73508-14-2Relevant articles and documents
Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines
Cimarelli, Cristina,Navazio, Federica,Rossi, Federico V.,Del Bello, Fabio,Marcantoni, Enrico
, p. 2387 - 2396 (2019/05/27)
Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.
Modular Access to Tetrasubstituted Imidazolium Salts through Acid-Catalyzed Addition of Isocyanides to Propargylamines
Ghashghaei, Ouldouz,Revés, Marc,Kielland, Nicola,Lavilla, Rodolfo
supporting information, p. 4383 - 4388 (2015/07/27)
Propargylamines, prepared through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. The key step of the mechanism involves the generation of an amidine intermediate, from the isocyanide insertion into the N-H bond of the propargylamine, which in situ evolves by cyclization upon the alkyne moiety. The scope of the process is analyzed and only shows restrictions for aliphatic amines, whereas it is quite general regarding the aldehyde, alkyne and isocyanide inputs. The protocol allows the preparation of a wide array of adducts, tandem one-pot processes being also feasible. Mechanistic studies using selected substrates have been used to determine the profile of the reaction and some substitution and functional group limitations. Some post-synthetic transformations of the imidazolium salts have been performed as well. Propargylamines, synthesized through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. Tandem one-pot protocols allow direct access to these adducts from the commercially available inputs.
Efficient microwave-assisted synthesis of secondary alkylproparglamines by using A3-coupling with primary aliphatic amines
Bariwal, Jitender B.,Ermolat'Ev, Denis S.,Van Der Eycken, Erik V.
supporting information; experimental part, p. 3281 - 3284 (2010/06/19)
(Chemical Equation Presented) Three-component coupling reaction: An efficient, microwave-assisted, CuIcatalysed A3-coupling reaction with primary aliphatic amines that gives access to secondary propargylamines is described (see schem
