Abstract:
On heating in glacial acetic acid (or ethanol in the presence of manganese(ii) acetate), 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one undergoes unusual transformation into 2,6-diphenyl-4-trifluoromethylpyridine. The regioisomeric β-aminovinyl ketone, viz. 1-amino-4,4,4-trifluoro-1-phenylbut-1-en-3-one, remains unchanged under similar reaction conditions.
Citation:
V. I. Filyakova, N. S. Boltacheva, P. A. Slepukhin, M. G. Pervova, V. N. Charushin, “Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine”, Mendeleev Commun., 30:5 (2020), 676–678
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https://www.mathnet.ru/eng/mendc1291
https://www.mathnet.ru/eng/mendc/v30/i5/p676
This publication is cited in the following 4 articles:
Ruslan S. Shulgin, Ol'ga G. Volostnykh, Anton V. Stepanov, Igor' A. Ushakov, Olesya A. Shemyakina, “Organic Base-Catalyzed Cascade Reaction of CF3–Iminopropargylic Alcohols with Carboxylic Acids: an Approach to β-CF3 β-Aminoenones”, J. Org. Chem., 2025
V. I. Filyakova, N. S. Boltacheva, M. G. Pervova, V. N. Charushin, “Synthesis of 4′-trifluoromethyl- and 4′-difluoromethyl-2,2′:6′,2″-terpyridines”, Russ Chem Bull, 73:6 (2024), 1709
Yu. O. Edilova, Yu. S. Kudyakova, P. A. Slepukhin, V. I. Saloutin, D. N. Bazhin, “Heteroannelated Enaminoketones Derived from 1,2,4-Triketone Analogs”, Russ J Gen Chem, 93:S1 (2023), S10
Vera I. Filyakova, Nadezhda S. Boltacheva, Marina G. Pervova, Valery N. Charushin, “A new synthesis of 4′-trifluoromethyl-2,2′:6′,2″-terpyridine”, Mendeleev Communications, 31:3 (2021), 388
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