6833-29-0Relevant academic research and scientific papers
Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow
Folgueiras-Amador, Ana A.,Qian, Xiang-Yang,Xu, Hai-Chao,Wirth, Thomas
supporting information, p. 487 - 491 (2017/12/15)
A catalyst- and supporting electrolyte-free method for electrochemical dehydrogenative C?S bond formation in continuous flow has been developed. A broad range of N-arylthioamides have been converted to the corresponding benzothiazoles in good to excellent yields and with high current efficiencies. This transformation is achieved using only electricity and laboratory grade solvent, avoiding degassing or the use of inert atmosphere. This work highlights three advantages of electrochemistry in flow, which is (i) a supporting electrolyte-free reaction, (ii) an easy scale-up of the reaction without the need for a larger reactor and, (iii) the important and effective impact of having a good mixing of the reaction mixture, which can be achieved effectively with the use of flow systems. This clearly improves the reported methods for the synthesis of benzothiazoles.
Fixation of heterocumulenes, II. - A study on the reaction of lithiated allyl systems with CO2, isocyanates and isothiocyanates
Piffl, Michaela,Weston, Jennie,Anders, Ernst
, p. 2851 - 2859 (2007/10/03)
The regioselectivity of the reaction of 1-(thiophenyl)- (Li-6), 1-(phenylsulfinyl)- (Li-12), 1-(phenylsulfonyl)- (Li-15) and 1-(diethoxyphosphoryl)allyllithium (Li-18) with CO2, PhNCO and PhNCS is investigated. Carboxylation of the allyl sulfide 6 and the allyl sulfoxide 12 proceeds with low regioselectivity. On the other hand, an exclusive γ-selectivity is achieved for reactions of CO2 with Li-15 and Li-18. Both carboxylations are reversible and can be directed to give a-products by using low temperature workup (0 °C). In contrast to CO2, PhNCO reacts with the allylic compounds investigated here to give amides with a high degree of regioselectivity: α-Attack is found for the sulfide 6 and the sulfone 15 whereas the reaction occurs at the γ-terminus for the sulfoxide 12 and the phosphonate 18. Exclusive α-attack is observed for all sulfur-substituted allyllithium compounds on reaction with PhNCS. In contrast to this, reaction of the phosphonate 18 with PhNCS yields exclusively the γ-product.
Reactions des organolithiens et des reactifs de Grignard avec les N-phenyl imidothioesters et les dithioesters α-insatures
El-Jazouli, Mustapha,Masson, Serge,Thuillier, Andre
, p. 875 - 882 (2007/10/02)
The reactivity of α-unsaturated N-phenyl imidothioesters towards organomagnesium and lithium compounds was studied.From an α or β-non ramified imidothioester (methyl N-phenyl 2-butenimidothioate) 1,4-additions were observed with alkyl-, vinyl- and aryl-Grignard reagents, alkyllithium and lithiated limonene, and with benzenethiolate and benzenesulfinate anions.After sulfhydrolysis, new β-ramified or functionalized dithioesters were isolated and one of them was used in a synthesis of 2,6-dimethyl-1,7-octadiene-4-one.A 1,2-addition, with inversion of the allylic chain, was observed with allylic Grignard reagents, followed by a second 1,2-addition to the imine formed after elimination of magnesium methylthiolate.This double addition was not observed with prenylmagnesium bromide, the reaction of which with methyl 3-methyl N-phenyl 2-butenimidothioate led, after hydrolysis, to artemisia ketone.The regoiselectivities of the additions of organometallics to methyl 2-butenedithioate (prepared in situ from methyl phenylsulfonyl-3 butanedithioate) were also examined and they appeared completely different to those observed with the corresponding imidothioester; a thiophilic addition was the first step in the reaction of methyllithium or ethylmagnesium bromide and 1,4-γ-additions were observed with allylic Grignard reagents.
SYNTHESIS AND PROPERTIES OF THIOACYLANILIDE FLOTATION REAGENT.
Ryaboi,Poroshina,Starovoitov,Gnatyuk,Malii,Polyanskii
, p. 1082 - 1084 (2007/10/02)
Investigations have shown that a compound with a thioamide group from the thioacylanilide class, of the following structure, is an effective flotation reagent. With the aim of using this reagent in ore flotation, the authors studied the conditions of its synthesis and some of its physicochemical properties. The method based on the reaction of acylanilides with tetraphosphorus decasulfide is the most suitable for industrial operation. Experimental data show that by the use of a small excess of acylanilide it is possible to obtain a high yield of a product having the required viscosity and to dispense with solvents. The physicochemical properties of the reagent have been investigated.
Benzothiazocine and benzothiazonine derivatives and use
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, (2008/06/13)
Benzothiazocine and benzothiazonine derivatives of formula (I): STR1 in which: R1, R2 and R3 are the same or different and each represents a hydrogen atom or an alkyl group; X1 and X2 are the same or
