91962-59-3Relevant articles and documents
A Diels–Alder/Ene Cascade Leading to 5-(Pyrrolidin-3-yl)thieno[3,2-e]isoindoles from Ketone-derived 2-Vinylthiophenes and N-Phenylmaleimide
Noland, Wayland E.,Huisenga, Matthew P.,Herzig, Ryan J.,Rosenow, John A.,Kim, Hoyeon,Kroll, Neil J.,Nesmelov, Andrei,Johnson, Benjamin T.,Duncan, Nathan S.,Ratanayanon, Jidapa,Yue, Ruixian A.,Xiong, Kenny,Ong, Bee K.,Vo, Diane T.,Klein, Nathan D.,Lang, Simon B.,Riley, Jacob K.,Daniels, Steven P.,Tritch, Kenneth J.
, p. 2698 - 2714 (2018/11/10)
In an extension of our prior work with indoles and pyrroles, the Diels–Alder chemistry of substituted 2-vinylthiophenes was explored, using N-phenylmaleimide as the dienophile. The dienes were prepared from thiophene in two steps by addition to various ketones, followed by dehydration (40–60% overall yields). Although most dienes were obtained as regioisomeric mixtures, the Diels–Alder-derived products were easily purified by chromatography. The main cycloaddition pathway was endo Diels–Alder addition followed by exo ene addition of a second molecule of dienophile (19–33% yields). Several products were desulfurized with Raney nickel (48–62% yields). Unfortunately, no thiophene-derived products showed the promising biological activity of the previously reported indole analogs.
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
Ylmaz, Mehmet
experimental part, p. 8255 - 8263 (2011/11/12)
Manganese(III) acetate based radical cyclization of various fluorinated 1,3-dicarbonyl compounds with 2-thienyl and 2-furyl substituted alkenes produced 3-trifluoroacetyl and 2-trifluoromethyl-dihydrofurans in good yields. The radical cyclizations of 2-methyl-5-[(E)-2-phenylvinyl]furan 2b and 2-[(E)-2-phenylvinyl]thiophene 2c led to the formations of 5-(5-methyl-2-furyl)- 4,5-dihydrofuran and 5-(2-thienyl)-4,5-dihydrofuran, respectively. In the reactions of 1,3-dicarbonyls with alkenes, 2-thienyl substituted alkenes formed 4,5-dihydrofurans in higher yields than 2-furyl substituted alkenes.
Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water
Xing, Dong,Guan, Bingtao,Cai, Guixin,Fang, Zhao,Yang, Liping,Shi, Zhangjie
, p. 693 - 696 (2007/10/03)
Oxidative cleavage of the C=C bond to afford ketone or aldehyde products with tert-butyl hydrogenperoxide (TBHP) as the oxidant can be catalyzed by AuCl with neocuproine (1) in water.
