Efficient synthesis of 5′-fluoroalkoxythiazoles via α-bromo-α-fluoroalkoxyacetophenones Hantzsch type cyclization with thioureas or thioamides
摘要:
Novel alpha-fluoroalkoxyacetophenones were synthesized by addition of the readily available 2,2-dimethoxy-2-phenylethanol to fluoroolefins. alpha-Bromination yielded alpha-bromo-alpha-fluoroalkoxyacetophenones, which on treatment with thioureas or thioamides gave thiazoles with fluoroalkoxy groups at the 5'-position by the Hantzsch-type cyclization. This provides a versatile methodology for the construction of heterocycles from aliphatic fluoroalkoxy containing building blocks. (C) 2012 Elsevier B.V. All rights reserved.
Gubanov, V. A.; Tyul'ga, G. M.; Solodkaya, I. G., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 444 - 448
作者:Gubanov, V. A.、Tyul'ga, G. M.、Solodkaya, I. G.、Sherman, M. A.
DOI:——
日期:——
New Electrophilic Reaction of Perfluoroalkylethylenes. Synthesis and Some Reactions of 1-Halo-1,1,2-trihydroperfluoroalkenes-2
作者:V. A. Petrov
DOI:10.1021/jo00116a031
日期:1995.6
Perfluoroalkylethylenes, R(f)CH=CH2, react with chlorosulfonic acid in the presence of TaF5 or NbF5 catalyst to form allyl chlorides, Z-R(f)CF=CHCH2Cl. These chlorides, or their corresponding bromides, also can be made by the BF3-catalyzed reaction of R(f)CH=CH2 with HCl or HBr in anhydrous HF. The allylic chlorine in the newly synthesized compounds Z-R(f)CF=CHCH2Cl can be easily replaced by reaction with nucleophiles such as I-, Br-, HO-, or (CF3)(2)CFO-.