339087-31-9Relevant academic research and scientific papers
Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization
Campbell, Mark W.,Yuan, Mingbin,Polites, Viktor C.,Gutierrez, Osvaldo,Molander, Gary A.
supporting information, p. 3901 - 3910 (2021/04/06)
Alkenes, ethers, and alcohols account for a significant percentage of bulk reagents available to the chemistry community. The petrochemical, pharmaceutical, and agrochemical industries each consume gigagrams of these materials as fuels and solvents each year. However, the utilization of such materials as building blocks for the construction of complex small molecules is limited by the necessity of prefunctionalization to achieve chemoselective reactivity. Herein, we report the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provides a new, more atom-economic outlook for organic synthesis. Through detailed experimental and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered.
Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko
, p. 1143 - 1156 (2017/02/18)
The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.
2-Aryl(pyrrolidin-4-yl)acetic acids are potent agonists of sphingosine-1-phosphate (S1P) receptors
Yan, Lin,Budhu, Richard,Huo, Pei,Lynch, Christopher L.,Hale, Jeffrey J.,Mills, Sander G.,Hajdu, Richard,Keohane, Carol A.,Rosenbach, Mark J.,Milligan, James A.,Shei, Gan-Ju,Chrebet, Gary,Bergstrom, James,Card, Deborah,Mandala, Suzanne M.
, p. 3564 - 3568 (2007/10/03)
A series of 2-aryl(pyrrolidin-4-yl)acetic acids were synthesized and their biological activities were evaluated as agonists of S1P receptors. These analogs were able to induce lowering of lymphocyte counts in the peripheral blood of mice and were found to
2-(ARYL)AZACYCLYLMETHYL CARBOXYLATES, SULFONATES, PHOSPHONATES, PHOSPHINATES AND HETEROCYCLES AS S1P RECEPTOR AGONISTS
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Page/Page column 33, (2008/06/13)
The present invention encompasses compounds of Formula I: as well as the pharmaceutically acceptable salts thereof. The compounds are S1P1/Edg1 receptor agonists and thus have immunosuppressive, anti-inflammatory and hemostatic activities by mo
Photosubstitution reaction of cyanoaromatics with aliphatic amides
Tsuji, Moriya,Higashiyama, Kimio,Yamauchi, Takayasu,Kubo, Hajime,Ohmiya, Shigeru
, p. 1027 - 1032 (2007/10/03)
Photoreaction of p- (4) and o-dicyanobenzene (6) and 4-cyanopyridine (7) with formamides (1 and 3) and 1-alkyl-2-pyrrolidone (2) produced α-aryl amides (10, 12, 13, 16, and 17). This reaction is attributable to a substitution of the carbon adjacent to the nitrogen of the amide for the cyano group in 4 and 7.
