94250-47-2Relevant academic research and scientific papers
BX 3-Mediated Intermolecular Formation of Functionalized 3-Halo-1 H-indenes via Cascade Halo-Nazarov-Type Cyclization
Fernandes, Rodney A.,Kumari, Anupama
, p. 2245 - 2258 (2020/08/10)
A BX 3-promoted, intermolecular regioselective synthesis of 3-halo-functionalized 1 H-indenes from 4-oxo-4 H-chromene-3-carb?-aldehydes and alkynes has been developed. BX 3 displays a dual role of Lewis acid catalyst and halide source for haloallyl cation formation for the intended halo-Nazarov-type cyclization. The overall transformation represents an efficient cascade annulation that employs readily available starting materials, inexpensive reagents and a convenient and mild reaction procedure to generate halo-functionalized indenes (45 examples). The reaction was also extended to 8-formylcoumarins to deliver coumarin-based 3-halo-1 H-indenes in 79-95percent yield (6 examples). The reaction involves conversion of the aldehyde into an sp 3 carbon with two new C-C bonds and additionally a C-X bond is formed (X = halide).
An efficient method for the synthesis of β-dicarbonyl enones using polymer-supported N, N-diethylbenzeneselenenamide
Sheng, Shou-Ri,Wei-Zhou,Liu, Xiao-Ling
, p. 552 - 553 (2007/10/03)
A novel polystyrene-supported N, N-diethylbenzeneselenenamide reagent has been prepared. Reaction of the resin with β-formylcycloanones and subsequent oxidative deselenation afforded β-dicarbonyl enones in good yields and high purities.
Annulation of α-Formyl α,β-Unsaturated Ketones by a Michael Addition-Cyclization Sequence. A Versatile Synthesis of Alicyclic Six-Membered Rings.
Meyer, Walter L.,Brannon, Michael J.,Burgos, Celmira da G.,Goodwin, Thomas E.,Howard, Ralph W.
, p. 438 - 447 (2007/10/02)
The potential generality of the annulation sequence shown in Scheme II (10 -> 11 -> 12 -> 13 -> 14/15) has been examined in model systems.Dehydrogenation of α-formylcyclohexanones 11a-d with 1 equiv of DDQ rapidly produces α,β-unsaturated α-formyl ketones
A Simple Method for the Efficient Synthesis of Unsaturated β-Dicarbonyl Compounds
Liotta, Dennis,Barnum, Christopher,Puleo, Robert,Zima, George,Bayer, Charlene,Kezar, Hollis S.
, p. 2920 - 2923 (2007/10/02)
β-Dicarbonyl compounds which are substantially enolized can be readily converted to their corresponding unsaturated derivative by (a) selenation using a 1:1 complex of phenylselenenyl chloride/pyridine and (b) in situ oxidation with 30percent H2O2 (after removal of the pyridine).The isolated yields of unsaturated β-dicarbonyl compounds obtained in this way are typically between 80percent and 100percent.If the selenation step (step a) is carried out in the presence of excess reagent, a slow ''nonoxidative'' elimination occurs.Synthetic and mechanistic details of this ''nonoxidative''process are discussed.
