Synthesis of dihydrofurans containing trifluoromethyl ketone and heterocycles by radical cyclization of fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes

A Diels–Alder/Ene Cascade Leading to 5‐(Pyrrolidin‐3‐yl)thieno[3,2‐e]isoindoles from Ketone‐derived 2‐Vinylthiophenes and N‐Phenylmaleimide

“…The nuclear Overhauser effect (NOE) analysis of 10d′ showed that it is the E ‐isomer; but a similar NOE analysis was inconclusive for the other mixtures. Because of the availability of 2‐acetylthiophene, the high reactivity of acetone compared with other ketones, and the tendency of 10i to polymerize in the presence of strong acid (based on NMR analysis of the reaction mixtures) compound 10i , was best obtained from 2‐acetylthiophene by the Wittig olefination procedure described by Yilmaz .…”

Synthesis and characterization of piperazine-substituted dihydrofuran derivatives viaMn(OAc)3 mediated radical cyclizations

“…Manganese (III) acetate [29][30][31][32][33] and cerium(IV) ammonium nitrate (CAN) [34][35][36][37][38] are widely used in these reactions. Our research group has reported radical addition and cyclization reactions with CAN [39][40][41][42] and radical cyclization reactions of 1,3-dicarbonyl derivatives with various unsaturated systems, such as conjugated amide derivatives [43][44][45][46][47]and heteroaromatic conjugated alkenes [48][49][50][51].…”

Regio- and diastereoselective synthesis of trans-dihydrofuran-3-carboxamides by radical addition of 1,3-dicarbonyl compounds to acrylamides using manganese(III) acetate and determination of exact configuration by X-ray crystallography

“…Our research group has focused on the radical reaction of 1,3-dicarbonyls and 3-oxopropanenitriles with unsaturated systems. [18][19][20][21][22][23][24][25][26][27] We first reported the reaction of (E)-2-styrylthiophene and (E)-2-methyl-5-styrylfuran with 3-oxopropanenitriles, 18,20 fluorinated-1,3-dicarbonyls 21 and 1,3-diketones 22,23 lead to formation of 2-thienyl and 2-furylsubstituted trans-dihydrofurans (1 and 2). Although there are two possible different cyclization routes with these reactions, we reported that, this cyclization occurs only at the C-1 carbon (adjacent to thienyl or furyl groups) regioselectively ( Figure 1).…”