Synthesis of 3-(arylthio)indoles and related compounds by reactions of metalated aromatics or heterocycles with protected 3,3′-dithiobisindoles

Synthesis

Volumn , Issue 17, 2007, Pages 2690-2698

  Shirani, Hamid ^a   Janosik, Tomasz ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Grignard reagents; Indoles; Lithiation; Sulfides; Thioindoles

Indexed keywords

GRIGNARD REAGENTS; HETEROCYCLES; INDOLES; LITHIATION; THIOINDOLES;

NITROGEN COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

1 (4 METHYLPHENYLSULFONYL) 3 (4 METHOXYPHENYL)THIO 1H INDOLE; 1 (4 METHYLPHENYLSULFONYL) 3 (BENZO[B]THIOPHEN 2 YL)THIO 1H INDOLE; 1 (TERT BUTOXYCARBONYL) 2 METHYL 3 (1 NAPHTHYL)THIO 1H INDOLE; 1 (TERT BUTOXYCARBONYL) 2 METHYL 3 (BENZO[B]FURAN 2 YL)THIO 1H INDOLE; 1 (TERT BUTOXYCARBONYL) 3 PHENYLTHIO 1H INDOLE; 1 PHENYLSUFONYL 3 (BENZO[B]THIOPHEN 2 YL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (1 NAPHTHYL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (2 ETHOXYCARBONYLPHENYL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (3 METHYLPHENYL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (4 ETHOXYCARBONYLPHENYL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (4 METHOXYPHENYL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (9 PHENANTHREN 2 YL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (BIPHENYL 2 YL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 (THIOPHEN 2 YL)THIO 1H INDOLE; 1 PHENYLSULFONYL 3 PHENYLTHIO 1H INDOLE; 2 (1 PHENYLSULFONYL 1H INDOL 3 YL)THIO 1H INDOLE; 3 THIOINDOLE DERIVATIVE; 3,3' DITHIOBIS(1 PHENYLSULFONYL 1H INDOLE); 3,3' DITHIOBIS(1H INDOLE); 3,3' DITHIOBIS(2 METHYL 1H INDOLE); 3,3' DITHIOBIS(5 METHOXY 1 PHENYLSULFONYL 1H INDOLE); 3,3' DITHIOBIS(5 METHOXY 1H INDOLE); 3,3' DITHIOBIS[1 (4 METHYLPHENYLSULFONYL) 1H INDOLE]; 3,3' DITHIOBIS[1 (TERT BUTOXYCARBONYL) 1H INDOLE]; 3,3' DITHIOBIS[1 (TERT BUTOXYCARBONYL) 2 METHYL 1H INDOLE]; 3,3' DITHIOBISINDOLE DERIVATIVE; 5 METHOXY 1 PHENYLSULFONYL 3 (2 ETHOXYCARBONYLPHENYL)THIO 1H INDOLE; 5 METHOXY 1 PHENYLSULFONYL 3 (THIOPHEN 2 YL)THIO 1H INDOLE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; LITHIATION;

EID: 34548691450     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983818     Document Type: Article

References (26)

1. (a) De Martino, G.; La Regina, G.; Coluccia, A.; Edler, M. C.; Barbera, M. C.; Brancale, A.; Wilcox, E.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2004, 47, 6120.
2. (b) De Martino, G.; Edler, M. C.; La Regina, G.; Coluccia, A.; Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale, A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947.
3. Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani, S. K.; Condra, J. H.; Emini, E. A.; Goldman, M. E.; Greenlee, W. J.; Kauffman, L. R.; O'Brien, J. A.; Sardana, V. V.; Schleif, W. A.; Theoharides, A. D.; Anderson, P. S. J. Med. Chem. 1993, 36, 1291.
4. (a) Silvestri, R.; De Martino, G.; La Regina, G.; Artico, M.; Massa, S.; Vargiu, L.; Mura, M.; Loi, A. G.; Marceddu, T.; La Colla, P. J. Med. Chem. 2003, 46, 2482.
5. (b) Silvestri, R.; Artico, M.; De Martino, G.; La Regina, G.; Loddo, R.; La Colla, M.; La Colla, P. J. Med. Chem. 2004, 47, 3892.
6. Ovenden, S. P. B.; Capon, R. J. J. Nat. Prod. 1999, 62, 1246.
7. Atkinson, J. G.; Hamel, P.; Girard, Y. Synthesis 1988, 480.
8. Maeda, Y.; Koyabu, M.; Nishimura, T.; Uemura, S. J. Org. Chem. 2004, 69, 7688.
9. Matsugi, M.; Murata, K.; Gotanda, K.; Nambu, H.; Anilkumar, G.; Matsumoto, K.; Kita, Y. J. Org. Chem. 2001, 66, 2434.
10. Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. Org. Lett. 2004, 6, 819.
11. Tudge, M.; Tamiya, M.; Savarin, C.; Humphrey, G. R. Org. Lett. 2006, 8, 565.
12. Janosik, T.; Shirani, H.; Wahlström, N.; Malky, I.; Stensland, B.; Bergman, J. Tetrahedron 2006, 62, 1699.
13. (a) Yadav, J. S.; Reddy, B. V. S.; Krishna, A. D.; Swamy, T. Tetrahedron Lett. 2003, 44, 6055.
14. (b) Singh, D. U.; Singh, P. R.; Samant, S. D. Tetrahedron Lett. 2004, 45, 9079.
15. Shirani, H.; Stensland, B.; Bergman, J.; Janosik, T. Synlett 2006, 2459.
16. (a) Woodbridge, R. G. III; Dougherty, G. J. Am. Chem. Soc. 1950, 72, 4320.
17. (b) Piotrowska, H.; Serafin, B.; Wejroch-Matacz, K. Rocz. Chem. 1975, 49, 635;
18. Chem. Abstr. 1975, 83, 79019.
19. (a) Illi, V. O. Synthesis 1988, 136.
20. (b) Conway, S. C.; Gribble, G. W. Heterocycles 1990, 30, 627.
21. Grehn, L.; Ragnarsson, U. Angew. Chem., Int. Ed. Engl. 1984, 23, 296.
22. Katritzky, A. R.; Akutagawa, K. Tetrahedron Lett. 1985, 26, 5935.
23. For reviews on generation and applications of functionalized organomagnesium reagents, see: (a) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. V.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem. Int. Ed. 2003, 42, 4302.
24. (b) Ha, H.; Baron, O.; Wagner, A. J.; Knochel, P. Chem. Commun. 2006, 583.
25. Raffa, L. Gazz. Chim. Ital. 1941, 71, 253;
26. Chem. Abstr. 1942, 36, 18620.