95547-16-3Relevant academic research and scientific papers
A novel synthesis of β-ketosilanes via organoboranes
Bhat,Martinez,De Los Santos
, p. 6541 - 6544 (2000)
A convenient, novel synthesis of β-ketosilanes based on (Z)-1-bromo-1-alkenylboronate esters is developed. α-Bromo-(Z)-1-alkenylboronate esters readily available using literature procedures smoothly undergo a reaction with trimethylsilylmethyllithium in tetrahydrofuran to provide the corresponding 'ate' complexes. These 'ate' complexes will undergo intramolecular nucleophilic substitution reactions to afford the corresponding (E)-trisubstituted olefins containing trimethylsilylmethyl moiety. The oxidation of these intermediates with sodium acetate and hydrogen peroxide provides β-ketosilanes in good yields (63-75% yield). (C) 2000 Elsevier Science Ltd.
Design, synthesis, SAR and biological investigation of 3-(carboxymethyl)rhodanine and aminothiazole inhibitors of Mycobacterium tuberculosis Zmp1
Mori, Mattia,Deodato, Davide,Kasula, Mohan,Ferraris, Davide M.,Sanna, Adriana,De Logu, Alessandro,Rizzi, Menico,Botta, Maurizio
supporting information, p. 637 - 641 (2018/02/06)
Sixteen 3-(carboxymethyl)rhodanines, and twelve aminothiazoles as rhodanine-mimetics were designed, synthesized and tested as inhibitors of the Zmp1 enzyme from Mycobacterium tuberculosis (Mtb). Almost all rhodanines (5a–d, 5f–n, and 7a–b) exhibited Zmp1 inhibition with IC50 values in the range 1.3–43.9 μM, whereas only aminothiazoles 12b and 12d proved active with IC50 values of 41.3 and 35.7 μM, respectively. Structure-activity relationships (SAR) were coupled with molecular modeling studies to highlight structural determinants for Zmp1 inhibition. Moreover, rhodanines 5a and 5c induced 23.4 and 53.8% of Mtb growth inhibition in THP-1 infected cells, respectively, at the non-toxic concentration of 10 μg/ml. This work represents a step forward in targeting Zmp1 by small molecules.
Reaction of acylsilanes with sulfur ylides. Selective formation of silyl enol ethers or β-ketosilanes
Nakajima, Tadashi,Segi, Masahito,Sugimoto, Fumitosi,Hioki, Reiko,Yokota, Seiko,Miyashita, Kiyoshi
, p. 8343 - 8358 (2007/10/02)
The reaction of acylsilanes with sulfur ylides in THF results in the formation of the corresponding silyl enol ethers or β-ketosilanes. The relative ratio of these products varies with the ylide conditions and the stability of ylide used. It is noteworthy that silyl enol ethers were formed under the salt-free ylide conditions, and that β-ketosilanes were yielded in the presence of soluble inorganic salts in THF, selectively. The formation of both products would be interpreted in terms of the anionotropic and cationotropic rearrangements of silyl group in the reaction intermediate.
Selective formation of alkenes from trimethylsilylmethyl ketones and from acylsilanes
Fuerstner, Alois,Kollegger, Gerlinde,Weidmann, Hans
, p. 295 - 305 (2007/10/02)
Trimethylsilylmethyl ketones, readily available from acyl chlorides, undergo a Reformatsky-Peterson reaction sequence to give 3-alkenoates regioselectively.Acylsilanes, however, react with either zinc ester enolates or trimethylsilylmethylmagnesium chloride to give the corresponding tertiary alcohols which, depending on their structure, spontaneously undergo either elimination or a Brook rearrangement-Peterson olefination sequence.These reactions allow the selective formation of vinylsilanes.
Silicon-Directed Diene Synthesis
Brown, Paul A.,Bonnert, Roger V.,Jenkins, Paul R.,Lawrence, Nicholas J.,Selim, Mohammed R.
, p. 1893 - 1900 (2007/10/02)
A synthesis of 2-substituted-1,3-dienes is reported which uses silicon as a control element: eight aldehydes were converted into α-silyl ketones by treatment with trimethylsilylmethylmagnesium chloride and rapid Collins oxidation.Addition of vinylmagnesiu
A SILICON DIRECTED DIENE SYNTHESIS
Brown, Paul A.,Bonnert, Roger V.,Jenkins, Paul R.,Selim, Mohammed R.
, p. 693 - 696 (2007/10/02)
A convenient method for the conversion of a series of aldehydes into substituted dienes is reported which uses silicon as a control element.
REGIOSELECTIVE PREPARATION OF KINETIC TRIMETHYLSILYL ENOL ETHERS FROM β-KETO SILANES
Yamamoto, Yohsuke,Ohdoi, Keisuke,Nakatani, Masayuki,Akiba, Kin-ya
, p. 1967 - 1968 (2007/10/02)
Kinetic trimethylsilyl enol ethers were prepared regioselectively by the two-step method, i.e., trimethylsilyl triflate catalyzed rearrangement of β-keto silanes which were prepared from trimethylsilylmethylcopper and acid chlorides.
