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Synthesis 2018; 50(02): 349-360
DOI: 10.1055/s-0036-1591487
DOI: 10.1055/s-0036-1591487
paper
Catalyst-Free Regioselective Nazarov Cyclization of Aryl Allenyl Ketones
We are grateful to the National Natural Science Foundation of China (21302169), the Natural Science Foundation of Zhejiang Province (LQ16B020001), the Science Foundation of Zhejiang Sci-Tech University (13062121-Y), and the Program for Innovative Research Team of Zhejiang Sci-Tech University (13060052-Y) for financial support.
Weitere Informationen
Publikationsverlauf
Received: 03. August 2017
Accepted after revision: 13. September 2017
Publikationsdatum:
09. Oktober 2017 (online)
Abstract
The catalyst-free Nazarov cyclization of aryl allenyl ketones under thermal condition is developed. Various densely functionalized 2,3-dihydroindanones or indenones are readily produced in moderate to excellent yields. Significantly, this procedure features high functional group tolerance and exclusive regioselectivity. The resulting substituted 2,3-dihydroindanones can be conveniently converted into valuable conjugated benzofulvene building blocks.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591487.
- Supporting Information
- CIF File
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References
- 1a Wenz DR. Read de Alaniz J. Eur. J. Org. Chem. 2015; 23
- 1b Vaidya T. Eisenberg R. Frontier AJ. ChemCatChem 2011; 3: 1531
- 1c Nakanishi WW. West FG. Curr. Opin. Drug Discov. Dev. 2009; 12: 732
- 1d Tius MA. Chem. Soc. Rev. 2014; 43: 2979
- 1e Frontier AJ. Collison C. Tetrahedron 2005; 61: 7577
- 1f Pellissier H. Tetrahedron 2005; 61: 6479
- 1g Tius MA. Eur. J. Org. Chem. 2005; 2193
- 2a Spencer WT. III. Vaidya T. Frontier AJ. Eur. J. Org. Chem. 2013; 3621
- 2b Zhu L. Xi Z.-G. Lv J. Luo S. Org. Lett. 2013; 15: 4496
- 2c Sudhakar G. Satish K. Chem. Eur. J. 2015; 21: 6475
- 3a Cardozo MG. Iimura Y. Sugimoto H. Yamanishi Y. Hopfinger AJ. J. Med. Chem. 1992; 35: 584
- 3b Kawazoe K. Yamamoto M. Takaishi Y. Honda G. Fujita T. Sezik E. Yesilada E. Phytochemistry 1999; 50: 493
- 3c Hanson JR. Nat. Prod. Rep. 2004; 21: 312
- 3d Kashyap M. Das D. Preet R. Mohapatra P. Satapathy SR. Siddharth S. Kundu CN. Guchhait SK. Bioorg. Med. Chem. Lett. 2012; 22: 2474
- 4a Banerjee M. Mukhopadhyay R. Achari B. Banerjee AK. Org. Lett. 2003; 5: 3931
- 4b Liang G. Xu Y. Seiple IB. Trauner D. J. Am. Chem. Soc. 2006; 128: 11022
- 4c Snyder SA. Zografos AL. Lin Y. Angew. Chem. Int. Ed. 2007; 46: 8186
- 4d Gao S. Wang Q. Chen C. J. Am. Chem. Soc. 2009; 131: 1410
- 4e Malona JA. Cariou K. Frontier AJ. J. Am. Chem. Soc. 2009; 131: 7560
- 5a Fradette RJ. Kang M. West FG. Angew. Chem. Int. Ed. 2017; 56: 6335
- 5b Daviesa J. Leonori D. Chem. Commun. 2014; 50: 15171
- 5c Bow WF. Basak AK. Jolit A. Vicic DA. Tius MA. Org. Lett. 2010; 12: 440
- 5d Rieder CJ. Winberg KJ. West FG. J. Am. Chem. Soc. 2009; 131: 7504
- 5e Kokubo M. Kobayashi S. Chem. Asian J. 2009; 4: 526
- 5f Banaag AR. Tius MA. J. Org. Chem. 2008; 73: 8133
- 6a Janka M. He W. Frontier AJ. Eisenberg R. J. Am. Chem. Soc. 2004; 126: 6864
- 6b Malona JA. Colbourne JM. Frontier AJ. Org. Lett. 2006; 8: 5661
- 6c He W. Herrick IR. Atesin TA. Caruana PA. Kellenberger CA. Frontier AJ. J. Am. Chem. Soc. 2008; 130: 1003
- 6d Vaidya T. Atesin AC. Herrick IR. Frontier AJ. Eisenberg R. Angew. Chem. Int. Ed. 2010; 49: 3363
- 7a Marcus AP. Lee AS. Davis RL. Tantillo DJ. Sarpong R. Angew. Chem. Int. Ed. 2008; 47: 6379
- 7b Jin T. Yamamoto Y. Org. Lett. 2008; 10: 3137
- 7c Xi Z.-G. Zhu L. Luo S. Cheng J.-P. J. Org. Chem. 2013; 78: 606
- 7d Nie J. Zhu H.-W. Cui H.-F. Hua M.-Q. Ma J.-A. Org. Lett. 2007; 9: 3053
- 8 Cai S. Xiao Z. Shi Y. Gao S. Chem. Eur. J. 2014; 20: 8677
- 9a Krause N. Winter C. Chem. Rev. 2011; 111: 1994
- 9b Ma S. Chem. Rev. 2005; 105: 2829
- 9c Modern Allene Chemistry . Krause N. Hashmi AS. K. Wiley-VCH; Weinheim: 2004
- 9d Marx VM. Burnell DJ. Org. Lett. 2009; 11: 1229
- 9e Marx VM. Burnell DJ. J. Am. Chem. Soc. 2010; 132: 1685
- 9f Marx VM. LeFort FM. Burnell JD. Adv. Synth. Catal. 2011; 353: 64
- 10 Nagao Y. Lee W.-S. Kim K. Chem. Lett. 1994; 389
- 11a Suzuki T. Ohwada T. Shudo K. J. Am. Chem. Soc. 1997; 119: 6774
- 11b Douelle F. Tal L. Greaney MF. Chem. Commun. 2005; 660
- 11c Hashmi AS. K. Bats JW. Choi J-H. Schwarz L. Tetrahedron Lett. 1998; 39: 7491
- 12a Green NJ. Willis AC. Sherburn MS. Angew. Chem. Int. Ed. 2016; 55: 9244
- 12b Martinelli C. Cardone A. Pinto V. Talamo MM. D’arienzo ML. Mesto E. Schingaro E. Scordari F. Naso F. Musio R. Farinola GM. Org. Lett. 2014; 16: 3424
- 13a Shi M. Shao L.-X. Lu J.-M. Wei Y. Mizuno K. Maeda H. Chem. Rev. 2010; 110: 5883
- 13b Yu L. Wu Y. Chen T. Pan Y. Xu Q. Org. Lett. 2013; 15: 144
- 13c Nakamura E. Yamago S. Acc. Chem. Res. 2002; 35: 867
- 13d Yu L. Liu M.-X. Chen F.-L. Xu Q. Org. Biomol. Chem. 2015; 13: 8379
- 13e Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev. 2014; 114: 7317
- 13f Miao M. Luo Y. Xu H. Chen Z. Xu J. Ren H. Org. Lett. 2016; 18: 4292
- 14 Miao M. Cao J. Zhang J. Huang X. Wu L. Org. Lett. 2012; 14: 2718
- 15 Dudnik AS. Sromek AW. Rubina M. Kim JT. Kel’in AV. Gevorgyan V. J. Am. Chem. Soc. 2008; 130: 1440
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