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-00000084.xml
Synthesis 2020; 52(08): 1231-1238
DOI: 10.1055/s-0039-1690693
DOI: 10.1055/s-0039-1690693
special topic
Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade
This project was supported by the Deutsche Forschungsgemeinschaft (BA 1372/19-1) and by the Technische Universität München (TUM) Graduate School.Further Information
Publication History
Received: 30 August 2019
Accepted after revision: 16 September 2019
Publication Date:
02 October 2019 (online)
Dedicated to Professor Mark Lautens on the occasion of his 60th birthday
Published as part of the Special Topic Domino C–H Functionalization Reaction/Cascade Catalysis
Abstract
Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl2(MeCN)2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31–68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690693.
- Supporting Information
Primary Data
- for this article are available online at https://doi.org/10.1055/s-0039-1690693 and can be cited using the following DOI: 10.4125/pd0108th.
- Primary Data
-
References
- 1a Sundberg RJ. Indoles . Academic Press; San Diego: 1996
- 1b Joule JA. In Science of Synthesis, Vol. 10. Thomas EJ. Thieme; Stuttgart: 2000: 361-652
- 1c Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
- 1d Tois J, Franzén R, Koskinen A. Tetrahedron 2003; 59: 5395
- 1e Platon M, Amardeil R, Djakovitch L, Hierso J.-C. Chem. Soc. Rev. 2012; 41: 3929
- 1f Inman M, Moody CJ. Chem. Sci. 2013; 4: 29
- 1g Gribble GW. Indole Ring Synthesis: From Natural Products to Drug Discovery. Wiley; Chichester: 2016
- 1h Mancuso R, Dalpozzo R. Catalysts 2018; 8: 458
- 2a Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
- 2b Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
- 2c Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
- 2d Bartoli G, Bencivenni G, Dalpozzo R. Chem. Soc. Rev. 2010; 39: 4449
- 2e Lebrasseur N, Larrosa I. Adv. Heterocycl. Chem. 2012; 105: 309
- 2f Dalpozzo R. Chem. Soc. Rev. 2015; 44: 742
- 2g Leitch JA, Bhonoah Y, Frost CG. ACS Catal. 2017; 7: 5618
- 2h Vorobyeva DV, Osipov SN. Synthesis 2018; 50: 227
- 2i Kalepu J, Gandeepan P, Ackermann L, Pilarski LT. Chem. Sci. 2018; 9: 4203
- 2j Sandtorv AH. Adv. Synth. Catal. 2018; 357: 2403
- 2k Le Bras J, Muzart J. Synthesis 2019; 51: 2871
- 3a Ye J, Lautens M. Nat. Chem. 2015; 7: 863
- 3b Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
- 3c Wang J, Dong G. Chem. Rev. 2019; 119: 7478
- 4a Jiao L, Bach T. J. Am. Chem. Soc. 2011; 133: 12990
- 4b Jiao L, Herdtweck E, Bach T. J. Am. Chem. Soc. 2012; 134: 14563
- 4c Potukuchi HK, Bach T. J. Org. Chem. 2013; 78: 12263
- 4d Jiao L, Bach T. Synthesis 2014; 46: 35
- 5 Recent review: Wegmann M, Henkel M, Bach T. Org. Biomol. Chem. 2018; 16: 5376
- 6a Haak E. Synlett 2019; 30: 245
- 6b Ciulla MG, Zimmermann S, Kumar K. Org. Biomol. Chem. 2019; 17: 413
- 7a Jeffery T. J. Chem. Soc., Chem. Commun. 1984; 1287
- 7b Jeffery T. Tetrahedron Lett. 1985; 26: 2667
- 8 Synthesis of [a]-indole derivatives by the cyclization method: Jiang C, Gao Y, Li J. CN 108003160, 2018
- 9 Ishikura M, Terashima M. Tetrahedron Lett. 1992; 33: 6849
- 10a Wender PA, Cooper CB. Tetrahedron 1986; 42: 2985
- 10b Chen HG, Hoechstetter C, Knochel P. Tetrahedron Lett. 1989; 30: 4795
- 11 Review: Monakhova N, Ryabova S, Makarov V. J. Heterocycl. Chem. 2016; 53: 685
- 12a Ziegler FE, Jeroncic LO. J. Org. Chem. 1991; 56: 3479
- 12b Artis DR, Cho I.-S, Jaime-Figueroa S, Muchowski JM. J. Org. Chem. 1994; 59: 2456
- 12c Caddick S, Aboutayab K, Jenkins K, West RI. J. Chem. Soc., Perkin Trans. 1 1996; 675
- 12d Venning AR. O, Bohan PT, Alexanian EJ. J. Am. Chem. Soc. 2015; 137: 3731
- 12e Kaldas SJ, Cannillo A, McCallum T, Barriault L. Org. Lett. 2015; 17: 2864
- 13a Noland WE, Xia G.-M, Gee KR, Konkel MJ, Whalstrom MJ, Condoluci JJ, Rieger DL. Tetrahedron 1996; 52: 4555
- 13b Youn SW, Pastine SJ, Sames D. Org. Lett. 2004; 6: 581
- 13c Loh CC. J, Raabe G, Enders D. Chem. Eur. J. 2012; 18: 13250
- 13d Wu Y, Peng X, Luo B, Wu F, Liu B, Song F, Huang P, Wen S. Org. Biomol. Chem. 2014; 12: 9777
- 13e El-Sayed MT, Mahmoud KA, Heinemann FW, Hilgeroth A. J. Heterocycl. Chem. 2017; 54: 714
- 13f Hansen CL, Ohm RG, Olsen LB, Ascic E, Tanner D, Nielsen TE. Org. Lett. 2016; 18: 5990
- 13g Chen S, Li Y, Ni P, Yang B, Huang H, Deng G.-J. J. Org. Chem. 2017; 82: 2935
- 13h Garayalde D, Rusconi G, Nevado C. Helv. Chim. Acta 2017; 100: e1600333
- 13i Wang W, Bai X, Jin S, Guo J, Zhao Y, Miao H, Zhu Y, Wang Q, Bu Z. Org. Lett. 2018; 20: 3451
- 13j Kaufmann J, Jäckel E, Haak E. Angew. Chem. Int. Ed. 2018; 57: 5908
- 13k Yang R.-Y, Sun J, Sun Q, Yan C.-G. J. Org. Chem. 2018; 83: 5909
- 13l Liu B, Li J, Hu P, Zhou X, Bai D, Li X. ACS Catal. 2018; 8: 9463
- 14 While our work was in progress a patent entitled ‘Method for synthesizing [b]-cyclized indole derivatives’ appeared in which some closely related annulation reactions (Table 1, entries 1–3) were disclosed: Jiang C, Li J, Gao Y. CN 108084082, 2018
- 15a Rice LM, Hertz E, Freed ME. J. Med. Chem. 1964; 7: 313
- 15b Robarge MJ, Bom DC, Tumey LN, Varga N, Gleason E, Silver D, Song J, Murphy SM, Ekema G, Doucette C, Hanniford D, Palmer M, Pawlowski G, Danzig J, Loftus M, Hunady K, Sherf BA, Mays RW, Stricker-Krongrad A, Brunden KR, Harrington JJ, Bennani YL. Bioorg. Med. Chem. Lett. 2005; 15: 1749
- 16 For a related cyclization, see: Wong CM, Vuong KQ, Gatus MR. D, Hua C, Bhadbhade M, Messerle BA. Organometallics 2012; 31: 7500
- 17 Review: Stempel E, Gaich T. Acc. Chem. Res. 2016; 49: 2390
- 18a Nguyen Q, Nguyen T, Driver TG. J. Am. Chem. Soc. 2013; 135: 620
- 18b Tong S, Xu Z, Mamboury M, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2015; 54: 11809
- 19 Clark RD, Muchowski JM, Fischer LE, Flippin LA, Repke DB, Souchet M. Synthesis 1991; 871
- 20 Recent review: Evano G, Theunissen C. Angew. Chem. Int. Ed. 2019; 58: 7558
- 21 Brice JL, Harang JE, Timokhin VI, Anastasi NR, Stahl SS. J. Am. Chem. Soc. 2005; 127: 2868
- 22 For a recent review on norbornene in organic synthesis, see: Li C, Liu L, Fu X, Huang J. Synthesis 2018; 50: 2799
- 23 Baldwin JE, Kruse LI. J. Chem. Soc., Chem. Commun. 1977; 233
- 24 Tsotinis A, Pandelis AA, Davidson K, Prashar A, Sugden D. J. Med. Chem. 2007; 50: 6436
- 25 Xu D.-Q, Wu J, Luo S.-P, Zhang J.-X, Wu J.-Y, Du X.-H, Xu Z.-Y. Green Chem. 2009; 11: 1239
- 26 Haag BA, Zhang Z.-G, Li J.-S, Knochel P. Angew. Chem. Int. Ed. 2010; 49: 9513
- 27 Lin Y, Ye J, Zhang W, Gao Y, Chen H. Adv. Synth. Catal. 2019; 361: 432
- 28 Novel heteroaryl-substituted acetone derivatives as inhibitors of phospholipase A2: Lehr M, Ludwig J. WO 2004069797, 2004
Selected reviews and monographs:
Selected reviews:
Reviews:
Recent reviews: