1083003-99-9Relevant academic research and scientific papers
Base-mediated hydroamination of propargylamine: A regioselective intramolecular 5-exo-dig cycloisomerization en route to imidazole-2-thione
Ranjan, Alok,Yerande, Ragini,Wakchaure, Prasad B.,Yerande, Swapnil G.,Dethe, Dattatraya H.
, p. 5788 - 5791 (2014)
An intramolecular transition-metal-free base-mediated hydroamination of propargylamine with isothiocyanates has been achieved. This atom-economical, regioselective intramolecular 5-exo-dig cycloisomerization was utilized for the one-pot synthesis of diversely substituted imidazole-2-thione and spiro-cyclic imidazolidine-2-thione. The reaction goes to completion at room temperature via propargylthiourea and 65-97% isolated yields were obtained.
Thiol–Yne Coupling of Propargylamine under Solvent-Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin-2-ylideneamine
Ranjan, Alok,Deore, Abhijit S.,Yerande, Swapnil G.,Dethe, Dattatraya H.
, p. 4130 - 4139 (2017)
Thiol–yne coupling of propargylamine with isothiocyanate has been developed under metal- and solvent-free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5-exo-dig cyclization to give thiazolidin-2-ylideneamine. A through-bond anion relay reaction occurs by attack of the sulfur (not the nitrogen) atom on the alkyne in a highly regioselective manner at ambient temperature. Wide varieties of thiazolidin-2-ylideneamine derivatives were formed in excellent yields.
Facile and diverse microwave-assisted synthesis of secondary propargylamines in water using CuCl/CuCl2
Trang, Tran Thi Thu,Ermolat'ev, Denis S.,Van Der Eycken, Erik V.
, p. 28921 - 28924 (2015/04/14)
A highly efficient microwave-assisted three-component reaction between an aldehyde, a primary amine and an alkyne was developed using an inexpensive Cu(i)/Cu(ii) catalytic system and water as solvent. A wide range of diversely substituted secondary propargylamines was prepared in good and high yields within a short period of time.
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
A regiospecific approach to N-alkylpyrazoles and the derived N-oxides using 5-endo-dig cyclisations of alkynyl nitrosamines
Hayes, Simon J.,Knight, David W.,O'Halloran, Mark,Pickering, Stuart R.
experimental part, p. 2188 - 2190 (2009/04/07)
5-endo-dig Cyclisations of N-nitroso derivatives of homopropargylic amines, catalysed by silver nitrate on silica gel proceed smoothly at ambient temperature in chlorinated solvents to give essentially quantitative yields of the corresponding pyrazole-N-oxides, deoxygenation of which gives excellent yields of the related N-alkylpyrazoles in a regiospecific manner. Georg Thieme Verlag Stuttgart.
