102877-79-2Relevant academic research and scientific papers
Simple methodology for the preparation of amino alcohols from amino acid esters using nabh4-methanol in THF
Goncalves,Pinheiro,Da Silva,Da Costa,Kaiser,De Souza
, p. 1276 - 1281 (2011)
Amino alcohols constitute a very useful and versatile class of organic compounds, with important applications in synthetic and medicinal chemistry. However, in most of the procedures described in the literature for the obtainment of these compounds, considerable limitations can be found, such as drastic conditions, long time reactions, poor yields, and purification problems. The present article describes a methodology that gives amino alcohols and N-protected amino alcohols based on the reduction of amino acid esters under mild conditions, employing NaBH4 in the presence of methanol. The reactions occurred in a short time (15-20min) and provide yields of 50-95%.
New solid-supported reagents (SSRs) for selective acylation of amines
Botta, Maurizio,Corelli, Federico,Petricci, Elena,Seri, Catia
, p. 369 - 377 (2002)
The pyrimidine linker (4) was prepared by solid phase synthesis starting from Merrifield resin. Acylation of 4 with different acyl chlorides gave polymer-bound 4-acyloxypyrimidines (2a-c), which proved to be useful solid-supported reagents for the selecti
An improved synthesis of solid-supported reagents (SSRs) for selective acylation of amines by microwave irradiation
Petricci, Elena,Botta, Maurizio,Corelli, Federico,Mugnaini, Claudia
, p. 6507 - 6509 (2002)
Microwave-assisted acylation of a solid-supported pyrimidine linker with different acyl chlorides gave polymer-bound 4-acyloxypyrimidines, which in turn were used as SSRs for rapid and selective acylation of amines under microwave irradiation.
N-acylcarbazole as a selective transamidation reagent
Kang, Bubwoong,Kuse, Masaki,Okamura, Hironori,Sakai, Asumi,Satoh, Tetsuya,Shinada, Tetsuro,Yasuno, Yoko
, p. 993 - 999 (2020/09/22)
N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.
Chemoselective Synthesis of α-Amino-α-cyanophosphonates by Reductive Gem-Cyanation-Phosphonylation of Secondary Amides
Chen, Ting-Ting,Wang, Ai-E,Huang, Pei-Qiang
supporting information, p. 3808 - 3812 (2019/05/24)
A novel approach to α-amino-α-cyanophosphonates has been developed. The method features a Tf2O-mediated reductive geminal cyanation/phosphonylation of secondary amides. Mild reaction conditions, high bond-forming efficiency, inexpensive readily available starting materials, and good to excellent yields with wide functional group compatibility constitute the main advantages of this method. The protocol can be run on a gram scale.
Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines
Mollo, María C.,Orelli, Liliana R.
supporting information, p. 6116 - 6119 (2016/12/09)
The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.
Laccase/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO): An efficient catalytic system for selective oxidations of primary hydroxy and amino groups in aqueous and biphasic media
Díaz-Rodríguez, Alba,Martínez-Montero, Lía,Lavandera, Iván,Gotor, Vicente,Gotor-Fernández, Vicente
supporting information, p. 2321 - 2329 (2014/07/21)
Copper salts/2,2,6,6-tetramethylpiperidinoxyl radical (TEMPO) catalytic systems enable efficient aerobic oxidations of primary alcohols but they generally show a reduced reactivity in aqueous medium. Herein, we report an oxidative catalytic system composed of Trametes versicolor laccase and TEMPO, which is able to work in buffer solutions at room temperature using ambient air. Although this catalytic system displays great efficiency in aqueous systems, the addition of methyl tert-butyl ether allows the reduction of TEMPO loading, also enhancing the solubility of hydrophobic compounds. This practical methodology promotes the chemoselective aerobic oxidation of hydroxy or amino groups, leading to interesting organic derivatives such as aldehydes, lactones, hemiaminals or lactams.
Targeting dopamine D3 and serotonin 5-HT1A and 5-HT2A receptors for developing effective antipsychotics: Synthesis, biological characterization, and behavioral studies
Brindisi, Margherita,Butini, Stefania,Franceschini, Silvia,Brogi, Simone,Trotta, Francesco,Ros, Sindu,Cagnotto, Alfredo,Salmona, Mario,Casagni, Alice,Andreassi, Marco,Saponara, Simona,Gorelli, Beatrice,Weikop, Pia,Mikkelsen, Jens D.,Scheel-Kruger, Jorgen,Sandager-Nielsen, Karin,Novellino, Ettore,Campiani, Giuseppe,Gemma, Sandra
, p. 9578 - 9597 (2015/01/09)
Combination of dopamine D3 antagonism, serotonin 5-HT1A partial agonism, and antagonism at 5-HT2A leads to a novel approach to potent atypical antipsychotics. Exploitation of the original structure-activity relationships resulted in the identification of safe and effective antipsychotics devoid of extrapyramidal symptoms liability, sedation, and catalepsy. The potential atypical antipsychotic 5bb was selected for further pharmacological investigation. The distribution of c-fos positive cells in the ventral striatum confirmed the atypical antipsychotic profile of 5bb in agreement with behavioral rodent studies. 5bb administered orally demonstrated a biphasic effect on the MK801-induced hyperactivity at dose levels not able to induce sedation, catalepsy, or learning impairment in passive avoidance. In microdialysis studies, 5bb increased the dopamine efflux in the medial prefrontal cortex. Thus, 5bb represents a valuable lead for the development of atypical antipsychotics endowed with a unique pharmacological profile for addressing negative symptoms and cognitive deficits in schizophrenia.
Synthesis of 2-oxazolines and related N-containing heterocycles using [Et2NSF2]BF4 as a cyclodehydration agent
Pouliot, Marie-France,Angers, Laetitia,Hamel, Jean-Denys,Paquin, Jean-Fran?ois
supporting information; experimental part, p. 4121 - 4123 (2012/08/28)
The preparation of 2-oxazolines and related N-containing heterocycles from the corresponding hydroxyamides using XtalFluor-E ([Et2NSF 2s]BF4) as a cyclodehydration agent is described. A wide range of heterocycles are obtai
The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
supporting information; experimental part, p. 739 - 746 (2009/06/20)
β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
