77213-87-7Relevant articles and documents
Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols
Maurya, Chandra Kant,Gupta, Pradeep Kumar
, p. 1649 - 1651 (2017/08/11)
In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.
Routes of Synthesis of Carbapenems for Optimizing Both the Inactivation of l, d -Transpeptidase LdtMt1 of Mycobacterium tuberculosis and the Stability toward Hydrolysis by β-Lactamase BlaC
Iannazzo, Laura,Soroka, Daria,Triboulet, Sébastien,Fonvielle, Matthieu,Compain, Fabrice,Dubée, Vincent,Mainardi, Jean-Luc,Hugonnet, Jean-Emmanuel,Braud, Emmanuelle,Arthur, Michel,Etheve-Quelquejeu, Mélanie
, p. 3427 - 3438 (2016/05/19)
Combinations of β-lactams of the carbapenem class, such as meropenem, with clavulanate, a β-lactamase inhibitor, are being evaluated for the treatment of drug-resistant tuberculosis. However, carbapenems approved for human use have never been optimized for inactivation of the unusual β-lactam targets of Mycobacterium tuberculosis or for escaping to hydrolysis by broad-spectrum β-lactamase BlaC. Here, we report three routes of synthesis for modification of the two side chains carried by the β-lactam and the five-membered rings of the carbapenem core. In particular, we show that the azide-alkyne Huisgen cycloaddition reaction catalyzed by copper(I) is fully compatible with the highly unstable β-lactam ring of carbapenems and that the triazole ring generated by this reaction is well tolerated for inactivation of the l,d-transpeptidase LdtMt1 target. Several of our new carbapenems are superior to meropenem both with respect to the efficiency of in vitro inactivation of LdtMt1 and reduced hydrolysis by BlaC.
Preparations et heterocyclisations nucleophiles de thiols acetyleniques
Dupuy, Claude,Surzur, Jean-Marie
, p. 353 - 360 (2007/10/02)
Acetylenic thiols HCC(CH2)nSH 1a and HCCCH2Y(CH2)2SH 1b, isolated or prepared in situ from the corresponding thiouronium salts, have been treated with alkali to induce cyclization by intramolecular nucleophilic addition of the thiolate to the triple bond.Starting from the thiol 1a (n = 2) we only isolated thiacyclopent-2-ene 2a, which results from addition to the terminal carbon of the triple bond (yield 45 percent).Higher homologues 1a (n = 3,4), on the other hand, exclusively led to the heterocyclic products 3a resulting from addition to the non-terminal carbon of the triple bond.The best yield was obtained with 1a (n = 3), which led to 2-methylenethiacyclopentane 3a (n = 3) with a 59 percent yield.With the thiol 1a (n = 4), the yield was only 20 percent for 2-methylenethiacyclohexane 3a (n = 4), and with 1a (n = 5) only polymers were formed.When Y = S or N-n-Bu, the substrates 1b behaved like their carbon homologues 1a (n = 3) : yields were in the same range, and the seven-membered heterocycle 2b resulting from attack on the terminal carbon of the triple bond could not be detected.On the other hand, substance 1b (Y = O) mainly led to the seven-membered ring compound 2b.Furthermore, the presence of the heteroatom Y enhanced the possibility of prototropic rearrangement of the triple bond, leading to the new heterocycle 4b in appreciable amounts for Y = O,S.Generally speaking, acetylenic thiolates behave similarly to acetylenic alkoxides, and the same tentative interpretations can be put forward to account for the results obtained.
