Rearrangement of β,γ-unsaturated esters with thallium trinitrate: synthesis of indans bearing a α-keto ester moiety

Journal of the Brazilian Chemical Society

Volumn 17, Issue 1, 2006, Pages 200-205

  Silva Jr , Luiz F ^a   Pedrozo, Eliane C ^a   Ferraz, Helena M C ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Indan; Ring contraction; Thallium trinitrate; keto ester

Indexed keywords

EID: 32444433261     PISSN: 01035053     EISSN: 01035053     Source Type: Journal    
DOI: 10.1590/s0103-50532006000100029     Document Type: Article

References (21)

1. For an account concerning the synthesis of indans, see: Ferraz, H.M.C.; Aguilar, A.M.; Silva, L.F., Jr.; Craveiro, M.V.; Quim. Nova 2005, 28, 703. Available free of charge at http://quimicanova.sbq.org.br/quimicanova.htm.
2. For a leading reference concerning Indinavir® (Name: D-erythro-Pentonamide, 2,3,5-trideoxy-N-[(1S,2R)-2,3-dihydro-2-hydroxy-1H-inden- 1-yl]-5-[(2 S)-2-[[(1,1-dimethylethyl)amino]carbonyl]-4-(3-pyridinylmethyl)-1- piperazinyl]-2-(phenylmethyl)- (9CI); CAS number: 150378-17-9), see: Dorsey, B.D.; Levin, R.B.; McDaniel, S.L.; Vacca, J.P.; Guare, J.P.; Darke, P.L.; Zugay, J.A.; Emini, E.A.; Schleif, W.A.; Quintero, J.C.; Lin, J.H.; Chen, I.-W.; Holloway, M.K.; Fitzgerald, P.M.D.; Axel, M.G.; Ostovic, D.; Andersen, P.S.; Huff, J.R.; J. Med. Chem. 1994, 37, 3443.
3. For a leading reference concerning Aricept® (Name: 1H-Inden-1 -one, 2,3-dihydro-5,6-dimethoxy-2- [[1 -(phenylmethyl)-4-piperidinyl]methyl]-, hydrochloride (9CI); CAS number: 120011-70-3), see: Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K.; J. Med. Chem. 1995, 38, 4821.
4. Ferraz, H.M.C.; Silva, L.F., Jr.; Tetrahedron 2001, 57, 9939.
5. Ferraz, H.M.C.; Silva, L.F., Jr.; Vieira, T.O.; Tetrahedron 2001, 57, 1709.
6. Ferraz, H.M.C.; Silva, L.F., Jr.; Synthesis 2002, 1033.
7. Ferraz, H.M.C.; Aguilar, A.M.; Silva, L.F., Jr.; Synthesis 2003, 7, 1031.
8. Ferraz, H.M.C.; Aguilar, A.M.; Silva, L.F., Jr.; Tetrahedron 2003, 59, 5817.
9. Silva, L.F., Jr.; Sousa, R.M.F.; Ferraz, H.M.C.; Aguilar, A.M.; J. Braz. Chem. Soc. 2005, 16, 1160. Available free of charge at http://jbcs.sbq.org.br.
10. Ferraz, H.M.C.; Grazini, M.V.A.; Silva, L.F., Jr.; Longo, L.S., Jr.; Synth. Commun. 1999, 29, 1953.
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12. Majima, K.; Tosaki, S. Y.; Ohshima, T.; Shibasaki, M.; Tetrahedron Lett. 2005, 46, 5377;
13. Zhang, J.; Blazecka, P.G.; Angell, P.; Lovdahl, M.; Curran, T.T.; Tetrahedron 2005, 61, 7807.
14. Taylor, B.C.; Robey, R.L.; Liu, K.-T.; Favre, B.; Bozimo, H.T.; Conley, R.A.; Chiang, C.-S.; McKillop, A.; Ford, M.E.; J. Am. Chem. Soc. 1976, 98, 3037.
15. For a similar strategy, see ref. 6.
16. The relative configuration was established by comparison to the NMR data of similar indans. See, for example, ref. 4 and 8.
17. The effect of electron-donating and electron-withdrawing groups in the thallium(III)-promoted ring contraction reaction has been previously discussed in ref. 7 and 9.
18. The coordination of thallium(III) with carboxylic acids and derivatives, including esters, has been previously proposed. See, for example: McKillop, A.; Hunt, J.D.; Zelesko, M.J.; Fowler, J.S.; Taylor, B.C.; McGillivray, G.; Kienzle, F.; J. Am. Chem. Soc. 1971, 93, 4841;
19. Taylor, B.C.; Kienzle, F.; Robey, R.L.; McKillop, A.; Hunt, J.D.; J. Am. Chem. Soc. 1971, 93, 4845;
20. Larock, R.C.; Fellows, C.A.; J. Am. Chem. Soc. 1982, 104, 1900;
21. Larock, R.C.; Varaprath, S.; Lau, H.H.; Fellows, C.A.; J. Am. Chem. Soc. 1984, 106, 5274