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Synthesis 2016; 48(22): 3976-3984
DOI: 10.1055/s-0035-1562504
DOI: 10.1055/s-0035-1562504
paper
Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
Weitere Informationen
Publikationsverlauf
Received: 04. April 2016
Accepted after revision: 26. Mai 2016
Publikationsdatum:
25. Juli 2016 (online)
Abstract
An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.
Key words
quinazoline - organoindium reagent - 4-tosyloxyquinazoline - 4-substituted quinazoline - cross-couplingSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562504.
- Supporting Information
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References
- 1a Hori M, Iemura R, Hara H, Ozaki A, Sukamoto T, Ohtaka H. Chem. Pharm. Bull. 1990; 38: 681
- 1b Michael JP. Nat. Prod. Rep. 2002; 19: 742
- 1c 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
- 1d Chen K, Al Aowad AF, Adelstein SJ, Kassis AI. J. Med. Chem. 2007; 50: 663
- 1e Brunton SA, Stibbard JH. A, Rubin LL, Kruse LI, Guicherit OM, Boyd EA, Price S. J. Med. Chem. 2008; 51: 1108
- 2a Michael JP. Nat. Prod. Rep. 1999; 16: 697
- 2b Michael JP. Nat. Prod. Rep. 2003; 20: 476
- 2c 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
- 3a Brown DJ. Quinazolines. In The Chemistry of Heterocyclic Compounds (Supplement I). Vol. 55. Wiley; New York: 1996
- 3b Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
- 3c Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
- 3d Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
- 3e Fan S, Yang J, Zhang X. Org. Lett. 2011; 13: 4374
- 4a 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
- 4b Zhang JT, Zhu DP, Yu CM, Wang CF, Wang ZY. Org. Lett. 2010; 12: 2841
- 4c 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
- 4d Murai M, Sekiguchi K, Nishioka T, Miyoshi H. Biochemistry 2009; 48: 688
- 4e Yang S, Liu G, Song BA, Jin LH, Hu DY, Zhang SM. Chin. J. Org. Chem. 2006; 26: 1429 ; (in Chinese)
- 4f 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
- 4g Liu G, Song BA, Sang WJ, Yang S, Jin LH, Ding X. Chin. J. Org. Chem. 2004; 24: 1296
- 4h Shreder KR, Wong MS, Nomanbhoy T, Leventhal PS, Fuller SR. Org. Lett. 2004; 6: 3715
- 4i Tobe M, Isobe Y, Tomizawa H, Nakasaki T, Takahashi H, Fukazawa T, Hayashi H. Bioorg. Med. Chem. 2003; 11: 383
- 4j Rewcastle GW, Denny WA, Bridges AJ, Zhou HR, Cody DR, McMichael A, Fry DW. J. Med. Chem. 1995; 38: 3482
- 4k Rachid Z, Brahimi F, Qiu QY, Williams C, Hartley JM, Hartley JA, Jean-Claude BJ. J. Med. Chem. 2007; 50: 2605
- 4l 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
- 4m Nakamura H, Onagi S. Tetrahedron Lett. 2006; 47: 2539
- 4n Wan ZK, Wacharasindhu S, Levins CG, Lin M, Tabei K, Mansour TS. J. Org. Chem. 2007; 72: 10194
- 4o Wan ZK, Wacharasindhu S, Binnun E, Mansour T. Org. Lett. 2006; 8: 2425
- 4p Peng YY, Qiu GY. S, Yang Q, Yuan JJ, Deng ZH. Synthesis 2012; 44: 1237
- 4q Zhao X, Zhou YR, Yang Q, Xie YP, Ding QP, Deng ZH, Zhang M, Xu JS, Peng YY. Synthesis 2013; 45: 3245
- 4r Chen X, Yang Q, Zhou YR, Deng ZH, Mao XC, Peng YY. Synthesis 2015; 47: 2055
- 5a Wacharasindhu S, Bardhan S, Wan Z.-K, Tabei K, Mansour TS. J. Am. Chem. Soc. 2009; 131: 4174
- 5b Connolly DJ, Lacey PM, McCarthy M, Saunders CP, Carroll A.-M, Goddard R, Guiry P. J. Org. Chem. 2004; 69: 6572
- 5c Lakshman MK, Thomson PF, Nuqui MA, Hilmer JH, Sevova N, Boggess B. Org. Lett. 2002; 4: 1479
- 5d Lakshman MK, Gunda P, Pradhan P. J. Org. Chem. 2005; 70: 10329
- 5e Qiu GY. S, Huang P, Yang Q, Lu H, Xu JS, Deng ZH, Zhang M, Peng YY. Synthesis 2013; 45: 3131
- 5f Peng YY, Huang P, Wang Y, Zhou YR, Yuan JJ, Yang Q, Jiang X, Deng ZH, Xu JS. Org. Biomol. Chem. 2014; 12: 5922
- 5g Ye XL, Yuan ZH, Zhou YR, Yang Q, Xie YP, Deng ZH, Peng YY. J. Heterocycl. Chem. 2016; in press
- 5h Ju J, Hua RM, Su J. Tetrahedron 2012; 68: 9364
- 5i Yan YZ, Wang ZY. Chem. Commun. 2011; 47: 9513
-
6a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 6b de Meijere A, Diederich F. Metal-Catalyzed Cross Coupling Reactions . 2nd ed. John Wiley & Sons; Weinheim: 2004
- 7a Shen ZL, Wang SY, Chok YK, Xu YH, Loh TP. Chem. Rev. 2013; 113: 271
- 7b Pena MA, Sestelo JP, Sarandeses LA. J. Org. Chem. 2007; 72: 1271
- 7c Xue Z, Yang DY, Wang CY. J. Organomet. Chem. 2006; 691: 247
- 7d Riveiros R, Rodriguez D, Sestelo JP, Sarandeses LA. Org. Lett. 2006; 8: 1403
- 7e Kim S, Seomoon D, Lee PH. Chem. Commun. 2009; 1873
- 7f Seomoon D, Lee K, Kim H, Lee PH. Chem. Eur. J. 2007; 13: 5197
- 7g Lee JY, Lee PH. J. Org. Chem. 2008; 73: 7413
- 7h Pérez I, Sestelo JP, Sarandeses LA. J. Am. Chem. Soc. 2001; 123: 4155
- 7i Lee PH, Lee SW, Lee K. Org. Lett. 2003; 5: 1103
- 7j Lee PH, Lee K, Kang Y. J. Am. Chem. Soc. 2006; 128: 1139
- 7k Zhao YS, Jin LQ, Li P, Lei A. J. Am. Chem. Soc. 2008; 130: 9429
- 7l Seomoon D, Lee K, Kim H, Lee PH. Chem. Eur. J. 2007; 13: 5197
- 7m Nomura R, Miyazaki SI, Matsuda H. J. Am. Chem. Soc. 1992; 114: 2738
- 7n Gao W, Luo Y, Ding QP, Peng YY, Wu J. Tetrahedron Lett. 2010; 51: 136
- 8a Lu H, Yang Q, Zhou YR, Guo YQ, Deng ZH, Ding QP, Peng YY. Org. Biomol. Chem. 2014; 12: 758
- 8b Zhang CY, Zhou YR, Deng ZH, Chen X, Peng YY. Eur. J. Org. Chem. 2015; 1735
- 8c Zhao Y, Liu WS, Li Q, Yang Q, Chai WB, Zeng MJ, Li RH, Peng YY. Bull. Environ. Contam. Toxicol. 2015; 94: 376
For selected examples, see: