6052-80-8Relevant academic research and scientific papers
Tetrabutylammonium tribromide (TBATB) as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds
Gopinath, Rangam,Haque, Sk. Jiaul,Patel, Bhisma K.
, p. 5842 - 5845 (2002)
Acyclic and cyclic acetals of various carbonyl compounds were obtained in excellent yields under a mild reaction condition in the presence of trialkyl orthoformate and a catalytic amount of tetrabutylammonium tribromide (TBATB) in absolute alcohol. Chemoselective acetalization of an aldehyde in the presence of ketone, unsymmetrical acetal formation, shorter reaction times, mild reaction conditions, the stability of acid-sensitive protecting groups, high efficiencies, facile isolation of the desired products, and the catalytic nature of the reagent make the present methodology a practical alternative.
Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
supporting information, p. 3459 - 3464 (2021/05/24)
N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
Sequence stereoisomerism in calixarene-based pseudo[3]rotaxanes
Talotta, Carmen,Gaeta, Carmine,Pierro, Teresa,Neri, Placido
supporting information; scheme or table, p. 2098 - 2101 (2011/06/21)
Two calix[6]arene directional wheels can be ordered in the right stereosequence by their through-the-annulus threading with a rationally designed bis(benzylalkylammonium) axle. These stereoisomeric pseudo[3]rotaxanes can be considered as a minimal "inform
Bismuth compounds in organic synthesis: Synthesis of dioxanes, dioxepines, and dioxolanes catalyzed by bismuth(III) triflate
Podgorski, Daniel M.,Krabbe, Scott W.,Le, Long N.,Sierszulski, Paul R.,Mohan, Ram S.
experimental part, p. 2771 - 2775 (2010/10/02)
A simple method for the synthesis of 1,3-dioxolanes from carbonyl compounds has been developed using 1,2-bis(trimethylsilyloxy)ethane in the presence of bismuth(III) triflate as a catalyst. The bismuth(III) triflate catalyzed synthesis of a range of dioxanes and dioxepines has also been developed. In these latter cases, the carbonyl compound is treated with a diol, and triethyl orthoformate is used as a water scavenger. All these methods avoid the use of a Dean-Stark trap. Georg Thieme Verlag Stuttgart.
