Oxidative Radical Cyclization–Cyclization Reaction Leading to 1H-Benzo[f]isoindole Derivatives
نویسندگان
چکیده
The synthesis of 1H-benzo[f ]isoindole derivatives was achieved by the cascade radical cyclization–cyclization reaction of the active methine substrate having an allyl group and phenyl group as different two radical acceptors. This oxidative transformation proceeded by using iron(III) chloride FeCl3 as a mild oxidant via the intramolecular radical addition to the allyl group followed by the second radical addition to the phenyl group.
منابع مشابه
Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone.
Unprecedented domino oxidative cyclization reactions of unprotected 2-alkynylanilines to give functionalized 4H-benzo[d][1,3]oxazin-4-one or benzisoxazole derivatives in moderate to good yields are achieved by silver vs. gold selective catalysis. The search for the optimal reaction conditions revealed the divergent catalytic activity of NaAuCl4·H2O and AgNO3.
متن کاملFe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for cyclization of 2- aminochalcones to 2- aryl-2,3- dihydroquinolin- 4(1H)- ones
Silica ferric hydrogensulfate is an efficient heterogeneous catalyst for the cyclization of 2- aminochalcones to the corresponding 2,3-dihydroquinolin- 4(1H)-ones. This intramolecular aza Michael reaction was carried out in high yields using chalcones bearing of electron donating and electron withdrawing groups. The catalyst is reusable without significant decreases in its activity after four t...
متن کاملFe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for cyclization of 2- aminochalcones to 2- aryl-2,3- dihydroquinolin- 4(1H)- ones
Silica ferric hydrogensulfate is an efficient heterogeneous catalyst for the cyclization of 2- aminochalcones to the corresponding 2,3-dihydroquinolin- 4(1H)-ones. This intramolecular aza Michael reaction was carried out in high yields using chalcones bearing of electron donating and electron withdrawing groups. The catalyst is reusable without significant decreases in its activity after four t...
متن کاملEnantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis.
The first catalytic enantioselective Prins cyclization is disclosed. The reaction is catalyzed by the combination of a chiral BINOL-derived bis-phosphoric acid and CuCl. The process consists of a tandem Prins/Friedel-Crafts cyclization that affords the hexahydro-1H-benzo[f]isochromenes products with three new contiguous stereogenic centers in high yields, and good enantio- and excellent diaster...
متن کاملPalladium(0)-catalyzed cyclization of 1,6-diyn-3-yl carbonates with a nucleophilic functionality: efficient synthesis of polycyclic benzo[b]fluorene derivatives via allene intermediates.
We report in this paper an interesting tandem reaction involving sequential palladium(0)-catalyzed decarboxylation of diynylic carbonates, intramolecular nucleophilic cyclization and Schmittel reaction, which provides a facile method for the synthesis of a variety of polycyclic benzo[b]fluorene derivatives from easily accessible starting materials.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره شماره
صفحات -
تاریخ انتشار 2017