Thiol–Yne Coupling of Propargylamine under Solvent‐Free Conditions by Bond Anion Relay Chemistry: An Efficient Synthesis of Thiazolidin‐2‐ylideneamine

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....

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Bibliographic Details
Published in:European journal of organic chemistry 2017-08, Vol.2017 (28), p.4130-4139
Main Authors: Ranjan, Alok, Deore, Abhijit S., Yerande, Swapnil G., Dethe, Dattatraya H.
Format: Article
Language:English
Subjects:
Alkynes
Ambient temperature
Anion relay chemistry
Anions
Chemical synthesis
Coupling
Cyclization
Heterocycles
Relay
Solvents
Sulfur
Synthetic methods
Thiazolidin‐2‐ylideneamine
Thiol‐ynes
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Summary: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. 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. Wide varieties of thiazolidin‐2‐ylideneamine derivatives were formed in excellent yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700603