Synthesis of N-protected/free indole-7-carboxaldehyde

Synthetic Communications

Volumn 37, Issue 24, 2007, Pages 4343-4352

  Mohanakrishnan, Arasambattu K ^a   Balamurugan, Ramalingam ^a   Ramesh, Neelamegam ^a   Mathiselvam, Manoharan ^a   Manavalan, Subramaniam ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

7 cyanomethylindole; 7 hydroxyindole; Bromomethylindole; Indole 7 carboxaldehyde

Indexed keywords

ALDEHYDE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 37249082166     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701578586     Document Type: Article

References (25)

1. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
2. (a) Eenkhoom, J. A.; Desilva, O. S.; Snieckus, V. J. Synthesis of 1-(2-indolyl)-2-arylethylene derivatives. J. Chem. Soc., Chem. Commun. 1970, 1095-1096;
3. (b) Sundberg, R. J.; Russel, H. F. Syntheses with N-protected 2-lithioindoles. J. Org. Chem. 1973, 38, 3324-3330;
4. (c) Katritzky, A. R.; Akutagawa, K. Carbon dioxide: a reagent for the protection of nucleophilic centres and the simultaneous activation of alternative locations to electrophilic attack, part I: a new synthetic method for the 2-substitution of 1-unsubstituted indoles. Tetrahedron Lett. 1985, 26, 5935-5938;
5. (d) Katritzky, A. R.; Akutagawa, K. Carbon dioxide: a reagent for simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack, V: activation of the 2-alkyl group of a 2-alkylindole toward proton loss and subsequent electrophilic substitution. J. Am. Chem. Soc. 1986, 108, 6808-6809;
6. (e) Inagaki, S.; Naruse, Y.; Ito, Y. Highly regioselective functionalization of 2,3-dialkyl substituents on indoles. J. Org. Chem. 1991, 56, 2256-2258.
7. Gribble, G. W. Recent developments in indole ring synthesis - Methodology and applications. J. Chem. Soc., Perkin Trans. 1 2000, 1045-1107.
8. Moyer, M. P.; Shiurba, J. F.; Rapoport, H. Metal-halogen exchange of bromoindoles: a route to substituted indoles. J. Org. Chem. 1986, 51, 5106-5110.
9. Bartoli, G.; Palmier, G.; Bosco, M.; Dalpozzo, R. The reaction of vinyl Grignard reagents with 2-substituted nitroarenes: a new approach to the synthesis of 7-substituted indoles. Tetrahedron Lett. 1989, 30, 2129-2132.
10. Dobson, D. R.; Gilmore, J.; Long, D. A. Synthesis of 7-formylindole using the Bartoli indole methodology. Synlett 1992, 79-80.
11. Dobbs, A. P.; Voyle, M.; Whittall, N. Synthesis of novel indole derivatives: variations in the Bartoli reaction. Synlett 1999, 1594-1596.
12. Pirrung, M. C.; Wedel, M.; Zhao, Y. 7-Alkyl indole synthesis via a convenient formation/alkylation of lithionitrobenzenes and an improved Bartoli reaction. Synlett 2002, 143-145.
13. Kolis, S. P.; Clayton, M. T.; Grutsch, J. L.; Faul, M. M. Synthesis of 7-cyano-and 7-acetamido-indoles via cyanocarbonation/hydrogenation of 7-formyl indole. Tetrahedron Lett. 2003, 44, 5707-5710.
14. Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Directed orthometalation approach to C-7-substituted indoles: Suzuki-Miyaura cross-coupling and the synthesis of pyrrolophenanthridone alkaloids. Org. Lett. 2003, 5, 1899-1902.
15. Ishiyama, K.; Yamada, Y. Convenient synthesis of 7-hydroxyindole. Tetrahedron Lett. 2005, 46, 1021-1022.
16. (a) Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H- furo[3,4-b]indole. a new annulation strategy for the construction of ellipticine and isoellipticine. J. Org. Chem. 1984, 49, 4518-4523;
17. (b) Mohanakrishnan, A. K.; Srinivasan, P. C. A versatile construction of the 8H-quino[4,3-b]carbazole ring system as a potential DNA binder. J. Org. Chem. 1995, 60, 1939-1946;
18. (c) Mohanakrishnan, A. K.; Srinivasan, P. C. Synthesis of 3-aryl-5H-pyrido[4,3-b]indoles. Synth. Commun. 1995, 25, 2415-2424;
19. (d) Mohanakrishnan, A. K.; Srinivasan, P. C. Synthesis of 4-substituted-1,2,3,4-tetrahydro-β-carbolines via intramolecular radical cyclisation and Heck reaction. Tetrahedron Lett. 1996, 37, 2659-2662.
20. Batcho, A. D.; Leimgruber, W. Indoles from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction: 4-benzyloxyindole. Org. Synth. Coll. Vol. VII, 1990, 34.
21. Mohanakrishnan, A. K.; Balamurugan, R.; Ramesh, N. A facile preparation of N-protected indolaldehydes using a modified Hass procedure. Tetrahedron Lett. 2005, 46, 8189-8193.
22. Mehta, G.; Panda, G. A new synthesis of corannulene. Tetrahedron Lett. 1997, 38, 2145-2148.
23. Pindur, U.; Kim, Y.- S.; Mehrabani, F. Advances in indolo[2,3-a]carbazole chemistry: design and synthesis of protein kinase C and topoisomerase I inhibitors. Curr. Med. Chem. 1999, 6, 29-70.
24. (a) Mantos, E. K.; Clardy, J. The synthesis of dithyreanitrile. Tetrahedron Lett. 1993, 34, 1085-1086;
25. (b) Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. Dictyodendrins A-E, the first telomerase-inhibitory marine natural products from the sponge Dictyodendrilla verongiformis. J. Org. Chem. 2003, 68, 2765-2770.