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 2013; 45(8): 1094-1098
DOI: 10.1055/s-0032-1316876
DOI: 10.1055/s-0032-1316876
paper
Domino o-Alkylation and Heteroarylation of Iodoarenes: One-Pot Synthesis of Benzocyclohepta[b]indoles
Further Information
Publication History
Received: 16 October 2012
Accepted after revision: 05 March 2013
Publication Date:
20 March 2013 (online)
Abstract
A new strategy for the synthesis of benzocyclohepta[b]indoles via a palladium-catalyzed/norbornene-mediated domino intermolecular alkylation/intramolecular heteroarylation of iodoarenes is devised. This approach provides a straightforward route to polycyclic nitrogen-containing heterocycles with fused seven-membered rings from readily accessible precursors.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Somei M, Yamada F. Nat. Prod. Rep. 2005; 22: 73
- 1b Payack JF, Vazquez E, Matty L, Kress MH, McNamara J. J. Org. Chem. 2005; 70: 175
- 1c Ertl P, Jelfs S, Muhlbacher J, Schuffenhauer A, Selzer P. J. Med. Chem. 2006; 49: 4568
- 1d Faust R, Garratt PJ, Jones R, Yeh L.-K. J. Med. Chem. 2000; 43: 1050
- 1e Gastpar R, Goldbrunner M, Marko D, von Angerer E. J. Med. Chem. 1998; 41: 4965
- 1f Kozikowski AP, Ma D, Brewer J, Sun S, Costa E, Romeo E, Guidotti A. J. Med. Chem. 1993; 36: 2908
- 1g Cacchi S, Fabrizi G. Chem. Rev. 2011; 111: 215
- 1h Bartoli G, Bencivenni G, Daipozzo R. Chem. Soc. Rev. 2010; 39: 4449
- 1i Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
- 2 Hajela K, Jha AK, Singh MM, Jain GK, Balapure AK, Dwivedy A, Agarwal B, Murthy PS. R. Patent WO 094833, 2005 ; Chem. Abstr. 2005, 143, 387009.
- 3 Singh US, Shankar R, Yadav GP, Kharkwal G, Dwivedi A, Keshri G, Singh MM, Moulik PR, Hajela K. Eur. J. Med. Chem. 2008; 43: 2149
- 4 Singh US, Shankar R, Kumar A, Trivedi R, Chattopadhyay N, Shakya N, Palne S, Gupta S, Hajela K. Bioorg. Med. Chem. 2008; 16: 8482
- 5a Robinson B. The Fisher Indole Synthesis . Wiley; New York: 1982
- 5b Hughes DL. Org. Prep. Proced. Int. 1993; 25: 607
- 6 Barolo SM, Lukach AE, Rossi RA. J. Org. Chem. 2003; 68: 280
- 7 Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
- 8 Yamuna E, Zeller M, Adero PO, Prasad KJ. R. ARKIVOC 2012; (vi): 326
- 9 Jafarpour F, Hazrati H. Adv. Synth. Catal. 2010; 352: 363
- 10a Chiusoli GP, Catellani M, Costa M, Motti E, Della Ca’ N, Maestri G. Coord. Chem. Rev. 2010; 254: 456
- 10b Martins A, Mariampillai B, Lautens M. Top. Curr. Chem. 2010; 292: 1
- 10c Sehnal P, Taylor RJ. K, Fairlamb IJ. S. Chem. Rev. 2010; 110: 824
- 10d Muniz K. Angew. Chem. Int. Ed. 2009; 48: 9412
- 10e Catellani M, Motti E, Della Ca’ N. Acc. Chem. Res. 2008; 41: 1512
- 10f Lautens M, Alberico D, Bressy C, Fang Y.-Q, Mariampillai B, Wilhelm T. Pure Appl. Chem. 2006; 78: 351
- 10g Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
- 11a Chai DI, Thansandote P, Lautens M. Chem. Eur. J. 2011; 17: 8175
- 11b Della Ca’ N, Maestri G, Catellani M. Chem. Eur. J. 2009; 15: 7850
- 11c Aureggi V, Davoust M, Gericke KM, Lautens M. Synlett 2009; 1004
- 11d Jafarpour F, Ashtiani PT. J. Org. Chem. 2009; 74: 1364
- 11e Laleu B, Lautens M. J. Org. Chem. 2008; 73: 9164
- 11f Blaszykowski C, Aktoudianakis E, Alberico D, Bressy C, Hulcoop DG, Jafarpour F, Joushaghani A, Laleu B, Lautens M. J. Org. Chem. 2008; 73: 1888
- 11g Martins A, Lautens M. J. Org. Chem. 2008; 73: 8705
- 11h Mitsudo K, Thansandote P, Wilhelm T, Mariampillai B, Lautens M. Org. Lett. 2006; 8: 3939
- 11i Blaszykowski C, Aktoudianakis E, Bressy C, Alberico D, Lautens M. Org. Lett. 2006; 8: 2043
- 11j Martins A, Alberico D, Lautens M. Org. Lett. 2006; 8: 4827
- 11k Jafarpour F, Lautens M. Org. Lett. 2006; 8: 3601
- 11l Bressy C, Alberico D, Lautens M. J. Am. Chem. Soc. 2005; 127: 13148
- 12a Catellani M. Top. Organomet. Chem. 2005; 14: 21
- 12b Tsuji J. Palladium Reagents and Catalysis-New Perspectives for the 21st Century. Wiley; New York: 2004: 409
- 12c Catellani M. Synlett 2003; 298
- 12d Catellani M In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E.-I, de Meijere A. Wiley; New York: 2002: 1479
- 12e Catellani M, Mealli C, Motti E, Paoli P, Perez-Carreno E, Pregosin PS. J. Am. Chem. Soc. 2002; 124: 4336
- 12f Catellani M, Frignani F, Rangoni A. Angew. Chem., Int. Ed. Engl. 1997; 36: 119
For selected examples of annulated indoles, see:
For some recent reviews of indoles, see:
For reviews on the Fisher indole synthesis, see:
For reviews on Catellani reaction, see:
For palladium-catalyzed/norbornene-mediated functionalization of heterocycles, see: