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4
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33845757016
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Soloshonok V.A. (Ed), ACS Publications Division and Oxford University Press, Washington, DC
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Sani M., Molteni M., Bruché L., Volonterio A., and Zanda M. In: Soloshonok V.A. (Ed). Fluorine-Containing Synthons (2005), ACS Publications Division and Oxford University Press, Washington, DC 572-592
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Sani, M.1
Molteni, M.2
Bruché, L.3
Volonterio, A.4
Zanda, M.5
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6
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10744227548
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Volonterio A., Bellosta S., Bravin F., Bellucci M.C., Bruché L., Colombo G., Malpezzi L., Mazzini S., Meille S.V., Meli M., Ramirez de Arellano C., and Zanda M. Chem. Eur. J. 9 (2003) 4510-4522
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Volonterio, A.1
Bellosta, S.2
Bravin, F.3
Bellucci, M.C.4
Bruché, L.5
Colombo, G.6
Malpezzi, L.7
Mazzini, S.8
Meille, S.V.9
Meli, M.10
Ramirez de Arellano, C.11
Zanda, M.12
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8
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25144461176
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Black W.C., Bayly C.I., Davis D.E., Desmarais S., Falgueyret J.-P., Léger S., Li C.S., Massé F., McKay D.J., Palmer J.T., Percival M.D., Robichaud J., Tsou N., and Zamboni R. Bioorg. Med. Chem. Lett. 15 (2005) 4741-4744
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Black, W.C.1
Bayly, C.I.2
Davis, D.E.3
Desmarais, S.4
Falgueyret, J.-P.5
Léger, S.6
Li, C.S.7
Massé, F.8
McKay, D.J.9
Palmer, J.T.10
Percival, M.D.11
Robichaud, J.12
Tsou, N.13
Zamboni, R.14
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9
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33144484033
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Li C.S., Deschenes D., Desmarais S., Falgueyret J.-P., Gauthier J.Y., Kimmel D.B., Léger S., Massé F., McGrath M.E., McKay D.J., Percival M.D., Riendeau D., Rodan S.B., Thérien M., Truong V.-L., Wesolowski G., Zamboni R., and Black W.C. Bioorg. Med. Chem. Lett. 16 (2006) 1985-1989
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Li, C.S.1
Deschenes, D.2
Desmarais, S.3
Falgueyret, J.-P.4
Gauthier, J.Y.5
Kimmel, D.B.6
Léger, S.7
Massé, F.8
McGrath, M.E.9
McKay, D.J.10
Percival, M.D.11
Riendeau, D.12
Rodan, S.B.13
Thérien, M.14
Truong, V.-L.15
Wesolowski, G.16
Zamboni, R.17
Black, W.C.18
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13
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0000272211
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Roques B.P., Lucas-Soroca E., Chaillet P., Costentin J., and Fournié-Zaluski M.C. Proc. Natl. Acad. Sci. U.S.A. 80 (1983) 3178-3182
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, vol.80
, pp. 3178-3182
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Roques, B.P.1
Lucas-Soroca, E.2
Chaillet, P.3
Costentin, J.4
Fournié-Zaluski, M.C.5
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14
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33845795463
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note
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3): δ 7.29 (m, 5H), 4.39 (m, 1H), 4.21 (m, 2H), 4.03 (d, J = 13.2 Hz, 1H), 3.85 (d, J = 13.2 Hz, 1H), 3.79 (m, 1H), 3.43 (dd, J = 16.2 and 9.4 Hz, 1H), 3.11 (dd, J = 16.2 and 4.1 Hz, 1H), 2.39 (m, 1H), 0.92 (d, J = 7.1 Hz, 3H), 0.84 (d, J = 6.8 Hz, 3H).
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15
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0033550292
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note
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Another possible pathway to 6 could be the fragmentation into ketene 7 and the corresponding deacylated 2-oxazolidinone, followed by reaction with benzylamine.{A figure is presented} The protic acids successfully used in Table 1, entries 1-5,11 could therefore play the role of rapidly quenching the intermediate α-carbonyl carbanion formed by aza-Michael addition, thus suppressing the fragmentation via ketene 7. The formation of ketenes by fragmentation of N-acyl-oxazolidinones has been observed previously: Bravo, P.; Fustero, S.; Guidetti, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1999, 64, 8731-8735 and references cited therein. Attempts to isolate these hypothetic ketene intermediates by adding external nucleophiles, such as dialkylamines, in the reaction mixture were unsuccessful.
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17
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33845725891
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note
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3): δ 7.33-7.18 (m, 5H), 4.41 (m, 1H), 4.23 (m, 2H), 3.86 (m, 1H), 3.49-3.32 (m, 4H), 3.04 (dd, J = 16.6 and 3.9 Hz, 1H), 2.85 (dd, J = 13.5 and 7.3 Hz, 1H), 2.74 (dd, J = 13.5 and 6.2 Hz, 1H), 2.40 (m, 1H), 1.61 (br s, 1H), 0.91 (d, J = 6.9 Hz, 3H), 0.86 (d, J = 6.9 Hz, 3H).
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-
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18
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33845740525
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note
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D -23.3 (c 0.6, methanol).
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19
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33845790392
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note
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Compounds 1 are indefinitely stable upon storage at 4 °C (neat). However, the stability is much lower when diastereomers 1 are stored in solution at room temperature, and definitely low when heated in the presence of bases, and in general at pH > 7. This precluded, in our hands, the possibility to isolate diastereopure 1 by crystallization with chiral bases.
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21
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0027475050
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Roques B.P., Noble F., Daugé V., Founie-Zaluski M.C., and Beaumont A. Pharmacol. Rev. 45 (1993) 87-146
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(1993)
Pharmacol. Rev.
, vol.45
, pp. 87-146
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Roques, B.P.1
Noble, F.2
Daugé, V.3
Founie-Zaluski, M.C.4
Beaumont, A.5
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22
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0028243867
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Gomez-Monterrey I., Beaumont A., Nemecek P., Roques B.P., and Fournie-Zaluski M.-C. J. Med. Chem. 37 (1994) 1865-1873
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(1994)
J. Med. Chem.
, vol.37
, pp. 1865-1873
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Gomez-Monterrey, I.1
Beaumont, A.2
Nemecek, P.3
Roques, B.P.4
Fournie-Zaluski, M.-C.5
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23
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0029970468
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and references cited therein
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Coric P., Turcaud S., Meudal H., Roques B.P., and Fournie-Zaluski M.C. J. Med. Chem. 39 (1996) 1210-1219 and references cited therein
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(1996)
J. Med. Chem.
, vol.39
, pp. 1210-1219
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Coric, P.1
Turcaud, S.2
Meudal, H.3
Roques, B.P.4
Fournie-Zaluski, M.C.5
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