Indium(III) chloride/2-iodoxybenzoic acid: A novel reagent system for the conversion of indoles into isatins

Synthesis

Volumn , Issue 5, 2007, Pages 693-696

  Yadav, J S ^a   Subba Reddy, B V ^a   Reddy, Ch Suresh ^a   Krishna, A D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Hypervalent iodine; Indium(III) reagents; Indole; Isatin

Indexed keywords

HYPERVALENT IODINE; INDIUM(III) REAGENTS; INDOLE;

BENZENE; INDIUM COMPOUNDS; IODINE; ORGANIC ACIDS;

NITROGEN COMPOUNDS;

1 BENZYL 1H INDOLE 2,3 DIONE; 1 BENZYL 5 NITRO 1H INDOLE 2,3 DIONE; 1 METHYL 1H INDOLE 2,3 DIONE; 2 IODYLBENZOIC ACID; 5 BROMO 1 METHYL 1H INDOLE 2,3 DIONE; BENZOIC ACID DERIVATIVE; INDIUM CHLORIDE IN 111; INDOLE DERIVATIVE; ISATIN DERIVATIVE; METHYL 2,3 DIONE DIHYDRO 1H INDOLE 5 CARBOXYLATE; REAGENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; DRUG SYNTHESIS; OXIDATION;

EID: 33947596309     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965930     Document Type: Article

References (22)

1. da Silva, J. F. M.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273.
2. Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197.
3. Nakamura, T.; Shirokawa, S.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S. Org. Lett. 2006, 8, 677.
4. (a) Parrick, J.; Yahya, A.; Ijaz, A. S.; Yizun, J. J. Chem. Soc., Perkin Trans. 1 1989, 2009.
5. (b) Tatsugi, J.; Zhiwei, T.; Izawa, Y. ARKIVOC 2001, (i), 67; www.arkat-usa.org.
6. (c) Gassman, P. G.; Cue, B. W. Jr.; Luh, T.-Y. J. Org. Chem. 1977, 42, 1344.
7. Noland, W. E.; Rieke, R. D. J. Org. Chem. 1962, 27, 2250.
8. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: San Diego, 1997.
9. (b) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271.
10. (a) Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
11. (b) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
12. (c) Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int. 1997, 29, 409.
13. Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812.
14. (a) Nicolaou, K. C.; Montagnon, T.; Baran, P. S. Angew. Chem. Int. Ed. 2002, 41, 993.
15. (b) Nicolaou, K. C.; Barn, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233.
16. (a) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
17. (b) Babu, G.; Perumal, P. T. Aldrichimica Acta 2000, 33, 16.
18. (c) Ghosh, R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40, 550.
19. (a) Yadav, J. S.; Sunny, A.; Reddy, B. V. S.; Sabitha, G. Tetrahedron Lett. 2001, 42, 8063.
20. (b) Yadav, J. S.; Reddy, B. V. S.; Kumar, G. M. Synlett 2001, 1781.
21. (c) Yadav, J. S.; Reddy, B. V. S.; Sabitha, G.; Prabhakar, A.; Kunwar, A. C. Tetrahedron Lett. 2003, 44, 2221.
22. (d) Yadav, J. S.; Reddy, B. V. S.; Reddy, Ch. S. Tetrahedron Lett. 2004, 45, 4583.