68524-30-1Relevant articles and documents
Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification
Huy, Peter H.,Mbouhom, Christelle
, p. 7399 - 7406 (2019/08/20)
A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.
HETEROCYCLIC COMPOUNDS WITH WORKING MEMORY ENHANCING ACTIVITY
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, (2016/02/29)
The present invention relates to a chemical compound having the general formula (I): wherein R1 and R2 are, equal or independently, aryl, heteroaryl; wherein RTA is a 2-1,3-, or 4- 1,3- or 5-1,3-thiazole ring and its use in for improving; the short term memory and/or the working memory.
One-pot parallel synthesis of alkyl sulfides, sulfoxides, and sulfones
Bogolubsky, Andrey V.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Ostapchuk, Eugeniy N.,Rudnichenko, Alexander V.,Dmytriv, Yurii V.,Bondar, Anna N.,Zaporozhets, Olga A.,Pipko, Sergey E.,Doroschuk, Roman A.,Babichenko, Liudmyla N.,Konovets, Anzhelika I.,Tolmachev, Andrey
, p. 348 - 354 (2015/06/22)
A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H2O2 or H2O2-(NH4)2MoO4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30-300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures.
