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Synlett 2013; 24(20): 2619-2623
DOI: 10.1055/s-0033-1339878
DOI: 10.1055/s-0033-1339878
synpacts
One-Pot Synthesis of Multiply Substituted Quinoline and Quinazoline Derivatives via [2+2+2] Cascade Annulation with Diaryliodonium Salts
Further Information
Publication History
Received: 10 June 2013
Accepted after revision: 04 September 2013
Publication Date:
14 October 2013 (online)
Abstract
An efficient and regioselective method to multisubstituted quinoline and quinazoline derivatives with diaryliodonium salts catalyzed by Cu(OTf)2 has been presented. The reaction proceeded via cascade annulation in the mode of [2+2+2] form. This novel strategy enables use of readily available materials and bears great flexibility on the substitution groups.
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References
- 1a Michael JP. Nat. Prod. Rep. 2008; 25: 166
- 1b Bax BD, Chan PF, Eggleston DS, Fosberry A, Gentry DR, Gorrec F, Giordano I, Hann MM, Hennessy A, Hibbs M, Huang J, Jones E, Jones J, Brown KK, Lewis CJ, May EW, Saunders MR, Singh OC, Spitzfaden E, Shen C, Shillings A, Theobald AJ, Wohlkonig A, Pearson ND, Gwynn MN. Nature (London) 2010; 466: 935
- 1c Rouffet M, de Oliveira CA. F, Udi Y, Agrawal A, Sagi I, McCammon JA, Cohen SM. J. Am. Chem. Soc. 2010; 132: 8232
- 1d Andrews S, Burgess SJ, Skaalrud D, Kelly JX, Peyton DH. J. Med. Chem. 2010; 53: 916
- 1e Lord AM, Mahon MF, Lloyd MD, Threadgill MD. J. Med. Chem. 2009; 52: 868
- 1f Behenna DC, Stockdill JL, Stoltz BM. Angew. Chem. 2008; 120: 2400
- 2a Bhalla V, Vij V, Kumar M, Sharma PR, Kaur T. Org. Lett. 2012; 14: 1012
- 2b Velusamy M, Chen CH, Wen YS, Lin JT, Lin CC, Lai CH, Chou PT. Organometallics 2010; 29: 3912
- 2c Li H, Jäkle F. Macromolecules 2009; 42: 3448
- 2d Kim JL, Shin IS, Kim H. J. Am. Chem. Soc. 2005; 127: 1614
- 3a Verhaeghe P, Azas N, Gasquet M, Hutter S, Ducros C, Laget M, Rault S, Rathelot P, Vanelle P. Bioorg. Med. Chem. Lett. 2008; 18: 396
- 3b Henderson EA, Bavetsias V, Theti DS, Wilson SC, Clauss R, Jackman AL. Bioorg. Med. Chem. 2006; 14: 5020
- 3c Chien TC, Chen CS, Yu FH, Chern JW. Chem. Pharm. Bull. 2004; 52: 1422
- 3d Herget T, Freitag M, Morbitzer M, Kupfer R, Stamminger T, Marschall M. Antimicrob. Agents Chemother. 2004; 48: 4154
- 4a Marco-Contelles J, Pérez-Mayoral E, Samadi A, Carreiras MC, Soriano E. Chem. Rev. 2009; 109: 2652
- 4b Cheng CC, Yan SJ. Org. React. 1982; 28: 37
- 4c Henze HR, Carroll DW. J. Am. Chem. Soc. 1954; 76: 4580
- 4d Reitsema RH. Chem. Rev. 1948; 43: 47
- 4e Bergstrom FW. Chem. Rev. 1944; 35: 77; particularly p. 153 and 156
- 4f Kulkarni A, Török B. Green Chem. 2010; 12: 875
- 4g Chanda T, Verma RK, Singh MS. Chem. Asian J. 2012; 7: 778
- 5a Besson T, Chosson E. Comb. Chem. High Throughput Screening 2007; 10: 903
- 5b Michael JP. Nat. Prod. Rep. 2003; 20: 476
- 5c Undheim K, Benneche T. Comprehensive Heterocyclic Chemistry. Vol. 6. Katritzky AR, Rees CW. Pergamon Press; Oxford: 1998: 613-748
- 5d Yan YZ, Wang ZY. Chem. Commun. 2011; 47: 9513
- 6a Huang J.-R, Dong L, Han B, Peng C, Chen Y.-C. Chem. Eur. J. 2012; 18: 8896
- 6b Yan Y, Zhang Y, Feng C, Zha Z, Wang Z. Angew. Chem. Int. Ed. 2012; 51: 8077
- 6c Jia X, Peng F, Qing C, Huo C, Wang X. Org. Lett. 2012; 14: 4030
- 6d Sang P, Xie Y, Zou J, Zhang Y. Org. Lett. 2012; 14: 3894
- 6e McGowan M, McAvoy AC. Z, Buchwald SL. Org. Lett. 2012; 14: 3800
- 6f Stone MT. Org. Lett. 2011; 13: 2326
- 6g Richter H, Mancheño OG. Org. Lett. 2011; 13: 6066
- 6h Wang C, Li S, Liu H, Jiang Y, Fu H. J. Org. Chem. 2010; 75: 7936
- 7a Yusubov MS, Maskaev AV, Zhdankin VV. ARKIVOC 2011; (i): 370
- 7b Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 7c Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 7d Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
- 7e Grushin VV. Chem. Soc. Rev. 2000; 29: 315
- 7f Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
- 8a Stang PJ, Zhdankin VV. J. Am. Chem. Soc. 1993; 115: 9808
- 8b Boldyrev AI, Zhdankin VV, Simons J, Stang PJ. J. Am. Chem. Soc. 1992; 114: 10569
- 9a Skucas E, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 9090
- 9b Bielawski M, Zhu M, Olofsson B. Adv. Synth. Catal. 2007; 349: 2610
- 9c Bielawski M, Olofsson B. Chem. Commun. 2007; 2521
- 9d Bielawski M, Olofsson B. Org. Synth. 2009; 86: 308
- 10a Castro S, Fernández JJ, Vicente R, Fañanás FJ, Rodríguez F. Chem. Commun. 2012; 48: 9089
- 10b Hickman AJ, Sanford MS. ACS Catal. 2011; 1: 170
- 10c Chen B, Hou XL, Li YX, Wu YD. J. Am. Chem. Soc. 2011; 133: 7668
- 10d Wagner AM, Sanford MS. Org. Lett. 2011; 13: 288
- 10e Xiao B, Fu Y, Xu J, Gong TJ, Dai JJ, Yi J, Liu L. J. Am. Chem. Soc. 2010; 132: 468
- 10f Deprez NR, Sanford MS. J. Am. Chem. Soc. 2009; 131: 11234
- 10g Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
- 10h Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
- 10i Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006; 128: 4972
- 11a Wang Y, Chen C, Peng J, Li M. Angew. Chem. Int. Ed. 2013; 52: 5323
- 11b Su X, Chen C, Wang Y, Chen JJ, Lou ZB, Li M. Chem. Commun. 2013; 49: 6752
- 12 Phipps RJ, McMurray L, Ritter S, Duong HA, Gaunt MJ. J. Am. Chem. Soc. 2012; 134: 10773
- 13 The reaction of N-arylnitrilium salts with alkenes to produce dihydro quinolinium salts was reported: Moustafa AH, Hitzler MG, Lutz M, Jochims JC. Tetrahedron 1997; 53: 62
- 14 Wang, Y.; Chen, C.; Zhang, S.; Lou, Z.; Su, X.; Wen, L.; Li, M. Org. Lett. 2013, 15, 4794.
Selected recent examples:
For reviews on diaryliodonium salts, see:
For selected recent examples, see: