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Synthesis 2015; 47(24): 3990-3996
DOI: 10.1055/s-0035-1560268
DOI: 10.1055/s-0035-1560268
paper
Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols
Further Information
Publication History
Received: 30 June 2015
Accepted after revision: 24 August 2015
Publication Date:
18 September 2015 (online)
Abstract
A metal-free, one-pot, iodine-mediated, microwave-assisted cyclization of 1-(1′-arylvinyl)-2-naphthols (ortho-vinylnaphthols) into 1-arylnaphthofurans is developed. The 1-arylnaphthofurans are isolated in good to excellent yields (65–90%) using two equivalents of iodine in acetonitrile. The reactions proceed via the formation of 1-(2-iodo-1-phenylvinyl)naphthalen-2-ols as intermediates. Overall, the protocol is convenient as the reactions occur smoothly without the requirement of a transition-metal catalyst.
Key words
iodine-mediated - microwave-assisted - hydroarylation - 1-arylnaphthofurans - one-pot reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560268.
- Supporting Information
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References and Notes
- 1 Both authors contributed equally to this work.
- 2 Srivastava V, Negi AS, Kumar JK, Faridi U, Sisodia BS, Darokar MP, Luqman S, Khanuja SP. S. Bioorg. Med. Chem. Lett. 2006; 16: 911
- 3 Wu S.-F, Chang F.-R, Wang S.-Y, Hwang T.-L, Lee C.-L, Chen S.-L, Wu C.-C, Wu Y.-C. J. Nat. Prod. 2011; 74: 989
- 4 Quillardet P, Boscus D, Touati E, Hofnung M. Mutat. Res. Fundam. Mol. Mech. Mutagen. 1998; 422: 237
- 5 Cho C.-H, Neuenswander B, Lushington GH, Larock RC. J. Comb. Chem. 2008; 10: 941
- 6 Ohemeng KA, Appollina MA, Nguyen VN, Schwender CF, Singer M, Steber M, Ansell J, Argentieri D, Hageman W. J. Med. Chem. 1994; 37: 3663
- 7a Zwergel C, Valente S, Salvato A, Xu Z, Talhi O, Mai A, Silva A, Altucci L, Kirsch G. MedChemComm 2013; 4: 1571
- 7b de Olive-ira AB, de Oliveira GG, Carazza F, Filho RB, Bacha CT. M, Bauer L, Silva Gde A. B. A, Siqueira NC. S. Tetrahedron Lett. 1978; 19: 2653
- 8a Arcadi A, Cacchi S, Del Rosario M, Fabrizi G, Marinelli F. J. Org. Chem. 1996; 61: 9280
- 8b Wang J.-R, Manabe K. J. Org. Chem. 2010; 75: 5340
- 8c Yamaguchi M, Katsumata H, Manabe K. J. Org. Chem. 2013; 78: 9270
- 8d Zhou R, Wang W, Jiang Z.-j, Wang K, Zheng X.-l, Fu H.-y, Chen H, Li R.-x. Chem. Commun. 2014; 50: 6023
- 8e Kundu NG, Pal M, Mahanty JS, De M. J. Chem. Soc., Perkin Trans. 1 1997; 2815
- 9a Chen W, Li P, Miao T, Meng L.-G, Wang L. Org. Biomol. Chem. 2013; 11: 420
- 9b Liu J, Chen W, Ji Y, Wang L. Adv. Synth. Catal. 2012; 354: 1585
- 9c Ji Y, Li P, Zhang X, Wang L. Org. Biomol. Chem. 2013; 11: 4095
- 10a Kim I, Choi J. Org. Biomol. Chem. 2009; 7: 2788
- 10b Kim I, Lee S.-H, Lee S. Tetrahedron Lett. 2008; 49: 6579
- 11 Yue D, Yao T, Larock RC. J. Org. Chem. 2005; 70: 10292
- 12 Schmidt D, Malakar CC, Beifuss U. Org. Lett. 2014; 16: 4862
- 13a Liu Z, Liu L, Shafiq Z, Wu Y.-C, Wang D, Chen Y.-J. Synthesis 2007; 1961
- 13b Xu X, Liu J, Liang L, Li H, Li Y. Adv. Synth. Catal. 2009; 351: 2599
- 14 Kumar T, Mobin SM, Namboothiri IN. N. Tetrahedron 2013; 69: 4964
- 15 Rao VK, Shelke GM, Tiwari R, Parang K, Kumar A. Org. Lett. 2013; 15: 2190
- 16a Wang S, Li P, Yu L, Wang L. Org. Lett. 2011; 13: 5968
- 16b Hu Y, Zhang Y, Yang Z, Fathi R. J. Org. Chem. 2002; 67: 2365
- 16c Kwiecień H, Witczak M, Kowalewska M, Augustyniak M. Chem. Heterocycl. Compd. 2010; 46: 20
- 17a Li W.-T, Nan W.-H, Luo Q.-L. RSC Adv. 2014; 4: 34774
- 17b Ghosh R, Stridfeldt E, Olofsson B. Chem. Eur. J. 2014; 20: 8888
- 18 Pan C, Yu J, Zhou Y, Wang Z, Zhou M.-M. Synlett 2006; 1657
- 19 Singh FV, Wirth T. Synthesis 2012; 44: 1171
- 20 Shellhamer DF, Davenport KJ, Forberg HK, Herrick MP, Jones RN, Rodriguez SJ, Sanabria S, Trager NN, Weiss RJ, Heasley VL, Boatz JA. J. Org. Chem. 2008; 73: 4532