The NbCl5–EtMgBr-catalyzed reaction of N,N-disubstituted 2-alkynylamines with Et2Zn followed by hydrolysis or deuterolysis affords (2Z)-alkenylamines (reduction products of alkyne) in high yields.
The reaction of alkyl-and aryl-substituted carboxylic acids with primary and secondary amines under the action of 0.2 equiv. TaCl 5 leads to selective formation of carboxylic acid amides of various structures. TaCl 5 -catalyzed formation of amides was demonstrated to proceed equally selectively both in toluene and methylene chloride, hexane, diethyl ether and 1,4-dioxane solutions.
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.
The Ti(O-iPr)4 and EtMgBr-catalyzed regio and stereoselective carbocyclization of N-allyl-substituted 2-alkynylamines with Et2Zn, followed by deuterolysis or hydrolysis, affords the corresponding methylenepyrrolidine derivatives in high yields.
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