhu S, Levins CG, Lin M, Tabei K, Mansour TS. J. Org. Chem. 2007; 72: 10194
- 8d Wan ZK, Wacharasindhu S, Binnun E, Mansour T. Org. Lett. 2006; 8: 2425
- 8e Kang F.-A, Lanter JC, Cai C, Sui Z, Murray WV. Chem. Commun. 2010; 46: 1347
- 8f Shi C, Aldrich CC. Org. Lett. 2010; 12: 2286
- 8g Kang F.-A, Kodah J, Guan Q, Li X, Murray WV. J. Org. Chem. 2005; 70: 1957
- 8h Kang F.-A, Sui Z, Murray WV. Eur. J. Org. Chem. 2009; 461
- 8i Mehta VP, Modha SG, Van der Eycken EV. J. Org. Chem. 2010; 75: 976
- 9 Kitano Y, Suzuki T, Kawahara E, Yamazaki T. Bioorg. Med. Chem. Lett. 2007; 17: 5863
- 10a Kumar R, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 1121 ; and references therein
- 10b Ackermann L, Pospech J, Potukuchi HK. Org. Lett. 2012; 14: 2146
- 10c Ackermann L, Mulzer M. Org. Lett. 2008; 10: 5043
- 11a Luo Y, Wu J. Tetrahedron Lett. 2009; 50: 2103
- 11b Wu J, Wang LS, Fathi R, Yang Z. Tetrahedron Lett. 2002; 43: 4395
- 11c Wu J, Zhang L, Xia HG. Tetrahedron Lett. 2006; 47: 1525
- 11d Wang ZY, Wu J. Tetrahedron 2008; 64: 1736
- 11e Wu J, Zhang L, Luo Y. Tetrahedron Lett. 2006; 47: 6747
- 11f Lakshman MK, Thomson PF, Nuqui MA, Hilmer JH, Sevova N, Boggess B. Org. Lett. 2002; 4: 1479
- 11g Lakshman MK, Gunda P, Pradhan P. J. Org. Chem. 2005; 70: 10329
- 12a Peng YY, Wen YF, Mao XC, Qiu GY. S. Tetrahedron Lett. 2009; 50: 2405
- 12b Peng YY, Qiu GY. S, Yang Q, Yuan JJ, Deng ZH. Synthesis 2012; 44: 1237
- 13 Zhang J, Zhu D, Yu C, Wan C, Wang Z. Org. Lett. 2010; 12: 2841
- 14 Han B, Wang C, Han R.-F, Yu W, Duan X, Fang R, Yang X. Chem. Commun. 2011; 47: 7818
- 15 Huang C, Fu Y, Fu H, Jiang Y, Zhao Y. Chem. Commun. 2008; 44: 6333
For examples, see:
For examples, see:
For examples of 4-aminoquinazolines, see:
For examples of 4-alkyl(aryl)thioquinazolines, see:
For recent reviews, see:
For examples, see:
For an excellent review on phosphonium coupling, see:
For selected examples, see:
For examples of TsCl as C–OH bond activator, see: