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For a related recent example, see
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For a related recent example, see: Kearney, A. M.; Vanderwal, C. D. Angew. Chem., Int. Ed. 2006, 45, 7803-7806.
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38849134502
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The use of a tertiary amine in these reactions is recommended (see refs 6 and 7). Its role can be to facilitate elimination of diethylamine from the primary adduct of the reaction, but this was not proven yet.
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The use of a tertiary amine in these reactions is recommended (see refs 6 and 7). Its role can be to facilitate elimination of diethylamine from the primary adduct of the reaction, but this was not proven yet.
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(a) Nguyen, T. M.; Sanchez-Salvatori, M. d. R.; Wypych, J.-C.; Marazano, C. J. Org. Chem. 2007, 72, 5916-5919.
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For a review on the synthesis and reactions of glutaconaldehyde and the corresponding amino derivatives aminopentadienals, see: Becher, J. Synthesis 1980, 589-612
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(b) For a review on the synthesis and reactions of glutaconaldehyde and the corresponding amino derivatives (aminopentadienals), see: Becher, J. Synthesis 1980, 589-612.
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A similar reaction was reported starting from a diaryl ketone and using a chlorovinamidinium salt. The chloropyridine obtained in 35% yield was further reduced to give a 2,3-diarylpyridine: Simoni, D.; Grisolia, G.; Giannini, G.; Roberti, M.; Rondanin, R.; Piccagli, L.; Barrichello, R.; Rossi, M.; Romagnoli, R.; Invidiata, F. P.; Grimaudo, S.; Jung, M. K.; Hamel, E.; Gebbia, N.; Crosta, L.; Abbadessa, V.; Di Cristina, A.; Dusonchet, L.; Meli, M.; Tolomeo, M. J. Med. Chem. 2005, 48, 723-736.
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A similar reaction was reported starting from a diaryl ketone and using a chlorovinamidinium salt. The chloropyridine obtained in 35% yield was further reduced to give a 2,3-diarylpyridine: Simoni, D.; Grisolia, G.; Giannini, G.; Roberti, M.; Rondanin, R.; Piccagli, L.; Barrichello, R.; Rossi, M.; Romagnoli, R.; Invidiata, F. P.; Grimaudo, S.; Jung, M. K.; Hamel, E.; Gebbia, N.; Crosta, L.; Abbadessa, V.; Di Cristina, A.; Dusonchet, L.; Meli, M.; Tolomeo, M. J. Med. Chem. 2005, 48, 723-736.
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Free glutacondialdehyde derivatives are very unstable intermediates (glutaconaldehyde is stable for only ∼30 mn at ∼-70°C (see ref 10b) or prone to dimerization see ref 5
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Free glutacondialdehyde derivatives are very unstable intermediates (glutaconaldehyde is stable for only ∼30 mn at ∼-70°C (see ref 10b) or prone to dimerization (see ref 5)).
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84918028952
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Becher, J.; Haunso, N.; Pedersen, T. Acta. Chim. Scand. B 1975, 29, 124-132.
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