91962-59-3Relevant academic research and scientific papers
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.
Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange
Benischke, Andreas D.,Anthore-Dalion, Lucile,Berionni, Guillaume,Knochel, Paul
supporting information, p. 16390 - 16394 (2017/11/28)
Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at ?50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.
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.
Direct asymmetrie catalytic thienylaluminum addition to ketones: A concise approach to the synthesis of (S)-tiemonium iodide
Biradar, Deepak B.,Zhou, Shuangliu,Gau, Han-Mou
supporting information; experimental part, p. 3386 - 3389 (2009/12/01)
A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.
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.
Photochemical reactions of Thienyl-, Bithienyl-, Terthienyl- and Thienylaroyl-methanols
Krishnaswamy, N. R.,Kumar, Ch. Siva Sai Kamana,Prasanna, S.
, p. 1801 - 1830 (2007/10/02)
Photochemical reactions of some thienyl-, bithienyl-, terthienyl- and thienylaroyl-methanols were studied in the neat state as well as in solvents like methanol and benzene.The terthienylmethanols were found to be susceptible to photo-sensitized oxidation which was inhibited by singlet oxygen quenchers.The photoproducts were isolated, characterised by spectroscopic methods and in some cases by synthesis.
