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-00000083.xml
Synlett 2019; 30(20): 2247-2252
DOI: 10.1055/s-0039-1690734
DOI: 10.1055/s-0039-1690734
letter
Silver-Mediated Intramolecular Friedel–Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b] indolines and 3-Arylindoles
This work was financially supported by a Grant-in-Aid for Young Scientists (B) (Grant No. 16K18849 for T. A.) from the Japan Society for the Promotion of Science (JSPS).Further Information
Publication History
Received: 25 September 2019
Accepted after revision: 15 October 2019
Publication Date:
05 November 2019 (online)
Abstract
We disclose a silver-mediated intramolecular Friedel–Crafts-type cyclization of 2-benzyloxy-3-bromoindolines to afford an untapped family of isochromeno[3,4-b]indolines and 3-arylindoles, in which deformylative arylation of 2-(4-methoxybenzyloxy)-3-bromoindolines is reported for the first time. The isochromeno[3,4-b]indolines can be readily transformed into other heterocyclic moieties.
Key words
Friedel–Crafts - cyclization - isochromeno[3,4-b]indolines - deformylative arylation - 3-arylindoles - silverSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690734.
- Supporting Information
-
References and Notes
- 1 Ryder S. WO 2010151799A2, 2010
- 2 Goldfarb DS. US 20090163545A1, 2009
- 3a Beniddir MA, Martin M.-T, Dau M.-ET. H, Grellier P, Rasoanaivo P, Guéritte F, Litaudon M. Org. Lett. 2012; 14: 4162
- 3b Beniddir MA, Martin M.-T, Dau M.-ET. H, Rasoanaivo P, Guéritte F, Litaudon M. Tetrahedron Lett. 2013; 54: 2115
- 4 Momose R, Tanaka N, Fromont J, Kobayashi J. Org. Lett. 2013; 15: 2010
- 5a Kam T.-S, Tan S.-J, Ng S.-W, Komiyama K. Org. Lett. 2008; 10: 3749
- 5b Hirasawa Y, Arai H, Rahman A, Kusumawati I, Zaini NC, Shirota O, Morita H. Tetrahedron 2013; 69: 10869
- 6a Abramovitch RA, Hey DH. J. Chem. Soc. 1954; 1697
- 6b Eiden F, Dobinsky H. Synthesis 1970; 365
- 6c Engqvist R, Bergman J. Tetrahedron 2003; 59: 9649
- 6d Loewe W, Witzel S, Tappmeyer S, Albuschat R. J. Heterocycl. Chem. 2004; 41: 317
- 6e Peng W, Switalska M, Wang L, Mei Z.-W, Edazawa Y, Pang C.-Q, El-Sayed IE, Wietrzyk J, Inokuchi T. Eur. J. Med. Chem. 2012; 58: 441
- 6f Beaud R, Guillot R, Kouklovsky C, Vincent G. Angew. Chem. Int. Ed. 2012; 51: 12546
- 6g Gráczol-Fördös EE, Novák T, Blaskó G, Fejes I, Perron-Siera F, Nyerges M. Heterocycles 2013; 87: 2053
- 6h Deb ML, Pegu CD, Deka B, Dutta P, Kotmale AS, Baruah PK. Eur. J. Org. Chem. 2016; 3441
- 6i Liu J, Liu N, Yue Y, Wang Y, Chen K, Zhang J, Zhao S, Zhuo K. Chem. Asian J. 2017; 12: 401
- 6j Challa C, Ravindran J, Konai MM, Varughese S, Jacob J, Kumar BS. D, Halder J, Lankalapalli RS. ACS Omega 2017; 2: 5187
- 6k Abe T, Haruyama T, Yamada K. Synthesis 2017; 49: 4141
- 6l Miao C.-B, Sun Y.-F, Wu H, Sun X.-Q, Yang H.-T. Adv. Synth. Catal. 2018; 360: 2440
- 6m Rong G.-Q, Zhao J.-Q, Zhang X.-M, Xu X.-Y, Yuan W.-C, Zhou M.-Q. Tetrahedron 2018; 74: 2383
- 7 For a review on 3-arylated indoline, see: Denizot N, Tomakinson T, Beaud R, Kouklovsky C, Vincent G. Tetrahedron 2015; 56: 4413
- 8a The structure of voacalgine A was revised by Vincent and co-workers, see: Lachkar D, Denizot N, Bernadat G, Ahamada K, Beniddir MA, Dumontet V, Gallard J.-F, Guillot R, Leblanc K, N’nang EO, Turpin V, Kouklovsky C, Poupon E, Evanno L, Vincent G. Nat. Chem. 2017; 9: 793
- 8b Denizot N, Lachkar D, Kouklovsky C, Poupon E, Evanno L, Vincent G. Synthesis 2018; 50: 4229
- 9 Ye J, Lin Y, Liu Q, Xu D, Wu F, Liu B, Gao Y, Chen H. Org. Lett. 2018; 20: 5457
- 10a Abe T, Yamada K. Org. Lett. 2016; 18: 6504
- 10b Abe T, Yamada K. J. Nat. Prod. 2017; 80: 241
- 10c Abe T, Takahashi Y, Matsubara Y, Yamada K. Org. Chem. Front. 2017; 4: 2124
- 10d Abe T, Suzuki T, Anada M, Matsunaga S, Yamada K. Org. Lett. 2017; 19: 4275
- 10e Abe T, Yamada K. Org. Lett. 2018; 20: 1469
- 10f Abe T, Shimizu H, Takada S, Tanaka T, Yoshikawa M, Yamada K. Org. Lett. 2018; 20: 1589
- 10g Abe T, Satake S, Yamada K. Heterocycles 2019; 99: 379
- 10h Itoh T, Chiba Y, Kawaguchi S, Koitaya Y, Yoneta Y, Yamada K, Abe T. RSC Adv. 2019; 9: 10420
- 10i Abe T, Aoyama S, Ohmura M, Taniguchi M, Yamada K. Org. Lett. 2019; 21: 3367
- 11 Abe T, Kosaka Y, Asano M, Harasawa N, Mishina A, Nagasue M, Sugimoto Y, Katakawa K, Sueki S, Anada M, Yamada K. Org. Lett. 2019; 21: 826
- 12a Kim J, Movassaghi M. J. Am. Chem. Soc. 2011; 133: 14940
- 12b Boyer N, Movassaghi M. Chem. Sci. 2012; 3: 1798
- 12c Boyer N, Morrison KC, Kim J, Hergenrother PJ, Movassaghi M. Chem. Sci. 2013; 4: 1646
- 12d Coste A, Kim J, Adams TC, Movassaghi M. Chem. Sci. 2013; 4: 3191
- 12e Adams TC, Payette JN, Cheah JH, Movassaghi M. Org. Lett. 2015; 17: 4268
- 12f Loach RP, Fenton OS, Movassaghi M. J. Am. Chem. Soc. 2016; 138: 1057
- 13 Wang Y, Kong C, Du Y, Song H, Zhang D, Qin Y. Org. Biomol. Chem. 2012; 10: 2793
- 14 Lei H, Wang L, Xu Z, Ye T. Org. Lett. 2017; 19: 5134
- 15a Denizot N, Pouilhés A, Cucca M, Beaud R, Guillot R, Kouklovsky C, Vincent G. Org. Lett. 2014; 16: 5752
- 15b Denizot N, Guillot R, Kouklovsky C, Vincent G. Chem. Eur. J. 2015; 21: 18953
- 16a Matsumoto K, Tokuyama H, Fukuyama T. Synlett 2007; 3137
- 16b Ueda H, Satoh H, Matsumoto K, Sugimoto K, Fukuyama T, Tokuyama H. Angew. Chem. Int. Ed. 2009; 48: 7600
- 16c Satoh H, Ojima K, Ueda H, Tokuyama H. Angew. Chem. Int. Ed. 2016; 55: 15157
- 16d Sato S, Hirama A, Ueda H, Tokuyama H. Asian J. Org. Chem. 2017; 6: 54
- 16e Sato S, Hirama A, Adachi T, Kawauchi D, Ueda H, Tokuyama H. Heterocycles 2017; 94: 1940
- 16f Hakamata H, Sato S, Ueda H, Tokuyama H. Org. Lett. 2017; 19: 5308
- 16g Hakamata H, Ueda H, Tokuyama H. Org. Lett. 2019; 21: 4205
- 17a Hayashi M, Matsuura T, Tanaka I, Ohta H, Watanabe Y. Org. Lett. 2013; 15: 628
- 17b Rao ML. N, Ramakrishna BS. J. Org. Chem. 2019; 84: 5677
- 17c Guo L, Srimontree W, Zhu C, Maity B, Liu X, Cavallo L, Rueping M. Nat. Commun. 2019; 10: 1957
- 18a Rodíguez N, Goossen LJ. Chem. Soc. Rev. 2011; 40: 5030
- 18b Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
- 18c Gandeepan P, Müller T, Zell D, Cera G, Warrantz S, Ackermann L. Chem. Rev. 2019; 119: 2192
- 19a Goosen LJ, Deng G, Levy LM. Science 2006; 313: 662
- 19b Wang C, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
- 19c Chen L, Ju L, Bustin KA, Hoover JM. Chem. Commun. 2015; 51: 15059
- 19d Honevcutt AP, Hoover JM. ACS Catal. 2017; 7: 4597
- 20a Hu W, Guo Z, Yi X, Guo C, Chu F, Cheng G. Bioorg. Med. Chem. 2003; 11: 5539
- 20b Güzel Ö, Maresca A, Scozzafava A, Salman A, Balaban AT, Supuran CT. J. Med. Chem. 2009; 52: 4063
- 20c Richardson TI, Clarke CA, Yu K.-L, Yee YK, Bleisch TJ, Lopez JE, Jones SA, Hughes NE, Muehl BS, Lugar CW, Moore TL, Shetler PK, Zink RW, Osborne JJ, Montrose-Rafizadeh C, Patel N, Geiser AG, Galvin RJ. S, Dodge JA. ACS Med. Chem. Lett. 2011; 2: 148
- 20d El-Sayed NS, Shirazi AN, El-Meligy G, El-Ziaty AK, Rowley D, Sun J, Nagib ZA, Parang K. Tetrahedron Lett. 2014; 55: 1154
- 20e Gattu R, Bhattacharjee S, Mahato K, Khan AT. Org. Biomol. Chem. 2018; 16: 3760
- 21 Ham HW, Kimm BG, An HC, Kim DJ, Han JW, Kim GT, Lee HJ, Lim DW, Kim SH. A. WO 2014-KR11227, 2015
- 22 Li J, Bauer A, Di Mauro G, Maulide N. Angew. Chem. Int. Ed. 2019; 58: 9816
- 23 For an example of deformylation of 1,2-aminoalcohols, see: Liu X, Phan JH, Haugeberg BJ, Londhe SS, Clift MD. Beilstein J. Org. Chem. 2017; 13: 2895
For selected examples, see:
For recent reviews, see:
For selected examples, see:
Selected examples, see: