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Synthesis 2014; 46(15): 2093-2097
DOI: 10.1055/s-0033-1339155
DOI: 10.1055/s-0033-1339155
paper
A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones
Further Information
Publication History
Received: 29 November 2013
Accepted after revision: 10 May 2014
Publication Date:
02 June 2014 (online)
Abstract
A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 °C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084. Included are copies of 1H NMR, 13C NMR and HRMS spectra of compounds 5–11.
- Supporting Information
-
References
- 1 Ahmad K, Thomas NF, Hadi AH. A, Mukhtar MR, Mohamad K, Nafiah MA, Takeya K, Morita H, Litaudon M, Arai H, Awang K. Chem. Pharm. Bull. 2010; 58: 1085
- 2 Menta E, Pescalli N, Spinelli S. Patent PCT Int. Appl. WO 2001009129 A2, 2001 ; Chem. Abstr. 2001, 134, 162922.
- 3 Cincinelli R, Cassinelli G, Dallavalle S, Lanzi C, Merlini L, Botta B, Tuccinardi T, Martinelli A, Penco S, Zunino F. J. Med. Chem. 2008; 51: 7777
- 4 Huber K, Brault L, Fedorov O, Gasser C, Filippakopoulos P, Bullock AN, Fabbro D, Trappe J, Schwaller J, Knapp S, Bracher F. J. Med. Chem. 2012; 55: 403
-
5 Nicolaou KC, Kiappes JL, Tian W, Gondi VB, Becker J. Org. Lett. 2011; 13: 3924
- 6 Hawkins A, Jakubec P, Ironmonger A, Dixon DJ. Tetrahedron Lett. 2013; 54: 365
- 7 Bracher F, Hildebrand D. Tetrahedron 1994; 50: 12329
- 8 Barker MD, Woodward PR, Lewis JR. British Patent Appl. GB 2155462 A, 1985 ; Chem. Abstr. 1986, 104, 207245.
- 9 Csanyi D, Hajos G, Riedl Z, Timari G, Bajor Z, Cochard F, Sapi J, Laronze J.-Y. Bioorg. Med. Chem. Lett. 2000; 10: 1767
- 10 Ritzeler O, Castro A, Grenier L, Soucy F. European Patent Appl. EP 1134221 A1, 2001 ; Chem. Abstr. 2011, 135, 242149.
- 11 Ritzeler O, Castro A, Grenier L, Soucy F, Hancock WW, Mazdiyasni H, Palombella V, Adams J. European Patent Appl. EP 1209158 A1, 2002 ; Chem. Abstr. 2002, 137, 6093.
- 12 Meyers MJ, Trujillo JI, Vernier WF, Anderson DR, Reitz DB, Buchler IP, Hegde SG, Mahoney MW, Wu KK. Patent PCT Int. Appl. WO 2005009370 A2, 2005 ; Chem. Abstr. 2005, 142, 198047.
- 13 Goldberg D, Abeywardane A, Miller C, Morwick T, Netherton M, Snow R, Wang J, Wu J.-P, Xiong Z. US Patent Appl. Publ. US 20060276496 A1, 2006 ; Chem. Abstr. 2006, 146, 45497.
-
14 Thompson MJ, Louth JC, Little SM, Jackson MP, Boursereau Y, Chen B, Coldham I. ChemMedChem 2012; 7: 578
- 15 Bracher F, Hildebrand D. Liebigs Ann. Chem. 1992; 1315
- 16 Abramovitch RA, Shapiro D. J. Chem. Soc. 1956; 4589
- 17 Judd KE, Mahon MF, Caggiano L. Synthesis 2009; 2809
- 18 Atta-ur-Rahman; Ghazala M. Synthesis 1980; 372
- 19 Tahri A, Buysens KJ, Van der Eycken EV, Vandenberghe DM, Hoornaert GJ. Tetrahedron 1998; 54: 13211
-
20 Lin G, Wang Y, Zhou Q, Tang W, Wang J, Lu T. Molecules 2010; 15: 5680
- 21 Cincinelli R, Dallavalle S, Merlini L. Synlett 2008; 1309
- 22 Bobbitt JM, Bourque AJ. Heterocycles 1987; 25: 601
-
23 Johnson JR, Larsen AA, Holley AD, Gerzon K. J. Am. Chem. Soc. 1947; 69: 2364
- 24 Menta E, Nicotra F, Pescalli N, Spinelli S. Patent PCT Int. Appl. WO 0109136 A1, 2001 ; Chem. Abstr. 2001, 134, 163063.
- 25 Lindwall HG, Mantell GJ. J. Org. Chem. 1953; 18: 345
- 26 Herz W, Tsai L. J. Am. Chem. Soc. 1953; 75: 5122