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Synthesis 2012; 44(21): 3371-3377
DOI: 10.1055/s-0032-1316775
DOI: 10.1055/s-0032-1316775
paper
Access to Aromatic Ring-Fused Benzimidazoles Using Photochemical Substitutions of the Benzimidazol-2-yl Radical
Further Information
Publication History
Received: 26 July 2012
Accepted after revision: 20 August 2012
Publication Date:
31 August 2012 (online)
Abstract
Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.
Key words
cyclization - diazoles - heterocycles - nucleophilic aromatic substitution - radical reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1 Bowman WR, Storey JM. D. Chem. Soc. Rev. 2007; 36: 1803
- 2 Minisci F, Fontana F, Pianese G, Yan YM. J. Org. Chem. 1993; 58: 4207
- 3 Beckwith AL. J, Bowry VW, Bowman WR, Mann E, Parr J, Storey JM. D. Angew. Chem. Int. Ed. 2004; 43: 95 ; Angew. Chem. 2004, 116, 97
- 4 McLoughlin PT. F, Clyne MA, Aldabbagh F. Tetrahedron 2004; 60: 8065
- 5 Allin SM, Bowman WR, Elsegood MR. J, McKee V, Karim R, Rahman SS. Tetrahedron 2005; 61: 2689
- 6 Clyne MA, Aldabbagh F. Org. Biomol. Chem. 2006; 4: 268
- 7 Aldabbagh F, Clyne MA. Lett. Org. Chem. 2006; 3: 510
- 8 Bennasar M.-L, Roca T, Ferrando F. Org. Lett. 2006; 8: 561
- 9 Lynch M, Hehir S, Kavanagh P, Leech D, O’Shaughnessy J, Carty MP, Aldabbagh F. Chem.–Eur. J. 2007; 13: 3218
- 10 Allin SM, Barton WR. S, Bowman WR, Bridge E, Elsegood MR. J, McInally T, McKee V. Tetrahedron 2008; 64: 7745
- 11a Curran DP, Keller AI. J. Am. Chem. Soc. 2006; 128: 13706
- 11b Majumdar KC, Debnath P, Alam S, Islam R. J. Sulfur Chem. 2008; 29: 467
- 11c Bennasar M.-L, Roca T. J. Org. Chem. 2011; 76: 4213
- 11d Kostiuk SL, Woodcock T, Dudin LF, Howes PD, Harrowven DC. Chem.–Eur. J. 2011; 17: 10906
- 12 Fagan V, Bonham S, Carty MP, Aldabbagh F. Org. Biomol. Chem. 2010; 8: 3149
- 13 Fagan V, Bonham S, Carty MP, Saenz-Méndez P, Eriksson LA, Aldabbagh F. Bioorg. Med. Chem. 2012; 20: 3223
- 14 Allin SM, Bowman WR, Karim R, Rahman SS. Tetrahedron 2006; 62: 4306
- 15a de Figueiredo RM, Thoret S, Huet C, Dubois J. Synthesis 2007; 529
- 15b Laha JK, Cuny GD. J. Org. Chem. 2011; 76: 8477
- 16 Majumdar KC, Debnath P, Taher A, Pal AK. Can. J. Chem. 2008; 86: 325
- 17 Tholander J, Bergman J. Heterocycles 1999; 51: 1275
- 18 Park Y.-T, Jung C.-H, Kim M.-S, Kim K.-W, Song NW, Kim D. J. Org. Chem. 2001; 66: 2197
- 19a Dobbs AP, Jones K, Veal KT. Tetrahedron Lett. 1997; 38: 5379
- 19b Fiumana A, Jones K. Tetrahedron Lett. 2000; 41: 4209
- 20 Linsenmeier AM, Williams CM, Bräse S. J. Org. Chem. 2011; 76: 9127
- 21 Barton DH. R, Garcia B, Togo H, Zard SZ. Tetrahedron Lett. 1986; 27: 1327
- 22 Moriarty E, Carr M, Bonham S, Carty MP, Aldabbagh F. Eur. J. Med. Chem. 2010; 45: 3762
- 23 Aldabbagh F, Bowman WR. Tetrahedron 1999; 55: 4109
- 24 East JE, Kennedy AJ, Tomsig JL, De Leon AR, Lynch KR, Macdonald TL. Bioorg. Med. Chem. Lett. 2010; 20: 7132
- 25 Albanese D, Ghidoli C, Zenoni M. Org. Process Res. Dev. 2008; 12: 736
- 26 Hubbard JW, Piegols AM, Söderberg BC. G. Tetrahedron 2007; 63: 7077