Synthesis and transformations of ethyl 3-(benzoylamino)-1H-indole-2- carboxylates

Synthesis

Volumn , Issue 11, 2008, Pages 1741-1746

  Čuček, Karmen ^a   Verček, Bojan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Cyclization; Fischer indole synthesis; Hydrazones; Indoles; Rearrangement

Indexed keywords

ADDITION REACTIONS; ALKALI METALS; AMIDES; ESTERS; HEATING; MATHEMATICAL TRANSFORMATIONS; MICROFLUIDICS; ORGANIC COMPOUNDS; SODIUM;

AQUEOUS SODIUM HYDROXIDE; BENZAMIDE; DECARBOXYLATION REACTIONS; HYDRAZINE HYDRATE (HZH); POLYPHOSPHORIC ACID (PPA); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

CARBOXYLATION;

3 (BENZOYLAMINO) 5 CHLORO 1H INDOLE 2 CARBOXYLIC ACID; BENZAMIDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER; ETHYL 3 (BENZOYLAMINO) 5 CHLORO 1H INDOLE 2 CARBOXYLATE; HYDRAZIDE; HYDRAZINE; INDOLE DERIVATIVE; N (5 CHLORO 1H INDOL 3 YL)BENZAMIDE; PHENYLHYDRAZONE DERIVATIVE; POLYPHOSPHATE; SODIUM HYDROXIDE;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DECARBOXYLATION; HEATING; HYDROLYSIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 45249108662     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067025     Document Type: Article

References (27)

1. (a) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry, Vol. 4;
2. Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, 313.
3. (b) Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 119.
4. (c) Gribble, G. W. In Comprehensive Heterocyclic Chemistry II, Vol. 2;
5. Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996, 207.
6. See, for example: Kranjc, K; Kočevar, M. Tetrahedron 2008, 64, 45; and references cited therein.
7. Salituro, F. G.; Tomlinson, R. C.; Baron, B. M; Demeter, D. A.; Weintraub, H. J. R.; McDonald, I. A. Bioorg. Med. Chem.Lett. 1991, 1,455.
8. Monge, A.; Palop, J. A.; Recalde, I.; Martinez-Crespo, F.; Fernández-Alvarez, E. An. Quim., Ser. C 1985, 81, 267.
9. Kurilo, G. N.; Boyarintseva, O. N.; Grinev, A. N. Khim. Geterotsikl. Soedin. 1975, 664;
10. Chem. Abstr. 1975, 83, 114137u.
11. Lenaršič, R.; Kočevar, M.; Polanc, S. J. Org. Chem. 1999, 64, 2558.
12. (a) Unangst, P. C. J. Heterocycl. Chem. 1983, 20, 495.
13. (b) Viti, G.; Giannotti, D.; Nannicini, R.; Ricci, R.; Pestellini, V. J. Heterocycl. Chem. 1991, 28, 379.
14. See, for example: Liu, K. G.; Robichaud, A. J.; Lo, J. R.; Mattes, J. F.; Cai, Y. Org. Lett. 2006, 8, 5769.
15. Joule, J. A. In Science of Synthesis, Vol. 10;
16. Thomas, E. J., Ed.; Georg Thieme Verlag: Stuttgart, 2006, 361.
17. (a) Čuček, K; Verček, B. Synlett 1999, 120.
18. (b) Čuček, K.; Golobič, A.; Verček, B. Heterocycles 2007, 73, 555.
19. Sundberg, R. J. Indoles, In Best Synthetic Methods; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1996, 1.
20. See, for example: Acheson, R. M.; Booth, S. R. G. J. Chem. Soc. C 1968, 30; and references cited therein.
21. (a) Morales-Ríos, M. S.; Espiñeira, J.; Joseph-Nathan, P. Magn. Reson. Chem. 1987, 25, 377.
22. (b) Lee, M.; Phillips, R. S. Magn. Reson. Chem. 1992, 30, 1035.
23. (c) Burton, G.; Ghini, A. A.; Gros, E. G. Magn. Reson. Chem. 1986, 24, 829.
24. (d) Morales-Ríos, M. S.; del Río, R. E.; Joseph-Nathan, P. Magn. Reson. Chem. 1988, 26, 552.
25. (e) Joseph-Nathan, P.; del Río, R. E.; Morales-Ríos, M. S. Heterocycles 1988, 27, 377.
26. Monge, A.; Palop, J. A.; Parrado, P.; Perez-Ilzarbe, C. J. Heterocycl. Chem. 1987, 24, 437.
27. Salituro, F. G.; Baron, B. M. EP483,881 1992, Chem. Abstr. 1992, 117, 90153p.