Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes

Journal of Organic Chemistry

Volumn 69, Issue 16, 2004, Pages 5476-5479

  Kashulin, Igor A ^a   Nifant'ev, Ilya E ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANE; LITHIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DILITHIUM COMPOUNDS; METALATION;

KETONES;

BUTYLLITHIUM; CARBAMIC ACID DERIVATIVE; DIAMINE DERIVATIVE; ETHYL N,N DIMETHYLCARBAMATE; HETARENOINDANONE; INDANONE DERIVATIVE; LITHIUM DERIVATIVE; N,N,N',N' TETRAMETHYLENEDIAMINE; POTASSIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; WOLFF KISHNER REDUCTION;

EID: 3543021476     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049504w     Document Type: Article

References (29)

1. Laishevtsev, I. P.; Kashulin, I. A.; Taidakov, I. V.; Bagrov, V. V.; Nifant'ev I. E. Chem. Heterocycl. Compd. 2003, 39, 553.
2. For heterocyclic analogues of fluorene, see: (a) Nifant'ev, I. E.; Bagrov, V. V. PCT WO 99/24446.
3. (b) Resconi, L.; Guidotti, S.; Baruzzi, G.; Grandini, C.; Kashulin, I. A.; Ivchenko, P. V.; Nifant'ev, I. E. PCT WO 01/53360.
4. (c) Johnson, K. W.; Merrick-Mack, J. A.; Mack, M. P.; Nagy, S.; Wang, S.; Lee, C. C.; Lynch, M. W.; Mutchler, J. A.; Tsuie, B. M.; Neal-Hawkins, K. L. PCT WO 03/089485.
5. (d) Grandini, C.; Camurati, I.; Guidotti, S.; Mascellani, N.; Resconi, L.; Nifant'ev, I. E.; Kashulin, I. A.; Ivchenko, P. V.; Mercandelli, P.; Sironi, A. Organometallics 2004, 23, No. 3, 344.
6. (e) Mack, M. P.; Nagy, S.; Wang, S.; Lee, C. C.; Tsuie, B. M.; Hlatky, G. G.; Meverden, C. C. PCT WO 2004/013194.
7. For heterocyclic analogues of indene, see: (a) Jones, R. L. J.; Dubitsky, Y. A.; Elder, M. J.; Ewen, J. A. PCT WO 98/22486.
8. (b) Ewen, J. A.; Jones, R. L.; Elder, M. J.; Rheingold, A. L.; Liable-Sands, L. M. J. Am. Chem. Soc. 1998, 120, 10786.
9. (c) Resconi, L.; Guidotti, S.; Laishevtsev, I. P.; Nifant'ev, I. E. EP 1157027, 2001.
10. (d) Dall'oco, T.; Fusco, O.; Galimberti, M.; Nifant'ev, I. E.; Laishevtsev, I. P. EP 1157046, 2001.
11. (e) Ewen, J. A.; Elder, M. J.; Jones, R. L.; Rheingold, A. L.; Liable-Sands, L. M.; Sommer, R. D. J. Am. Chem. Soc. 2001, 123, 4763.
12. (f) Dall'oco, T.; Fusco, O.; Laishevtsev, I. P.; Nifant'ev, I. E. EP1226193, 2002.
13. (g) Ryabov, A. N.; Izmer, V. V.; Borisenko, A. A.; Canich, J. A. M.; Kuz'mina, L. G.; Howard, J. A. K.; Voskoboynikov, A. Z. J. Chem. Soc., Dalton Trans. 2002, 15, 2995.
14. (h) Temme, R. B.; Fisher, R. A. U.S. Patent 6451938, 2002.
15. (i) Ryabov, A. N.; Gribkov, D. V.; Izmer, V. V.; Voskoboynikov A. Z. Organometallics 2002, 21, 2842
16. MacDowell, D. W. H.; Patrick, T. B. J. Org. Chem. 1967, 32, 2441.
17. Guillaumel, J.; Boccara, N.; Demerseman, P. J. Heterocycl. Chem. 1990, 27, 1047.
18. Sauter, F.; Dzerovicz, A. Monatsh. Chem. 1969, 100, 913.
19. Sauter, F.; Deinhammer, W. Monatsh. Chem. 1970, 101, 544.
20. Gattermann, L. Leibigs Ann. Chem. 1912, 393, 113.
21. Campo, M. A.; Larock, R. C. J. Org. Chem. 2002, 67, 5616.
22. Neugebauer, W.; Kos, A. J.; Schleyer, P. R. J. Organomet. Chem. 1982, 228, 107.
23. Michael, U.; Hornfeldt, A.-B. Tetrahedron Lett. 1970, 60, 5219.
24. Talalaeva, T. V.; Kocheshkov, K. A. In Metody Elementorganicheskoi Khimii. Litii, Natrii, Kalii, Rubidii, Tsezii [Methods of Organoelement Chemistry. Lithium, Sodium, Potassium, Rubidium, Cesium]; Nesmeyanov, A. N., Kocheshkov, K. A., Eds.; Nauka, Moscow, 1971; Book 1, p 295.
25. Davies W.; Middleton S. J. Chem. Soc. 1958, 822
26. Faigl, F.; Schlosser, M. Tetrahedron 1993, 49, 10271.
27. Cheeseman, G. W. H.; Greenberg, S. G. J. Organomet. Chem. 1979, 166, 139.
28. Boberg, F.; Czogalla, C.-D.; Torges, K.-F.; Wentrup, G.-J. Liebigs Ann. Chem. 1983, 1598.
29. Brown, F.; Mann, F. G. J. Chem. Soc. 1948, 847.