36838-59-2Relevant articles and documents
Copper-catalyzed hydroamination of alkynes with aliphatic amines: Regioselective access to (1 E,3 E)-1,4-disubstituted-1,3-dienes
Bahri, Janet,Jamoussi, Bassem,Van Der Lee, Arie,Taillefer, Marc,Monnier, Florian
, p. 1224 - 1227 (2015)
Copper-catalyzed hydroamination of aromatic or heteroaromatic alkynes with cyclic secondary aliphatic amines undergoes generation of an enamine-type intermediate. The latter is transformed in situ via a coupling reaction with a second molecule of alkyne to afford regioselectively (1E,3E)-1,4-disubstituted-1,3-dienes with the formation of C-N, C-C, and C-H bonds.
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.
Synthesis of Chromone-Containing Allylmorpholines through a Morita–Baylis–Hillman-Type Reaction
Chernov, Nikita M.,Shutov, Roman V.,Barygin, Oleg I.,Dron, Mikhail Y.,Starova, Galina L.,Kuz'mich, Nikolay N.,Yakovlev, Igor P.
supporting information, p. 6304 - 6313 (2018/11/10)
The first example of an unusual addition of chromone-substituted acrylic acid to enamines is described. The process shows high versatility concerning both enamines and chromones. The reaction is catalyzed by tertiary amines and is highly likely of Morita–
Transformation of Amides into Highly Functionalized Triazolines
Slagbrand, Tove,Volkov, Alexey,Trillo, Paz,Tinnis, Fredrik,Adolfsson, Hans
, p. 1771 - 1775 (2017/08/09)
Triazoles and triazolines are important classes of heterocyclic compounds known to exhibit biological activity. Significant focus has been given to the development of synthetic approaches for the preparation of triazoles, and they are today easily obtainable through a large variety of protocols. The number of synthetic procedures for the formation of triazolines, on the other hand, is limited and further research in this field is required. The protocol presented here gives access to a broad scope of 1,4,5-substituted 1,2,3-triazolines through a one-pot transformation of carboxamides. The two-step procedure involves a Mo(CO)6-catalyzed reduction of tertiary amides to afford the corresponding enamines, followed by in situ cycloaddition of organic azides to form triazolines. The amide reduction is chemoselective and allows for a wide variety of functional groups such as esters, ketones, aldehydes, and imines to be tolerated. Furthermore, a modification of this one-pot procedure gives access to the corresponding triazoles. The chemically stable amide functionality is demonstrated to be an efficient synthetic handle for the formation of highly substituted triazolines or triazoles.
