445255-32-3Relevant academic research and scientific papers
NbCl5-Mg reagent system in regio-and stereoselective synthesis of (2Z)-alkenylamines and (3Z)-alkenylols from substituted 2-alkynylamines and 3-alkynylols
Dzhemilev, Usein M.,Gabdullin, Azat M.,Kadikova, Rita N.,Mozgovoj, Oleg S.,Ramazanov, Ilfir R.
, (2021/07/02)
The reduction of N,N-disubstituted 2-alkynylamines and substituted 3-alkynylols using the NbCl5 –Mg reagent system affords the corresponding dideuterated (2Z)-alkenylamine and (3Z)-alkenylol derivatives in high yields in a regio-and stereoselective manner through the deuterolysis (or hydrolysis). The reaction of substituted propargylamines and homopropargylic alcohols with the in situ generated low-valent niobium complex (based on the reaction of NbCl5 with magnesium metal) is an efficient tool for the synthesis of allylamines and homoallylic alcohols bearing a 1,2-disubstituted double bond. It was found that the well-known approach for the reduction of alkynes based on the use of the TaCl5-Mg reagent system does not work for 2-alkynylamines and 3-alkynylols. Thus, this article reveals a difference in the behavior of two reagent systems—NbCl5-Mg and TaCl5-Mg, in relation to oxygen-and nitrogen-containing alkynes. A regio-and stereoselective method was developed for the synthesis of nitrogen-containing E-β-chlorovinyl sulfides based on the reaction of 2-alkynylamines with three equivalents of methanesulfonyl chloride in the presence of stoichiometric amounts of niobium(V) chloride and magnesium metal in toluene.
AgNO2 as the NO Source for the Synthesis of Substituted Pyrazole N-Oxides from N-Propargylamines
Yuan, Bingxiang,Zhang, Fuming,Li, Zhuomei,Yang, Shenghua,Yan, Rulong
supporting information, p. 5928 - 5931 (2016/11/29)
A straightforward method for synthesizing the pyrazole N-oxides from N-propargylamines and AgNO2 through oxidation/cyclization reaction had been developed. AgNO2 was used as the NO source for the first time to synthesize pyrazole N-o
A simple method for the preparation of propargylamines using molecular sieve modified with copper(II)
Fodor, Anna,Kiss, Arpad,Debreczeni, Nora,Hell, Zoltan,Gresits, Ivan
experimental part, p. 4575 - 4581 (2010/11/19)
A new, heterogeneous, 4 A molecular sieve-supported copper(ii) catalyst was developed and was used successfully in the A3 coupling of alkynes, aldehydes and amines under simple reaction conditions.
Reusable polymer-anchored amino acid copper complex for the synthesis of propargylamines
Wang, Liang,Cai, Chun
experimental part, p. 538 - 541 (2009/04/06)
An amino acid was anchored to chloroacetylated polystyrene beads and the polymeric ligand containing N, O donor sites was treated with a solution of Cul to form the supported copper complex. The one-pot synthesis of propargylamines was then achieved efficiently via a three-component coupling of aldehydes, alkynes and amines using the supported copper catalyst under mild conditions. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity.
Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction
Bieber, Lothar W.,Da Silva, Margarete F.
, p. 8281 - 8283 (2007/10/03)
Terminal alkynes can be condensed with aqueous formaldehyde and primary or secondary amines to give secondary and tertiary propargylamines. The reaction is best carried out in DMSO under CuI catalysis. Terminal alkynes undergo mild and efficient aminomethylation with aqueous formaldehyde and secondary amines under CuI catalysis. In most cases high to nearly quantitative yields of tertiary propargylamines are obtained in DMSO solution at room temperature. Aromatic, aliphatic and silylated acetylenes as well as alkynols can be used. Primary amines are less reactive and satisfactory yields of secondary propargylamines are obtained only with phenylacetylene.
