178210-71-4Relevant academic research and scientific papers
Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
supporting information, p. 7540 - 7544 (2021/10/12)
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
Enantioselective Intramolecular Copper-Catalyzed Borylacylation
Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
supporting information, p. 13927 - 13930 (2018/10/02)
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
supporting information, p. 2226 - 2229 (2015/05/13)
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
Low-valent titanium induced indole formation: Syntheses of secofascaplysin, indolopyridocoline and an endothelin-receptor-antagonist
Fuerstner, Alois,Ernst, Andreas,Krause, Helga,Ptock, Arne
, p. 7329 - 7344 (2007/10/03)
The versatility of a titanium-induced reductive oxo-amide coupling reaction is illustrated by the syntheses of the alkaloids secofrascaplysin 8 and indolopyridocoline 14 as well as by an efficient and flexible approach to the arylated indole-2-carboxylic acid 4, which has recently been disclosed as a promising endothelin-receptor-antagonist. Depending on the particular substitution pattern in the substrates, either pre-formed titanium on graphite or low-valent titanium formed in situ ('instant conditions') are the preferred coupling agents for reductive heterocycle syntheses of this type.
