467217-77-2Relevant academic research and scientific papers
Practical Synthesis of β-Ketothioesters by Acid-Catalyzed Hydrolysis of Ketene N,S-Acetals with Amino as the Leaving Group
Xu, Qi,Zheng, Baihui,Pan, Ling,Liu, Qun,Li, Yifei
, p. 3704 - 3710 (2019)
A Novel, general, and highly efficient methodology for the synthesis of β-ketothioesters from ketene N,S-acetals has been developed. In this acid-catalyzed reaction, the amino group, including both alkylamino and arylamino groups, of α-oxo ketene N,S-acetals can be easily displaced in the presence of H2O as nucleophile (hydrolysis) instead of the alkylthiol group reported. This new method is simple and practical. A series of β-ketothioesters were prepared in high yields with broad tolerance of substrates under mild reaction conditions.
DBSA-catalyzed hydrolysis of chain α-oxo ketene dithioacetals in water: Aqueous synthesis of β-ketothioesters
Qi, Fei,Yu, Hai-Feng,Wang, Yue-Nan,Lv, Ye,Li, Ya-Xi,Han, Lu,Wang, Rong,Feng, Xi-Ning
supporting information, p. 2220 - 2224 (2017/11/15)
In this paper, we wish to report an environment friendly synthetic method for β-ketothioesters from a dodecylbenzenesulfonic acid (DBSA)-catalyzed hydrolysis reaction of chain α-oxo ketene dithioacetals in water. It was shown that the hydrolysis reaction of chain α-oxo ketene dithioacetals could efficiently occur in the presence of 7.5 mol% DBSA at 100 °C in water, affording the desired β-keto thioesters in excellent yields.
One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate
Bagley, Mark C.,Chapaneri, Krishna,Dale, James W.,Xiong, Xin,Bower, Justin
, p. 1389 - 1399 (2007/10/03)
(Chemical Equation Presented) The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.
